Why Won't You Date Me? with Nicole Byer - How to Pull Rich Men (w/ Robby Hoffman)

Episode Date: February 28, 2025

Comedian Robby Hoffman (Host of Too Far) joins Nicole to discuss being 'Jewish school slutty,' how growing up poor gave her the skills to pull rich men, and the best time to sneak away to the bathroom on a date. She shares the story of how she ended up dating a Bachelorette star mid-'exploration,' her golden rule for relationships (one hot, one smart—no exceptions), and the time she was invited to a Juneteenth cookout.WATCH this episode on YouTube at youtu.be/kKrxnRu_zGkWrite to Nicole! Send your dirty messages to [e-mail] with the subject line "Dirty Message" and Nicole may read it in a future episode.Follow:YouTube: @WhyWontYouDateMePodcastTikTok: @whywontyoudatemepod Instagram: @nicolebyerX: @nicolebyerNicole's book, #VERYFAT #VERYBRAVE: indiebound.org/book/9781524850746To support this podcast, check out our sponsors & get discounts:Alma: There’s no replacement for human connection. Better with people. Better with Alma. Visit helloalma.com/DATEME to get started and schedule a free consultation today.Dipsea: Right now, listeners of this show can get an extended 30-day free trial! Just go to DipseaStories.com/DATEME to start your free trial.Equip: To learn more about Equip's virtual eating disorder treatment, visit Equip.Health/dateme.NordVPN: Get the exclusive NordVPN deal now at nordvpn.com/DATEME Try risk-free with the 30-day money-back guarantee!Self-Conscious with Chrissy Teigen: The new wellness podcast from Audible. Go to Audible.com/Chrissypodcast and start listening today.Audience Survey: ​​Go to GUM.FM/DATEME to fill out our audience survey.View all of our sponsors and discounts codes at wwydm.notion.site/sponsors.This is a Headgum podcast. Follow Headgum on Twitter, Instagram, and Tiktok. Advertise on Why Won't You Date Me? via Gumball.fm.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Love the podcast? You'll love seeing even more of it on video! Watch this full episode on YouTube. Just check the description for the link. Subscribe so you don't miss out. New video episodes drop every Friday. Get the Angel Rees special at McDonald's now. Let's break it down. My favorite barbecue sauce, American cheese, crispy bacon, pickles, onions, and a sesame seed bun, of course. And don't forget the fries and a drink. Sound good? Ba-da-ba-ba-ba. I participate in restaurants for a limited time. Now, you know, I don't want to get too much into this and toot my own horn,

but I've been invited to a cookout or two. Have you? I actually have. Can I tell you, this, this, this, I probably wouldn't say if I wasn't so comfortable with you. Uh-huh. Which I shouldn't even be that comfortable with you. I don't know why I've always had a comfort with you.

I feel like I'm a person where you can just talk to me. You know what, I guess I knew you before I knew you because my little sister, your hoodies, has always been your biggest fan. And I made a video for her, right? Yes, yes, yeah. And she, by the way, loves your necklace. Thank you. It was a topic of discussion at a show we did.

Yeah, she's very happy for you. Tell her thank you. Yes, shout out to Your Hores. Here it is, it's happening for you. But this was the first Juneteenth. I'm sharing this story. I didn't know of Juneteenth. But I was living in a,

after a big breakup I had like six years ago, five years ago, six is five, I decided to move. I decided I'm just going to get a little studio with one chair. And I'm just not like, I'm just going to stack the money. Like I'm just not going to. Oh, okay.

Because I was like paying for this girl. Like I was paying a ton of rent. I was working in New York, I'm just gonna stack the money. Like, I'm just not gonna. Oh, okay. I was like, where is this going? Because I was like, paying for this school. Like, I was paying a ton of rent. I was working in New York. I was paying that rent. I said, you know what? We're doing nil on rent. I'm gonna pay like 1200.

I'm gonna live in one room. And that way, I can't even have people over. I just have one chair. Now it's a reclining chair. It's my couch, it's my chair. But it's one. It's not for company. So it's just a recliner?

It's a recliner. Okay. So I had my bed and I had a recliner. Have you seen the movie Trap? No. Josh Hartnett plays a murderer. He too had a studio with just a chair in it. Just a chair.

So think about his murders. By the way, the chair was amazing from West Elm. It looked like a nice, it wasn't Lazy Boy recliner, I elevated it. Because I said, if I'm only gonna have one chair, I don't have to spend all these furniture, I'm going to buy a nice chair. Living on top of me was this girl, Kim, who's an amazing writer, shout out to Kim. And she was living with a gay dude. We won't shout him out. Yeah, boo.

Yeah. And she was living on top of me, and we kind of became friendly. She was queer, she came out to me, she presents more feminine. So I felt like, you know, then she was a rabbi. I want you to meet my partner, and it was a dyke, and I said, I see you, Kim. And Kim is black, and Kim for Juneteenth,

which was the first, it was 2020. So we shut down. Yes. Juneteenth was a big deal in 2020. I felt like which was the first time, it was 2020. So we shut down. Yes. Juneteenth was a big deal in 2020. I felt like more was made of it because, A, it was after, you know, a lot of exposure, obviously, of the climate. But I think it was the first time it was recognized. But I could be wrong. Maybe it was a year before.

Yeah, I think that was the year they're like, it's now a federal holiday. That's what I'm saying. They were like, this is not what we asked for, but OK. So, but it was still COVID-ish. It was in the summer, so it was a few months after, and you still had to like kind of distance. And she came down to my little hovel that I called it,

as I had one little window. And you could kind of see me in it. You kind of like see me in the window, you know? And I see Kim's feet coming down, because her stairs are right there, like towards, to her car. And she's like, by the way, like, just so you know, there's going to be like a big, you know, cookout, people bringing different things, and so it's not typical.

But you're welcome to come. And I didn't really want to intrude. So then I was home. And it was like, you know, 50 black people in my front yard, which we shared as one of these houses that's broken down and I was in the hovel space. But she really insisted. Then she came to my apartment, she's this food and everything, and the food was phenomenal. And then I ended up, like before I know it, I'm, having the best time on the Juneteenth, you know, cookout and eat.

I feel that I didn't bring anything, but everybody saw how I was living. I didn't even have a real kitchen. I had a hot plate. Like, it was not a hot plate that you would bring out if I wanted to make a steak or something. You made steaks on a hot plate? Yeah. Have you ever seen the videos of a man who, um, he'll like make spaghetti in his toilet? No. It's really upsetting. That's really upsetting. This is a clean hot plate. He'll like fill a sink with water and like put a like a heater in it and like boil things in his sink. Why? I don't know. Like everything was nice in my hovel. I just want

to be very clear. It was like as if this room was your apartment. OK. Do you know what I mean? But much lower ceilings. Much lower ceilings? Were you in a basement? Yeah, it was a basement. Oh my god.

It was a basement. How long did you live there? I lived like a year and a half, two years. Well, let's start this episode. OK, great. Well, anyway, so. Wait, what did you eat at the cookout? I ate everything. Tons of meats.

Okay. And different macaroni salads. I had beers. Was there mac and cheese there? Yeah, yeah, yeah. Oh yeah. A bunch of different types of things like that, which I enjoy.

And I brought flowers was really the only thing. I didn't make anything, but, and the desserts were good and the conversation was terrific. But I haven't been back to a job, but this is all to say that it is, I'd love an invite. Okay. To the Summer Cookout, okay. I understand why it's not appropriate for me to be there.

No, no, you can come. Spaces are spaces. But now I can make something. What can you make? I'm just saying I can make something. What can you make? I can make guacamole. Okay.

Okay. I can make steak and salad. I can make crab legs. You're going to bring steak and salad to a cookout? If you want it. I'll take it. So the person you're listening to is a hilarious comedian whose name one of Vulture's comedians

you should know. This is wild. She's written for shows like The Chris Gethard Show, The Baroness Monsquette Show. And you can hear on her own podcast called Too Far. New York Times calls it addictive. Oh. Well, do a little at a time so you don't OD.

I'm thrilled she's here. It's Robbie Hoffman. I love you so much. I love you, Robbie. Thank you so much for being here. Thank you for having me. This is really, this is a big one for me. Wait, so did you date when you were younger or did you, when did you start dating? I maybe I had my first girlfriend when I was 17. Okay. Yeah, no, I didn't date. I gave hand jobs and I was very slutty in that way and like a Jewish school slutty. Because here's the thing, I was the poor kid at this great amazing school. Like that was a huge privilege that I went to this like private Jewish school that was like a million dollars a year and I went on subsidy. So that's what really highlighted

how poor I was was that there was so many rich Jews and then it started like dawning on me like how do you even get born poor and Jewish anymore? Like everything was like it felt so random. It felt so like it felt like final destination. It's like Jews haven't been that poor like poor for a while now. Like I felt like but of course the religious like, Jews haven't been that poor for a while now. I felt like, but of course the religious, it's different, but they are having all those kids. Like, it's a little bit there, for us a little bit of this, whatever.

When you're poor and you don't have the clothes and stuff, you know, I remember Free Dress Day, I was the kind of kid that said, oh, I forgot it was Free Dress Day, I wore my uniform just because I didn't have like, you know, the- You didn't have the newest, latest shit. just because I didn't have like, you know. You didn't have like the newest, latest shit. Yeah, I didn't have like Miss 60 jeans.

Like my best friend sat me down when I was like in ninth grade and she was like, you're bringing down the group, you need a pair of Miss 60s. You're bringing down the group. This is what she told me. You're bringing down the group, you need to wear a purse.

Like a bag. Like a little coach bag? Yeah, like I got one from Levi's. Okay. And it was like, you know, it was like, by the way, there were signs, it was green corduroy, but anyway. But she didn't want me to use a backpack anymore. I have to use this thing, but I'm like, but it's so heavy. Like on one shoulder, like I can't,

and she was like, I don't care what it is, you put it in there. Okay, so this happened, but then free dress day. And she was like, I don't care what it is, you put it in there. Okay, so this happened. But then Free Dress Day, so I would always come. But I did bring the topics. The topics? Like, I brought, like, the, you know, the tea,

and I was good at talking. Like, I brought, like, the hot topics. Oh, I was like, what are you talking about? So you contributed in a different way to the group. Yeah, like, my friends, like, you know, like, what are you talking about? So you contributed in a different way to the group. Yeah, like my friends like, you know, like, I remember we went out when we were like 17 or 18. Yeah, you know, they paid maybe for the cab or whatever. These people got allowance and so we got a cab.

These people. Yeah, and we went, we went, we went. These people got allowance. We went like downtown and we were at this place, this really fancy hotel where all these hockey players would go and drink on their off nights or something. We would go without, we would sneak in, we're like, can you believe they let us in? It's like, yeah, eight slutty girls, like 17.

I'm like, we got in, like as if it's a win. Like these are all pedophiles. Yeah. You know? I mean, yes, it is wild when you're like a teen and you're like, I can't believe they let me in. It's like, of course they did. Yeah, I don't remember actually our friend John,

who was like, had a car or something, came with us once and they didn't let him in, but they let all of us in. Of course. And they said it was his shoes. And I'm like, I was like, well, those shoes. And it's like, no, clearly they don't want John there. Yeah, they don't want men in there. There's enough men.

There's enough men. So, but I would be the one in the groups. I had no money for drinks, but I'm like, girls, we are drinking first round for free. I will go up to literally, and I'm telling you, these places, like Justin Trudeau was there and like hockey players. Like it was like a scene.

The creme de la creme of Canada. It really was the creme de la creme of Canada. So they had an inn, they would put us on a list, whatever, whatever. And I would go and be like, fellas, what are we drinking? I would like go to the tables that had the- At 17, you had game. Yeah, that had like the bottles, you know, the Grey Goose and the girl there all night.

Like I would be like, what are we drinking? And we'd all be sitting in your separate carafe for the orange juice. You know, like the whole scene. Yeah, what, table service? What is it called? Yeah, table service. We got a table. Yeah, yeah, table service.

And we were, oh, sure. And I'm like, oh, I have some friends. It's like, well, sure. These are 40 year old pedophiles, you know, and, and we're sitting there. So it was just, I always con- I made sure I earned my stay. I don't have any money, but I can get us drinks. I'm going to get us dick. I'm going to get us drinks. I was very fine about that. So you were a madam. Yeah. I'm like, well dick. I'm gonna get us drinks. I was very fine about that. So you were a madam.

Yeah, I was like, what do you like? I was literally like, I just didn't care. Wait, that's so wild. I really love this side of you. Thank you. And then when you were in Montreal, and you were like running around getting dick and stuff, were you on the low dating women or were you bi? Yeah, so I was, I guess, I had my first girlfriend

at like 17 or 18, I was very secret. And then I was out, and then I wanted to sleep with a guy just in case. Then I wasn't, you know, I'm like, well, this is a big decision. You know, because I thought even as a kid, like, well, if you ever want to tattoo, you wait a year. You know, these aren't willy nilly things.

Very pragmatic. I think I'm using that correctly. Thank you. And then like, you know, with my top surgery, I remember I wanted that, you know, I said, well, if I tattoo you wait a year, top surgery, we're waiting too. You know, so I make these like rules for myself, so the same with Kay, I'm like, let's hold. Hold the horses.

This is the rest of your life Rob, you're 17 years old. What do you know? You can't go back. Yeah, you're not like, you could still marry Rich, you know these guys, like you could have what you wanted, which was at the time really not to do much if I could get away with doing nothing and being rich was a real...

A nice dream. It was a very big dream. And I was getting rich boys. Oh. The boys into me were these rich Jews who were like, I was bringing all the fun convo. You know, I was hot, whatever. I got along with their parents, you know?

I was hot, whatever. No, but like literally, I was using everything. The only thing I didn't have was money, which was judged at that point. I remember this guy, Ryan, was like, he once I was close enough to him, he dropped me off at my mother's house, and he's like, this is your mother's house?

Oh my God, he said it out loud? He said it out loud. That's fucked up. He said it out loud. That's an inside thought. That's something you keep on the inside. No, but it really... But also you just don't judge somebody's house. I could feel that he, something changed in his feelings for me.

Oh. And it made me feel like I needed rich people. Like I, you know what I mean? And so we're not friends anymore, but for the longest time I thought, well, he would always say things like, who's gonna do this for you? Who's gonna do that? And then I started realizing,

well, I'm probably gonna have to do it for myself because I can't take that sort of heaviness. That's like Cher. Cher was like, I don't know, somebody said something about her marrying a rich guy and she was like, I am the rich man, mother. I think her mom asked her that. And you are your own rich man.

I am. We're getting there. We're getting there. So, yeah, so I dated and I slept with him. I decided to sleep with him, but it was... Even though he was mean to you, you're like... So this was before, I think, I started losing, like, my lustre on him. He was also really smart. Mm- smart, which I've always liked.

Like my favorite type of men are very smart men. This is, you know, so I've always, I'm like, but he's really smart. I really like, for some reason I like when a guy is really smart, which of course sounds obvious, but I don't know, and not that I find it surprising when they are, but it feels like of an older sense of a man. Like somebody who's just really smart, but they don't really have much else.

I mean, he was rich too, but it's like, I don't know. I let them get away with murder, I guess, if they're really, like I thought he was like, so anyway, so I decided one day, we should have sex. Mm-hmm. And he was like, And he was like naked three seconds later.

He's like, let's fucking do this. Yeah, and he was like really lanky, and you know, he was like 6'2 and 12 pounds, and you know, and he was like skinnier than me, and I was skinny. And the whole thing, I was like, you know what, never mind, get dressed. I regret the whole thing. And he's like, okay, he's like shuffling back, getting dressed. And then I come back later.

Wait, did you say, I regret the whole thing? Yeah, I was like, you know what, because you're standing there naked, like the lights, I'm like, there's no like... The whole thing turned me off. But then my sister was like, you just have to push through. Huh? And my sister was like But then my sister was like, you just have to push through. Huh? And my sister was like,

my older sister was like, you really just have to push through if you want to have sex. It's going to be bad for a while. We'll just do it a bunch. It's going to be bad for a while. Yeah, it'll hurt. Okay.

So anyways, so then I decided we're going to have sex. So I'm like, okay, let's really do it. So he's on top of me and two, three thrust in. I said, get off of me, get off of me. And we woke up in the morning, I said, your armpit hair, the whole thing was throwing me off. I didn't like the proximity, he's like on top of me, but the tuft of armpit hair is still to this day.

So impossible for me to get over that. I don't even remember anything else about it. And then the next morning, so I was like, I'm really unattractive to you. And then he says... He said, Rifka, which is my given name, he said, Rifka, we have an undeniable sexual chemistry. And wait, how old are you?

We're like 21 by here. Okay. We have an undeniable sexual chemistry. And you were like, I don't like this. How old are you? We're like 21 by here. Okay. We have an undeniable sexual chemistry. How am I going to do there? And you were like, I don't like this. No. I don't want this. It was maybe three pumps.

Oh boy. Undeniable sexual chemistry. And what did you say? I was just like, I'm gay. Did you come out to your mom? I did. What did she say? Did she go, I knew?

No, she was fine. I just, I was outed and I just talked about this. I won't rehash, but I was outed and then I found like, I felt like my siblings might go home. I was more outed socially first, like my, my class and stuff knew about it or people I went to school with. And so I kind of ran home. I was living on my own at the time.

I was probably 17 or 18. And I kind of went to my mom's and I was like, Ma, I have a girlfriend, she's blonde. And she was like, does she want to come for Shabbos? I'm like, nobody wants to come here. And she was very, very good. Now she's Jews for Jesus. So she's homophobic again.

But she had a good window. You know, sometimes you gotta complete a circle. Yeah, she had a good window when she wasn't. Jews for Jesus? Yeah. Well, don't Jews believe that Jesus existed? Yeah, of course. Yeshua. We just don't know... Judaism doesn't have defined, like, this is God, this isn't God, this is

nevermind a narrative, this is God's stepmother, this is his son. We think it's all possible. We don't have these defined versions. We think that they were a good people, but we don't have saints or an elevation of people or kings or things like that. We did have leaders like King David and stuff, but they were more so like community leaders or something. It doesn't, we just don't have that hierarchy of like,

sainthood or bishops or every person is, can be as special as the next person. Have you read the Torah? Yeah. Like front to back? Probably a few times. Really? Yeah.

I grew up in the church and I've never read the Bible front to back. That shit is hard. We had a class called Tanakh where we just went through it. So I think you went through it like every year in school. Oh my God. That's a lot. It was a lot. But like each chapter takes like, you know, even two lines.

You're like, well, what does this word mean? And God put this and he would have put the plural, but you'll notice he put it in the singular. And what does this word mean? And God put this and he would have put the plural, but you'll notice he put it in the singular. And what does that tell us? This was my class. That's wild. Like it would be like, and the Jew is like a diamond. It may look rough.

It may be bent out of shape. But underneath is a Nishamae's soul. And it's like, where are we going with this? You're like 14 sitting in the snack class, like, what is going on with this man? What is this? Wait, that's funny. Robbie, we have to take a break. Let's do it.

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I went out with somebody who, you know, profile alone, this is one of my first, so not an app date, but before apps, whatever. Okay. I'm probably like 20. I don't even know. So what is this like eHarmony, you're on the internet? It was like plenty of fish. Okay.

And just single profile, I get to the date, she's married. She's like, she's in a, they're like, but she's allowed to- They're open. They're open, and she's married. Is that gonna be a problem? a, they're like, but she's allowed to... They're open. And she's married. Is that going to be a problem? Like, yeah, that's going to be a problem. Yeah, because you didn't state that.

And now I've come out here, I've taken the metro, I bought you a drink. It's like, now I'm $20 in the hole, I've taken the metro here, and you're married. So yeah, it's going to be a problem because it's fucking freezing outside. And then the drink finishes and she goes, do you like to stay for another one? I'm like, no. Did you say this out loud? You're like, no, no, I simply don't want to.

I said, I don't feel there's a connection here and I will be disengaging from this date and good luck with your husband and whatever else. Yeah, I think that's something you disclose. You have to say, I'm married and we're open. Now they do say that. But it's like at the time, I hope that's not gonna be a problem. She made it seem casual, casual.

It's like, no, it's a massive problem, I'm already here. Yeah, I mean. Heads up, I'm on the subway, 40 minutes. It's minus 20 outside. I've taken cash out of the ATM for this cash only for cock the fucking bar. And now you're like, it's obscene. It is fucked up.

I'm sorry, Robbie. So yeah, so just as upfront as you can be. I think so. If you're online dating, give a profile. Give a, yeah, if you have a dog, put it in there. Why not? You don't know if the dog's gonna be, you have a cat, hold it up.

I'm just saying. You have a husband, hold him up. Hold up that husband. Anything that might affect the other person Anything that forces the other person into a new relationship. I think that's smart. It's a matter of consent. I would like to hear more about your dates. Okay, so that's that. Okay, have you ever had chuckle fuckers? Like you start doing stand-up and then women start throwing themselves at you. They're like, Oh my God, Robbie, you're so fucking funny. This, that and the other.

I want to get with you. This doesn't happen to women. I guess. This is like this happens to do comics. Yes, I know. But like every now and again, I'll meet a lady who's like, yeah, it's happened. Very few. Yeah, it barely. First of all, I don't look approachable. No, what?

I am approachable, but people, after they see me on stage, where I get out the most of my angst, I don't think I read approachable, which is very good for me. So no, I don't have that a ton. That said, it certainly helps in my love life So no, I don't have that a ton. That said, it certainly helps in my love life

to have the, you know, to have the, I hate the word chuckle, you must too. Isn't it just? Chuckle, tee hee hee, da ba ba ba ba boo chuckle. I don't mind it. But just for us to be funny, it's helpful for us. Yes. It's certainly helpful.

But you gotta use whatever you have. So yeah. I don't know. How did you meet your current partner? I met her outside. What? Just outside? No, I was catching up with a friend at the end of the night and then we went outside

to bum a cigarette and then, you know, it wasn't really anyone there. And she was standing right on the curb with a few friends. And one of the friends was looking at me like a dyke looking, you know, it was kind of a queer space and, you know, like a masculine kind of dyke was looking at me, I was like, we really should go. Yeah, because I'm not gay like that. What do you mean? Like, like, you know, dyke to dyke like like masks I'm like, I'm not I don't do the mask for a mask

You know like that's like real gay like the only thing I would make me feel gay Like I don't feel like I look like this and Gabby looks like her like basically It's a boy one kind of the girl one like the boy one and the girl one. Yeah, it kind of we live a very Almost a heteronormative lifestyle. Okay. Okay, like, basically, the only gay thing about me is that I'm gay, but other than that, I'm not even gay.

The only gay thing about me is I fuck women and I'm a woman. Yeah, the only thing that would make me feel gay is when like, I'm asked like this, like a dyke, another like, butchie lesbian, kind of, I'm like, what am I fucking gay? Like, I'm just like, what are you doing? But that's, you know, that exists in the scene and I wish him well.

You know, the real gays, I consider you guys the real gays. So she was coming up to me, I'm like, oh no. But, miracle sent by God above. This dyke recognized me for my stand-up, which was starting to happen a little bit, but never in opportune times. It happens when I'm like, alone on the street outside the CVS,

it's like nobody saw this. This is going nowhere. It's not helpful. Okay? But I get spotted. Oh, I'm just a big fan of your stand up. With an ear shot of Gabby. At this point, I've clocked and looked at.

Yes. And I'm... You're into. I'm into. I'm like, one of these things doesn't belong here. We're at this like queer dyke bar. I'm like... So I'm like, forget you.

I'm like, thank you so much. You know, I'm elevating the sound So I'm like, forget you. I'm like, thank you so much. And, you know, I'm elevating the power, making it as loud as possible. Yes. Yeah, drawing attention to yourself. Oh, I was out. Keep talking a little. Yeah, which joke in particular, just resonated.

What specific joke is your favorite? Yeah. And so I go, well, nevermind you, who's that? And they go, oh, it's a bachelor. Never mind you. I was like, the bachelor's gay? Uh-huh. And they were like, no, whatever, she's exploring.

And I was like, well, how old are you? And she was like 32, and I'm like, exploring. What are you, Dora the Explorer? What are you, 16? It's over, you're 32. It's over. So then I just, you know, I said, I don't want to mince words. I don't want to, you know, I know you're leaving there. Uber was coming or whatever.

I was like, I got to get your number and take you out. I'll be back next week. And yeah, I'd be remiss if I didn't ask you out. And we had a very good banter. And her friend was like, and the you out. And we had a very good banter. And her friend was like, and the first question, so I sat exploring and then she was like, yeah, I'm kind of exploring. She's like in these Daisy Dukes and whatever.

And I'm like, and then I was like, do you come for money? And then that's my second question because I really have considered after dating, my advice to people is like date within your class. Not current class necessarily, but how you grew up. Like to me, that's like dating outside of the faith. Okay. Like it's like how you grew up,

because money is such the current religion or the current unfortunate reality of the world that we're living in, it permeates every facet of your life. So it's one of those things that is like religion, that is like if somebody wakes up and prays, or it's so fundamental to all of your interactions and transactions and everything. So when I dated like rich girls in the past,

there's always been kind of a hiccup, even if I've had more money than them in the current. But because they grew up with money, there's a different lifestyle. Just an inherent different way of acting. Yeah, like sometimes, you know, okay, I don't wanna spend 7.99 on raspberries. I understand I have the money in the account,

but that is a price that is too far for me at this current. That is not something I'm not there yet. Okay. Okay, it doesn't mean just because the money's there. I don't find that value. It doesn't mean I won't spend. But hiccups like that are kind of with you throughout your life of whatever. You know, we all have different relationships to money.

So she thankfully was like, well, I don't know. I grew up on the military. I'm like, say no more. And I was like, I really, you know, I'd be remiss if I didn't ask you. And then her friend was like, I'll give you her number. Cause her friend was a fan of mine, friends with her. And I said, I'm not taking nothing from you. I'm getting it from the source.

I'm testing the number right now. So I text her, Robbie, huh? Uh-huh. She gets it. I go, well, the response would be nice. And she hits me with the Gabby. Uh-huh. And then I...

I was back, uh, I was, uh, it's funny, I was, uh, with Adam Friedland. I was like low on, I was feeling like low on money or something that, that month. It was like, I wasn't, I was like, Adam, can I open for you on tour? Or whatever. It's like, I'm going to night. Which dates? I'm like, will you pay for my room? Uh-huh. Will you fly me out? Yeah.

Can I have an Uber? And he did. And, but the whole time, I was like, it'll be fun, we'll hang out. And I'm like, with a mask? Why are you wearing this mask? Why won't you hang out? He's like, why can't we watch a movie? I'm like, I can't hang out with you.

Holy, because I didn't want to get COVID. Yes, because you had a mission. You had to get back home and go out with Gabby. Yeah, there was a big COVID. Yeah, because I had to go home. And he's like, what did you book? She books. Robbie often books.

I'm like, this is better than any booking you could think of. Uh-huh. And I took her out. I got the car detailed, cleaned, and I picked her up. Is this your current car or your old car? This is my current car, which is also an old car from 2007. It's still a Porsche. It is. That's what I tell people.

You can judge my Porsche. It's a Porsche. It's a Porsche. All right. $13,000 and it's a fun car. And I don't have a car payment. You guys are leasing your 30K Kia's for $350 a month. It's ridiculous. I'm passing you on the freeway, no problem. They got $350 a month on this Kia.

It just, it doesn't get any better. Where did you go on your first date? We went to a restaurant called Mother Wolf, which... I like it. You don't like it? What did you get? Have you had the brandzino? It was a Monday night. Okay. There's nothing really on Monday night.

A lot of cuisine that I like. A lot of Asian is closed. So I couldn't bring her to, okay, Takes, the French restaurant near me, it's closed. There's a lot closed on Monday. So I wasn't really in my spaces. Like I like to like know the restaurant, you know?

And there's only a couple that I have that I'm like comfortable. So this is like my friend, oh, my friend, this is my friend Kathleen. Shout out to Kathleen Monroe, who's the lead of Law and Order Toronto now, booked a huge gig and just killing it in the face of Canada, really.

But she's, I called her to make my reservation because I said, don't let, I never get good with these reservations on the call. You know, and I want a good table. I said, the corner table is something. And whenever I asked, they're like, well, we can't make any promises. Like, just promise me. Just, oh,, I said why can't you make promise Monday? What do you do?

like so Kathleen called and I was like so she's like I have her as I'm like, but you have to make sure it's under my name It can't be under Kathleen. There's no way I can show up and the rezo is under Kathleen. There's no explaining that. You could just be like, my friend made the reservation. You can't to a girl. Or my assistant made the reservation. No, she would say, who's Kathleen? Oh, I see.

To a girl, they don't like any other girl name. If I said Michael, if I said anything, it would be fine. Oh, it's a two for Kathleen. It's not good. You don't want to start on a hiccup. Make things as smooth as possible. Make sure you have a good reservation. Wash the car.

Pick up. And that's it, you know? Wait, that's wild that you picked her up on the first date. I don't let people pick me up. Well, maybe for the right guy you would. You gotta meet at the location so then I have an out because I feel like if you brought me, you have to take me. Yeah.

And then I feel like it's rude if you brought me and then I decide to be taken by an Uber or something. Sure, but you're allowed to be rude. Hmm. That is nice, Robbie. How was dinner? What did you get? It was excellent.

So the food was good. I do think it's very overpriced. I really, really do. I really don't think a wine, a glass of wine should be the cost of a bottle. I don't care what restaurant. I don't think it should be $18. I just, it's just, it's not even a thing.

It's just, you guys, you know, it's egregious. Well, they have to pay for rent and stuff and they have to pay for the staff. Yeah, but we're paying the staff because we're paying the tip and the extra service fee for the staff that the restaurant is not paying for the staff. They're putting it on us.

If they did tell me that they were paying the staff that the restaurant is not paying for the staff. They're putting it on us. If they did tell me that they were paying the staff and we didn't have another 5% service charge there for the staff, and they tell you it's so they can have proper wages, you do that! You do that! I just paid $18! It is wild that servers get paid like $2 an hour. Exactly. They should have minimum wage plus tips.

They should. Yeah. Or more than minimum wage. Exactly. So we can eliminate tipping. Yeah. Did you know that stems from racism? I do.

Isn't that wild? Yeah. No. I got a lot of flack for this, but it absolutely stems from racism because people would take the, you know, people of color. Who gave you flack? Oh my God. I went viral with this. No tipping.

That we should stop tipping and start paying people a living wage, leave us alone already. We should hold employers' feet to the fire and they should be, if you can't afford to pay employees for your business, you can't afford to open your business. And wait, people got mad at you about this? People were like, well, we're not going to have... I was like, no, we should not be levying wages onto the consumer because it continues to perpetuate a system where the poor are turned on the poor.

The poor are supporting the poor. And it's really time to... Yeah, the model has gotten out of control. It stems from racism and sexism. Typically... Servers are women. Servers were women and black women. And it's archaic. Yeah, I think we should do away tipping.

We don't have to tip in Europe. No. Because they get a living wage, and that's nice. And it's like the same thing when like, whenever I see people be like, oh, airplane seats should be bigger. And people are like, no, you should just lose weight. And I'm like, but you would be more comfortable in a bigger seat.

No, exactly. And I'm small and they're too small. Yes! They're too small. They're too tiny. They're too small. It shouldn't fit me exact. No, you're very small. I'm very small. If something fits me exact, that's for children. It's for children. It is for children. When I was on this kid's job, I worked on Odd Squad for three and a half years, which

is a PBS show. We had the kid actors. They were like 13, 14 years old. I was the same size 13, 14 year old boy. So sometimes I would be a stand-in and I'm like, the stand-in's not here, Robbie. That is a child. We'll be right back after this quick break. You ever catch yourself thinking about food way too much?

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visit equip.health slash date me. That's equip.health slash date me. Calling all listeners, we're conducting an audience survey at gum.fm slash date me. And we wanna hear from you so we can keep making content you love. conducting an audience survey at gum.fm slash date me. And we want to hear from you so we can keep making content you love. You know this. Oh, we know this.

There are ads on my podcast. We want to improve that experience. But in order to do this, we need to know a little bit more about you, our audience. This survey is quick, it's easy, and a free way to support this podcast. It'll take you two minutes and you'll be helping us out so much by doing it. Go to gum.fm slash date me to fill out our survey. That's gum, g-u-m dot fm slash date me. So okay, you go on this first date to Mother Wolf, you have a delicious expensive dinner. Did you drop her off? Did you go to a second location?

Yeah, so then I did that thing that I either saw it in Harry Met Sally or Annie Hall. One of these like early rom-coms where it was like, you get the kiss out of the way. Oh. Right. So I was like, I went to the bathroom and I always remember that. Like, I must have watched it when I was like, also like 15, 16. like 15, 16. You got the kiss out of the way. Okay. So I went to the bathroom. I paid. Here's another tip. If you're planning to pay, typically you have to pee or go to the bathroom right after the meal, but you know, let them bring the bill first. You don't want to leave your date with the bill sitting on the thing

and she felt like she had. So I don't care how badly I have to pee. Just typically by then you've had a glass of wine, some water, lots of food. You got to pee. I wait, I put the check, I put the card, then I go pee. That's what I do. So that's just an order. The order of events that need to happen. Yeah, because, that.

Okay. Yeah, because then it looks, it just looks bad if you come back and the bill's already there and you've, and she was like, no, no, and then sometimes I really enjoy the person. I did this on the second date on the way to the bathroom. I give the card, please cover this. And then that's very exciting. Oh, you did it. Oh my God.

How fancy. It'll make you feel good. It makes them feel good. Everybody's happy. And so I go to the bathroom, I come back, I said, okay, I paid up, we're good. What we're gonna do is we're gonna go in the car. We're gonna kiss in the car.

You said this out loud. Yeah, I said, what we're gonna do is we're gonna get in the car. I said, we're gonna find a great song. We're gonna kiss in the car. I have, we're going to find a great song. Okay. We're going to kiss in the car. I have a ciggy. We'll share a ciggy.

We'll share a ciggy. We'll sit in the car. If we like kissing, we can continue to kiss in the car. I can bring you home. We can kiss there. I can drop you off. We can kiss. We just, let's take a minute.

We don't even, let's, we're going to get in the car. We're going to get our jackets. We're going to find a song. And then I was taking, so then we get into the car. I was finding forever to find a song. And she didn't like my song. She's much better at music than me. You know, I got Lincoln.

What song did you pick? I got like Lincoln Park. And I got like. No! I got like. No! Yeah, yeah, I have like whatever music I have. I don't know what I have.

I have like 40 songs. Okay. I don't know what I have. I have like 40 songs. Okay. You don't have like Apple Music, where you have like all the songs? I have Amazon Music, which nobody but me has. But I have it because my friend works at Amazon and gave me the sign in. But they're still in beta, I think.

So they don't have all the tunes. You know, it's not like they have the newest Billie Eilish. They're not up to speed over there. They have Linkin Park. So anyway, so then I finally find a song. I don't even remember the song, but she was like, you have to kiss me already. By the time.

Kiss, it was amazing. We ended up going back to her house. We're kissing, making out, the whole thing. That's really sweet. Yeah. And then I left 11 o'clock. Okay. I'm not overstaying. First of all, I've had a glass of wine. I'm not going to stay for another one. I'm driving.

And then I go, you know what? It's 11 o'clock. I'm going. I'm taking it. We will plan the next date. It'll be after tomorrow. It won't be tomorrow. It'll be after tomorrow. Why did it have to be after tomorrow? He needed to digest, but I didn't want her to think, oh, we're not waiting weeks either.

Okay. We have a connection, let's go. Mm-hmm. And how long has it been? It's been a year and a half, over a year and a half. That's sweet. Yeah. That's so sweet. Yeah, and we still, like, I love dating.

We just went to Little Dom's yesterday. What'd you get? We got the white pasta with the peas and the cream. Ooh, yeah, yeah, yeah. What's it called? It's um, parpe de la? Yes! I think.

That's exactly it. We got the rice balls. The sausage, ugh, I like the rice balls. We got the carpaccio, the meat, the raw meat. I fuck with the raw meat. And we got like the raw meat. Like, fuck with the raw meat. And we got, uh, like the gem salad. If you go on Fridays, they have lasagna. Yeah, well...

But you gotta go early, because they sell out. Ugh. It's the stress of these restaurants, guys. You can't be selling out of your product. I mean, this is... Does Apple run out of iPhones? I mean, what's going on? They do.

Oh, they do? Yeah, I bought an iPhone once, and they didn't have the color I mean, what's going on? They do. Oh, they do? Yeah, I bought an iPhone once and they didn't have the color I wanted and I had to go back. What color did you want? I wanted pink. What, what?

There's a case on it. You can't even like see it. Well, now this is a white one because they didn't have. Well, I thought I bought a black phone and look, it's basically blue. Oh, I don't know where it is. Oh, it's here.

Isn't this blue? That is blue. Why don't you have a case on that? I don't fuck with a case. Why? I live life on the edge. But what if you drop it in and crack it? Is what it is.

You'll just have a cracked fucking phone? No, the thing is, is you get comfortable holding it. Like, first of all, I've dropped it so many times that I feel like it's hardened it in more. That's not, no, no, no, no, no, no, no, no, no that I feel like it's hardened it in more. That's not, no, no, no, no, no, no, no. I do think it's upholding his legacy. I am. I think he would roll over. If after he died, you know the first product they put out was this Apple watch,

which is basically an iPhone 3G on a strap. Square and everything, he would roll over. You don't think he had any involvement in that? Yes, he would have waited 20 years, whatever it took, until it looked like this. If it didn't look like a regular watch, remember how we, and I've talked about this, but it's so important for people who are innovating and doing this.

Remember when he- People who aren't innovating. All people who work in tech. You're out there in tech, listen the fuck up. State of the art, that's technology and art. Marry them. Okay? He brought out the Apple MacBook Air in a manila envelope, regular envelope. He's like, oh, the mail came in. He comes out there. He goes, I wonder what's in this envelope? Takes out, put it in his paper, goes, we will. It was like, okay, he would have done this shit with this.

Let's say the watch was ready. He wouldn't have rushed it. He would have been like strapping on his watch, buckling it on, he would have been like, it's alive. It would have been like, it just, it would have been like him getting dressed, like putting on his watch, and it would have looked like a watch. Thin and like regular watch after like,

it wouldn't be like the TV that is it art. Like, no, you would have thought it was a watch. And it's still a square. Can you imagine that iPhone is, or Apple is still putting out the Apple Watch and it's a bubbly square, a watch. There's never been a watch shape like that. There's been the square, there's been the tank,

there's been the Cartier. Not the rounded edge square. It looks like no other watch, Because it is not a watch. It is a mini iPhone. On a fucking strap that nobody cares you could swap out. I tried to wear one for the longest time. I don't, I didn't like it. No.

It doesn't look right. No. I even put like a little, like a chain-y kind of band on it. It just didn't look right. It does not look right because it isn't right. If it doesn't look right, if it doesn't smell right, something's off. Something's off. It should just be a watch.

We're still not as like, we never think somebody's wearing a watch. We think they're wearing an Apple watch, which is not a watch. It's not a watch. Uh, it... So he... It saddens me that he would, you know, he would see such a product with his, you know... There's no way he would have put that out. But anyway... Robbie?

Sombra note to end on, but... No. No, we're gonna bring it back up. Do you have any advice for single people? I do. Okay. This is actually... I think we've overcomplicated dating. There's so many options, there's so many things, and there's a simple equation that we're forgetting.

And it applies to everyone. Okay. And this is a new theory that I've developed, so it's, you know... Bear with me. How new? This is a new theory that I've developed. So it's, you know, bear with me. How new? This is the first time I'm telling you. Ooh. Okay. I think per every relationship, per every relationship,

you need one hot person. Okay. One smart. How you divvy it up, I don't give a fuck. Okay. It's a simple equation. One hot, one smart, how you divvy it. You need a hundred and both though.

You need a hundred, okay. The classic example, we see this, okay. Typically you see the older, the older smart guy, the older smart gentleman, you know, with like a young hot thing. Beautiful, it's a classic, we love it. That's like slipping into a pair of Calvin's, okay? Americans are never gonna get over that duo.

It's here to stay. It's here to stay. But you ever see like an Abercrombie pretty boy type with like a bookish, you know, maybe glasses wearing girl? Not really. A Walk to Remember? Was that a fucking movie? It was. That shit works too.

Okay. We don't see this much, but it works. Okay. This shit works. This shit works. Right? One hot, one smart. How you, who picks what?

I don't give a shit. Even in my relationship, people think in my relationship, Gabby's 100% the smart circle, right? And I'm, no, the Gabby's 100%, the hot circle, I'm 100% the smart circle. No, no, no. Right? People assume Gabby, Gabby's the hot, right? Now I happen to be a little bit of a cutie.

Yes. So I give myself 10% in that circle. I'm contributing. Yes. I'm giving her 90 still. There's no question she's got 90 there. But I've topped us off. I've topped us off.

So we have 100 in that. Now on the smart circle, people assume, it's me, no, no, no. Gabby was an ICU nurse for eight years, basically a fucking doctor through COVID. We share the smarts 50-50. It is one hot, one smart, how you divvy that, I don't care, right? Too hot.

I get it. Let's say, as an example, you're looking, you're into looks only, you're swiping hot. Too hot. It can never work. Look at Hollywood, it's a disaster. J.Lo and Ben, how many times are they going to try before they realize? It's not going to happen. They're missing a whole fucking circle.

J.Lo and Ben can never be. They're missing a circle. So who do you think J-Hope should be with? She needs smart. You don't think Ben Affleck's smart? I think together they're both leading with hot. Okay. So they probably, the circle is too much. They probably have 150, and they're in a deficit on the smart circle.

Okay. Is there not idiots? No. Okay, but something's not working. And it's time to take a hard look. Okay, but sometimes you have two smarts, that's two uggos. You don't want that either, you gotta be careful. That's why you need the hot too. Like it's it is as important. Both are as important.

But some people are only swiping hot when they might have some hots and I'm like, but you're bringing 70% hot. Why are you looking at a hundred percent hot? Your smart circle's at 30% Not a hundred percent hot. Your smart circles at 30 percent. I think you actually might be on to something. You just need two. One smart, one hot. How you divvy it, I don't care. Just get to that number. Hundred in both. I think that's good advice, Ron. You'll see hot girls looking for hot guys, and you'll see hot guys looking for hot girls.

And I'm like, what? We're missing circles. We're missing the smart circle. And sometimes you see smart people going for smart, and they're wondering why they need to be hung from a tree. They're doing all the weird kink, whatever. It's like, something's going on, guys. But maybe some...

They're overthinking it, because they don't have the natural hots. They're not coming with the natural hot. They have to overthink it with swings and everything else. But maybe some people like swings, Robbie. That's also true. That's also true. That's also true.

It doesn't mean if you're hot, you can't do it. I'm just saying you'll notice that more of that stuff happens in those circles because they're overthinking it because they have to bring out, it's like somebody naturally, right? We have to know what we are. Like if you, you know, I know I'm probably at a 30, 70. What's your circle?

Where are you standing with hot and smart? What do you need? If you're a girl and you're bringing both, you have 50% you're hot, 50% you're smart. We need that match. I think I might be 50, 50. That's important. Or maybe I'm like 60-40. I think I'm 60 hot, 40 smart.

Well, here's why we give you 50-50, because comedy is so brilliant. Okay, I'm 50-50. Here's the thing with comedy. Comedy takes sarcasm. Anything with like a nuance or a deeper level or a double on tone or double meaning, I find is like inherently smart.

So comedy's a fun one because, yeah, I think comedians immediately, if they're doing well, they contribute a little bit more sometimes on the smart. Okay. And so we don't need to do as much as the other. Now, do not come to me and you're not doing nothing else. If you, you know what I mean? So if you need to be lifting at the smarts department, you gotta get, you know, if you're not bringing the smarts, definitely bring the six pack.

Definitely. Please, sir. I see these girls with these guys. I'm like, why is you're bringing everything? He's brought you nothing. I really do think you're on to something. It's a simple equation. One hot, one smart. How you divvy it up, I don't give a fuck. Robbie, I ask all my guests this. Is there anything you want to promote?

Yes, the Too Far Pod, which we are finally recording. I mean, by the time it's February, who knows? Maybe it blew up. We don't know if it's combusted, if I'm Patreon only, or where the hell I am. But Too Far Pod, New York Times calls, addictive, we'll be back. I'm also going to be on TV screens by this point. So maybe you'll know me a little bit more. Maybe you won't like me as much, maybe you will.

Okay, my acting, give it a chance. It's like stand-up. I've been Okay, my acting, give it a chance. It's like standup. I've been doing it for acting, I'm really getting better at. And you're gonna see with every project. Oh yeah, she really is. And then for nudes or anything else,

you can follow me on Instagram. What's the show? That Robbie Hoffman. Just a couple of projects. I wanna know. I'll tell you in private. Isn't that cool to say? I can't talk about it here. Would you date me? I'll tell you in private. Okay. Isn't that cool to say? I can't talk about it here.

Would you date me? I would date you in a heartbeat. Robbie, thank you. Yeah, who are you dating now? Do you talk about that on the podcast? I have. I am dating someone right now and they're very sweet. Is it they them?

No. No. Why'd you say they're very sweet? I don't know. Because you can. He's a he. Okay, there we go. We like to know when he's back and you know, he's a he.

He's a he. He's a he. He's a he. He's a he. He's a he. He's a he. Why'd you say they're very sweet? I don't know. Because you can. He's a he. Okay, there we go. We like to know what he's backin', you know what I mean? Tell me when to stop. Wow. Where'd you start?

No, I can't do that. If you like this episode of Why Won't You Date Me, you can like it, you can rate it, you can subscribe, you can give me five stars on Apple Podcasts. And if you write me something nasty hitting on me to whywon'tudatemepodcasts at gmail.com, I will read it. We are running low, so please submit them. This is from the heart. Nicole made nachos, her favorite treat,

with loads of cum instead of cheese, piled high and complete. She sprinkled it thick, so melty and yum. Nicole was soon covered in mountains of cum. With each chip she dipped, the cum stretched wide. Why are they doing that? Because I asked for it. Why, Jesus?

Because I like to be hit on. Stringy and gooey on every side. So if you see Nicole looking cummy and bright, she's been snacking on cum nachos all through the night. This is a poem. The cum came from me, didn't you see? Nicole loves cum, yes siree, love Carson. Thank you, Carson.

Thank you, Rob. Thank you, Carson. Thanks, Nicole. You know I fucking love you. And if I ever got invited to your house, I'd bring flowers, a plant, or steak and salad. Whatever you want. I want steak and salad.

Okay, I'll do it. You can talk to Tola. You know Seth Tola? Yes. When I make our steak frite with a salad, it's the one meal I make. It's excellent. Montreal steak spice. Steak spice? Yeah, Montreal is very known for their steak.

Oh. Well, I guess a lot of places are. We need to calm down. I didn't know that I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know.

I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know.

I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know. I don't know why. Bye! You've been listening to Why Won't You Date Me with me, Nicole Byer. This show is produced and edited by Mars, with executive producer Anya Kenovskaya.

It's engineered by Casey Donahue, with guest research by Lindsay Kempf. Our VP of content at Headgum is Katie Moose, and our theme music is arranged by Mike Cometay. Ah, thanks for listening. We'll be back next week with a brand new episode. See you then. Okay, bye bye.

That was a Headgum podcast. Hi, I'm Caleb Herron, host of the So True podcast, now on HeadGum. Every week me and my guests get into it and we get down to what's really going on. I ask them what's so true to them, how they got to where they are in life, a bunch of other questions, and we also may or may not test their general trivia knowledge. Whether it's one of my sworn enemies like Brittany Broski or Drew Fualow, or my actual biological mother, Kelly, my guests and I are just after the truth.

And if we find it great, and if not, no worries. So subscribe to So True on Spotify, Apple Podcasts, Pocket Casts, or wherever you get your podcasts and watch video episodes on the So True with Caleb Heron YouTube channel. New episodes drop every Thursday. Love ya!