We're Here to Help - 252: Little Boy Hands & My Dirtbag Wife (with Kal Penn)

Episode Date: January 21, 2026

The guys are joined by Guest Helper Kal Penn! Together, they help a lawyer whose colleague's tie is too short. Then, a Chicago caller thinks his wife lost a precious gift.Listen to Kal's podcast “Here We Go Again” -- distributed by iHeartPodcasts and available on the iHeartRadio app and everywhere podcasts are available now.Want to call in? Email your question to [e-mail]: https://patreon.com/heretohelppodMERCH: heretohelppod.comINSTAGRAM: @HereToHelpPodIf you’re enjoying the show, make sure to rate We’re Here to Help 5-Stars on Apple Podcasts.Advertise on We’re Here to Help via Gumball.fmSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

New Year, same extra value meals at McDonald's. So now get two snack wraps, plus fries and a medium soft drink for just $8. For limited time only, prices and participation may vary. Prices may be higher in Hawaii, Alaska, and California, and for delivery. This is a headgum podcast. And we are back. We got a guest today. The great Cal Penn is joining us.

Hey, thanks for having me, guys. Thank you, Cal. show, man. You know, Cal, you've had a really interesting career, man. Gareth and I both did Harold and Kumar together. Yep. We were all in that guy together. You popped big on that. And then you got into politics. Briefly, yes, for like two years. But you didn't go casually. I remember being like, because I've always known you as an actor, you know, I've known of you. I've been a fan for a long time, so I was always watching your work. Then you were like hanging out with Obama.

It was, yeah, I mean, I think if the only thing, I have to explain this to audiences sometimes, like if the only thing you know about me is that I played a stoner three times, and then you're like, this guy, what business does he have working for any president of the United States? Like, forget politics, just the act of doing that. And my response is always like, well, that's the American dream, baby. But also, from the outside, you did do the American dream. Also, in the second Harold and Kumar, it's loosely around the government. So maybe that was where you got the bit by the butt.

Maybe. I mean, I had no intention of actually going and working in government. It was a very different time. It was like 2007, 2008, and we were all on strike because the screenwriters were on strike. Right. And I remember Olivia Wilde, who is a wonderful actor-director. Of course, yeah. Invited me.

She was like, there's an Obama event. And at that point, he was like a junior senator from Illinois. Nobody knew how to pronounce his name. There were 12 people running for president. She's like, do you want to come to this event? I was like, absolutely not. There's nothing I would rather do less than go to a political event in Los Angeles. And the third time she asked me, she like casually was like, I mean, it's an open bar.

I was like, oh, I'm there. That's great. You should have led with free drinks. Changes everything. Totally changes everything. And then kind of one thing led to another. I ended up volunteering for the Obama campaign for a while. And then that turned into like a year and a half of kind of working on things like arts policy

and I was going to grad school at the time for international security, which is not a thing that I had, like, advertised publicly. You had been a working actor and then decided in between gigs to go back to grad school? Yeah, there was a program that you could do, like, half of it as a distant student online. Cool. So I would do it, like, you know, if I was working on a season of house, for example, I would do it during hiatus. Or I would, you know, between movies, you'd have, like, I mean, you know this.

Actors are, to me, it's like, going to grad school is the equal. equivalent of like, like, you know, like when you see actors who come into work hungover, and my first reaction is, bro, are you working so consistently throughout the year that you had to get drunk last night? By the way, you're 100% right. Like, I'm envious of that. I've never had that type of career regularity, right? You worked 14 days in 2024.

You did not need to get drunk last night. I can get drunk most Tuesdays. Yes. You have the time. I do. And then what was the Harold and Kumar experience? Because that movie really, I don't think people nowadays realize how big that movie was when it came out. Yeah.

And how nowadays everything does feel different. I say that as an old white guy. But you just see so many different people of color and everything on screen. And now with streaming, it's not odd to me to be like, oh, I'm now watching a show with people in the main cast that never would have been. It was wild when you two guys were the leads. of a studio comedy, and I was like, and that crushed, and that nobody was talking about the fact

that it was you two guys, they were just like, oh, yeah, that funny stoner movie. Totally. That's what felt good about it. I remember when we made it, you know, I couldn't believe they were making a movie like that.

In fact, John Hurwitz, who's one of the writers and creators of Harold and Kumar, I ran into him at a mutual friend's party before he had cast, before he'd sold the movie, and he sent me a script, and I was like,

this is the funniest thing I've ever read. You're never going to sell it in Hollywood, because that was my experience up until that time, right? Like, no shade to Van Wilder. I had a great time working on it, but I'm literally playing a guy named Taj Mahal. Like, he's named after a building. Wow.

That is an era. It's not even named after a person. So, again, not complaining about it, just let's set the tone of the time period. Let's live in reality. Wow. Right, no, that was the reality. So I said to her, it's like,

that there's no way you're selling a movie where these two guys are just dudes. Agreed. Like, I've been playing buildings. It's not going to happen. Like, granted, it was one of the seven wonders of the world, but it's still a building, right? So, and then he, of course, sells it. And Hurwitz says to me, I'm sorry, that was your experience, but we are making Harold and

Camar go to White Castle. We're not making a movie called David and Jason go to McDonald's. Yeah. So I was like, oh, I like this line. I like this guy. But when it came out, dude, the, you know, there was buzz during the casting process that said, we don't know if Hollywood's ready for a movie with two guys who look like me and John Cho

and my takeaway from that was you guys are underestimating the audience. You're assuming that white audiences can't laugh if somebody doesn't look like them, which is like so demeaning, frankly, and degrading to an audience, right? And I was like, that's bullshit. I love comedy, everybody loves comedy.

The movie comes out, and it does really poorly in the box office. So those first two weeks, it tanked. And so I was getting phone calls that were like, see, we told us. you. America's not ready. And you're trying to spin it.

You're like, I've always been saying that. 100%. Yeah. I was like, I was like, I'm like, that's why I'm doing Van Wilder too, you guys. I'm reading right now for Taj Mahal Senior and I'm excited about it. Yeah. But to your point, guys, the movie drops with no marketing on DVD. And fans found it on their own.

It explodes. And it explodes in Arkansas and Nebraska and Tennessee, not just the coasts. And it was so reassuring where I was like, number one, I'm very glad just selfishly that people are enjoying this movie. And number two, like, screw you old guys who underestimate the audience. Like, people just want to laugh, you know. And weed. Yeah. I will say.

Yeah. I will say, yes, you can't undermine the weed. Weed helps a lot. Yeah, but I will say in terms of that and in truth and one of the things, and I want to talk to you about your podcast, too, the why I'm loving this space. Yeah. is similar to that and how you couldn't do it in the theaters because all that shit is marketing machines. And you can feel what movies these studios want to win awards

and the agenda that Hollywood wants and what they want to win. And you know they're going to put enough money in that it's going to happen. But what I love about what DVDs did, what rentals first did, what cable did, and now what podcasts are doing is it's a democracy. Totally.

Yeah. If the audience likes something, therefore it wins. It is not about marketing. It is not about PR. It is not about a push. It's not the big studio machine goes, we're going to make a star of this kid.

Yeah. It's the audience goes, that shit was funny with those two guys in the White Castle. Why? I don't know, but I liked it. Totally. And you're like, that's all it takes. It's all it takes.

And I love that not everything has to be for everybody anymore. I agree. It's so good. I love stand-up comedy broadly. But, like, I can love a Shane Gillis, and I can love a Nanette, like the same night, and they couldn't be more different, right? And I love that about the fact that...

Man, I could not agree more. And I also, I love in doing it that now even the executives are getting it and they're giving a different style of note where they'll go like, you guys know what you're doing. And you're like, you didn't say that before you asked all. I was like, I'm glad you are now.

So I just, you and Ed Helms are doing a pod, yeah? We are. So I'm doing two right now. There's one with Ed. They're both with Ed's company, Snafu. The one I'm doing with Ed is about audiobooks. So it's a short, like six episodes for the season. And it's, I didn't realize how huge the audible audiobook space is and how people will not just listen to audiobooks, but then want to listen to podcasts that, like, dissect the audiobook. So it's massive.

It's massive. And it's so, it's like the nerdy side of me that I just think it's so interesting. Like we had, there's a book. about Mark Ronson, that was one of the ones we covered. And I got to talk to Questlove for like an hour and a half. That's cool. Just about, like, music and marketing and that whole life and that whole world. That's cool.

And then the bigger one I'm doing, it's called Here We Go Again. And it's basically a look at pop culture, history, and things that happen in politics, although it's not a political podcast, with the past, present, and future. And basically what I wanted to do with that is, like, every time I was scrolling through things. Everything is like, doom generation, the world sucks. Why would you pay attention? It's just everything's negative. And I felt like I don't have those touch points anymore of learning from somebody who is maybe a little bit older than me or more experienced or an expert in something. I was like, hey, here's how something was 50 years ago and here's where I actually think it's going

outside of this crazy next 12 hours where everyone's going psycho over a new story. So for example, we had like the first episode was Bill Nye. Everybody loves Bill Nye. And I basically get to talk to Bill Nye about the space race. And in the 1980s, the space race, I'm a big astronomy nerd. The space race was between the U.S. and the Soviet Union because of the Cold War. And now the space race is between like five billionaires basically. Yeah. Right. So like what changed? When did we go from it being publicly funded to like private sector push? Some of that, by the way, NASA was, it was like by design where they wanted to spend stuff off to be privately viable. So like just super interesting things that I didn't know.

I'll give you an example of one of the political ones. I had Pete Buttigieg, former transportation secretary, was on. And I did not want to talk to him about politics because there are great political podcasts out there. And I'm just not the yelling and screaming guy at all. I would rather make dick jokes with a political person. So I was like, okay, so I have the former transportation secretary on. I'll ask him serious things about infrastructure that sound boring when you use words like

infrastructure. But really, like my pet peeve is on the rare occasion that you're. plane lands early, how come the captain is like, well, folks, we're a half hour early. And unfortunately, there's no gate ready for us because they didn't know we were coming. So we're just going to hang. Of course they knew you were coming. That's literally how the technology works. It's crazy.

It's how it worked. That's the one thing they knew is exactly where you were and precisely what time you were coming. You can make up any excuse. But like why is that what they think were stupid enough to believe? And so, you know, Buttigieg was like, is that really the question? I was like, yes, dude. I need to know the answer. Is there an answer?

He's like, well, it's true. Podcasts are stupid. Yeah. He did answer the question. What do you say? Apparently it has to do with scheduling and the types of gates there are. So like usually there are, let's say an airport has 50 gates, but they're only using 25 of them. There are 25 ramp operations.

who know how to use the gate, and those specific gates are built to accommodate specific types of aircraft. So they knew you were coming early. They just didn't want to pay another person. Right. To get you. That's beautiful. By the way, of course.

But I also don't want to hear the pilots say that. I don't want them to go, please, everybody hang out. We wanted to save a little bit of money, so just stay in your seats. Oh, that's a good point. How enraged would be? Wait, Natalie, are they here? Yeah. Okay, Cal, so what is the name of the, uh,

new podcast. Thank you. The podcast is called Here We Go Again. It's light, funny. Hopefully you end each episode feeling a little bit better about the world and you can listen wherever you get your podcasts. I love it, brother. Thank you for joining the show. Let's take some calls. This episode of We're Here Help is brought to you by Walden University. For over 50 years, Walden University has helped working adults turn ambition into action through flexible distance learning. Today our mission is simple. Provide access to education. for professionals ready to level up and create real change. You know, Jake, you and I are big believers in evolving, always getting better, always improving.

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returns now available in Canada too. That's Q-U-I-N-C-E dot com slash here-to-help. Free shipping and 365-day returns, quince.com slash here-to-help. Hello. Hi. Hi, welcome to the show. Can we get your name, please?

Yes, my name. You can call me Sarah. All right, hi, Sarah. Sarah, where are you calling from? I am calling from Iowa. Iowa, beautiful. What part of Iowa, Sarah? Here we go.

I don't want to be more specific for reasons that will become clear. I just lived in Iowa. I just lived in Iowa City for a while. We know. We know, we've heard it. We've heard it. Look, Sarah, we're going to get him. Sarah, Sarah, we've got to cut Jake up. Who cares, which is what the bar said in Iowa.

We've got Jake, you've got me. We have a great guest who's going to help you out today. We have the fantastic Cal Penn is joining us today. How are you, Sarah? Good to meet you. Oh, my gosh. to meet you. Yeah, so step it up, Sarah, wherever the hell you are. Okay, yep, got it. Lock in. So what's going on, Sarah? What can we help you with? Okay, so I am an attorney at a

small firm. I will tell you were in like one of the bigger cities in Iowa, but a pretty small firm there, seven of us attorneys. Probably Des Moines. I am adults. Jake, I think she's trying to be general. It's not, can neither, can neither confirm nor deny. Maybe Aims. I will say, it sounds like you're confirming, but go ahead. She's actually in Nebraska. Wait a minute. I'll tell you this.

Jake, it would never be Aims. Okay. Then it's, then it's, then it's Des Moines. Wow. Okay. You're an attorney at a small firm. Seven attorneys. You're in Des Moines.

I'm the youngest attorney, but I'm also the only female attorney at the firm, which honestly works out great for me. Like, they're all. the other attorneys are all male between maybe like 40 to 60-ish. All of their, there are five partners. So five of them are partners, but then there's me. And then there's one other non-partner co-worker. He's maybe 40 years old.

We can call him Connor. Okay. And Connor is a, he's a great guy, like super lovable, hilarious. He is single, single, single. never been in a relationship for the entire time that I've known him and I think for like as long as he's worked as a firm. He, you know, has no kids or anything like that. And but he does seem, but he is a little bit awkward. But he seems self-aware about that in a way that's kind of surprising. Like he seems like he makes jokes about it sometimes. But the main issue is he seems to own. He seems to own. He seems to

one pie, like one single size. And which is normally not a problem. Yeah, you don't, like, you don't need, I don't know, maybe you don't need more than one tie. I don't know. But he owns one. And the problem with this tie is not the pattern.

Pattern's fine. It's that I'm pretty sure it's an adolescent-sized pie. Like, like, like. Oh my God. That's amazing. I will admit that I'm out of my depth here. Like, do they make different size? Presumably they make different size.

Yeah. Yeah, look at Trump's tie. He's got a little boy's tie. Fair enough. Yes, that's right. Well, this is like way worse than Trump's tie. This tie is, um, right, right, right. It's so short.

It's like almost clownish. I mean, we're talking like it comes, it comes. inches. It lands inches above his belly button. Oh my God. Crazy. And this is not a stylistic choice. You never know. Good bait.

He has kind of a beer belly. And so the tie just like the end of the tie just kind of rest there. So it's like it's worse. It's drawing attention to it. Right. So. And so here's the thing. We are like the Midwest, the legal profession, the Midwest, at least in Iowa is fairly

casual. Like we don't wear suits every day. Most of the days at the office is pretty casual. But, you know, when we have to wear nice things, we have to, we're in front of like a judge or something. You know, we're doing a deposition or we're appearing in court or something like that where it does kind of matter. And so every time he has one of those more serious things, he whips out this. Am I let's wear on this podcast? Yes.

Yes, of course. Okay. He whipped out the same fucking tiny ass tie. And so, well, and here's another thing is I know that it's not just happening in, like, the professional context because a few years ago, his dad passed away and some of us went to the wake. And Shana, Carter, is at his own father's wake in this tiny child's time. Hey, Sarah. You know what I like about how you've done this setup?

You've switched it to a setup into we're all having brunch. gossiping. It started off as a setup of a podcast, and now I feel like I want to lean in and go like, that's insane. We are now just gossiping. Brunch gossip is one of my favorite things. Well,

you have turned into our friend Steve Burke because this is the zone he just lives in. Well, you didn't talk about food enough, but yeah. I know, but this is the feeling. It's like, okay, so what is this guy's name, though?

Connor, we're calling him. We'll call him Connor. Okay. That's not a real name. So Connor, single, no kids, he's awkward, he's got one tie, it's a boy tie, inches above his little belly. He wears it all the time. It's not professional, but he also wears it at home to like if he's got to do something like a wake, which is a nightmare.

So Sarah, what is the specific question we could help you with today? How do I get him to stop wearing the tiny tie where an appropriately linked. pie without embarrassing him. I mean, I got the easiest pitch in the world, unless anybody wants to go. Could somebody go first because I got an easy one? Gareth, you got anything? I got an easy one too.

I mean, I got an easy and a hard. Cal, you were going to jump in. Yeah, well, I have a question and then a suggestion. Sure. Does he have tiny hands? Hmm. No. I'm picturing a ventriloquist dummy.

I am a happily married woman, Cal, so I haven't looked at his hands. Sure. I would just be... What? What's that? What's happening? Cal, normal question, Sarah. Weird response.

Crazy answer. Your husband's got hand envy? I don't think he's talking about does he have a big dick. He's talking about does he like to tie the tie because it's little. It's easier to marriage. I'm imagining if he's got tiny hands that he just needs a... He's T-rex. He doesn't want to deal with all that fabric, you pervert, Sarah.

Yeah. How is working? Check it out, hands. Honey, you're drunk. And then the second question is, do you think he's hung? No, it's just the, it's just the question about the tiny hands related to the tie.

But the real suggestion, the thing that like, I think before moving forward, I, like, you need to know why, what's the deal with that tie? Like, did his late dad gift him the tie? No, I would not,

I would not say this. has anything to do with deeperness besides he's got bad fashion. And I'll say that because, well, ties aren't like underpants in that you don't have to change him. You can, I don't remember the last time I've washed a tie. I literally don't know if you can wash a tie. Right. Like, I think you go, you wash your suit if you're going to get it, you know, dry clean. Yeah.

The tie just goes up. So you go like, you got one tie that works. He's single. There's no partner in his life going like, so Connor, what do you think? about looking a little bit better. He goes like, there's no sex in my life. A tie is just what I need to wear it. I got one.

It's also, it is a problem. It's tough because I do think you're right. It's a really weird thing to bring up. But I cannot imagine a guy looking like Chris Farley in front of a judge and feeling confident about slam dunking a case like that. I think your first pitch is probably what I have, which is, it's the holiday season. Exactly right. I mean, what a time to just give him a time.

We give him 12 ties. Yeah. All long. Yeah. We don't over-garet. We give men's ties that are normal size. Yeah. Okay, that was, so my husband and I have been brainstorming about this for quite some time.

That was one of the ideas. But the thing, I have a concern, and I have no evidence for this, but I'm concerned that he doesn't know how to tie a tie. Like, he tied this one in 2010. I get what you're saying. You give, then you, then pre-tie the ties. Give them 12 pre-tied normal-sized ties. Or you could give him some ties and let him bring up this issue when he's not wearing it.

I have an idea. We could solve that. I don't know too. Go ahead. I'll go, actually. Okay. We create a fake charity that you ask all the lawyers there to donate a tie. because you are, it's like a fun thing you're sending,

it's called like the tie giveaway and you're sending ties to this organization. Because he only has the one tie, you say it's a tie off your back day. So whatever tie they're wearing. I mean, but Jake, very quickly, I hear you. But imagine if you're not a partner at a law firm and you're walking around to people above you where you want to be a partner someday and you're going, hey guys, it's me, Sarah. Hey, love it here.

Can I get everyone's tie? But, yeah, that's true. Let me add one factor that maybe will factor into your pitches. So the partners know. And we've talked about it. I've gone to them and then like, guys, what the fuck are we going to? This is perfect. So, Sarah, this is not hard.

But then they don't do anything. That's okay. Sarah, I think you're doing something. Yeah. So what's your thing, Cal? You just say, buy them a tie. Buy a tie. But either buy him one tie or buy him 10 children's ties.

Let's not do the 10 children. Not even like, not it like he's breaking out of jail just slowly down to the Yeah, the same type of tie that he has, the same size, just a different. I, I, okay, I got one. And I, look, the fact that the partners know, I think, does open us up to a different world of pitches because, you know, there are options where we could float an email out there. We could scapego to another one of the partners. Come on, guy, change your tie every once in a while.

We could do that. But why not? Does he drink coffee? That's a great question. I don't know that I've noticed if he does. He definitely drinks Diet Mountain Dews, if that told me. Boy. We really, this man is honestly, it's tough.

He's like a gamer. Here's my big video gamer. This is crazy. I do not want this guy representing me. Sarah, we all knew that before you said it. Yeah, well. There's some dead giveaways. Getting tougher.

But my pitch would be this. You get him a coffee. You get the lid and you take a pin and you poke a couple holes in the top of the coffee so that we're pre-poking a spill on the tie. And at that point, you can go, oh, my God, I've ruined your tie. and that's where you come in with the Mayaculp a tie. Two days later. I had written something similar, Gareth.

I had written grape juice. I think yours is smoother, but I would do the... Spill. Wow. She does the Harlem Globetrotter. Do the Harlem Globetrotter, then feel so bad. And then the next day, gift him a new tie and go, I am so sorry. Don't hate that either, to be honest.

But, I mean, we are putting a lot on you, Sarah. Go ahead, Cal. I think you can just gift him a tie without reason. And if you need a reason, then just get six other gifts for the other people you work with. How about if their ties? How about if you get everyone you work with a tie? Yeah, it's all dudes anyway. So you're giving everyone a tie.

You could do similar, you could do picks. And you could even tell the partners, hey, in the new year I'm going to get everyone a tie. The next day, everyone wear the tie. Please, for me, whatever. No, you do this, Gareth. You get everybody for Christmas. you get everybody a tie that they all kind of match. And then you have your closest friend, another lawyer, go,

hey, guys, let's all start wearing these ties. I think it looks good that our ties match. Okay, but let's say they don't like that. I would say just have the partners comment on how good his new tie looks. So he feel like you just pre, you know, we pre-bake it. Get him a tie with a logo on it. this custom made and the logo is a picture of him wearing his tiny tie? Or to that point, what if we, what if we give him his initials on the tie or something?

Like on the back, if on the back, you give him like a little bit. His initials, it's kind of special. Everybody gets their initials. Everybody gets their initials. A great gift to give everybody is a beautiful full-sized tie with their initials on the back. I like that. And then every time he wears his little tie, go like this. Oh, did you not like my tie?

Oh, yeah. And he'll go, I love the tie. And you go like, oh, okay. And just pretend you get your feelings hurt. And he'll go like, ah, shit. I love my mini tie. But I got to wear that because I don't want Sarah to get her feelings. Grape juice.

Grape juice. This is the other thing I'd say. If this, if he, for some reason, doesn't wear that tie, I like the Jake, like let's foam the runway here a little bit and get that. So the partners, we're all going to wear. our ties, you know, whatever. And if he for some reason doesn't wear it, then you're right. He doesn't know how to tie a tie. I think at that point, you can step in, explain to him. It's very easy. It's a better look. And you'll show him how to do it. But I also think if you're trying to show the

people that you work for, that you're good at problem solving and evaluating situations and getting through it. I mean, the stakes are a little high here. So I think we're getting you in a good zone. I agree. I think maybe pre-tying it is still the move just to remove that barrier. I think you're actually dead right, but I would then have, I would re, I would pre-tie all of them. Oh, yes. Okay. A uniform pre-tie situation.

And then, so they all have a very similar look and you just say, this is the gift and it's thoughtless to everybody as they go like, She pre-tied it, but it's a little method to the madness. Initials on the back. And then they'll know why. Like I can say why too. I can say, hey, this isn't because I don't think you can tie a tie. So my question to you, Sarah, is from Des Moines. What is he going to do?

Stop cross-examining her. Clearly, Des Moines. Leave her. What are you going to do? I am going to gift everyone a tie. But you know what I'm going to do? I'm going to gift everybody a tie. and maybe only put his initial on his to make him feel extra special.

Why? Or is that weird? Weird. Okay. If I'm him, I go like this. Did you guys get your initials? And they all go, no, just you. And I go, why?

Yeah. And if your husband doesn't like you looking at other men's hands, I mean, specifically initially one guy's eye. I would go, why does mine say JJ, nobody else is? And everyone goes, I don't know. I'll go, that makes me feel uncomfortable. Okay. If everybody gets it, I'll be grape juice.

I'll never think it. But if it's just me and I'm a weird single guy who games with little hands, I'm getting weirded out. Okay, okay, I think you're right. Okay. So I think gifting everybody a tie, and then I think if he's still, like, pre-tied, if he still doesn't wear it, I think I have no choice but the coffee grape juice. Yeah, I think you're right.

It's good backup. Pre-coffee grape juice, I think you have every right at that point to say to him, did you not like the tie? I think you're right. Can I at least see, and you go, guys, can I see you? You know what you do then? Here's what we do before grape juice. If you give him the tie, he doesn't wear it.

You one day go, hey guys, can everybody come in on Friday wearing the tire next time we need it? I'd like to take a group photo. Then maybe once this creature or habit puts it on, he'll go like, hey, look at me in a man's tie. Look at me looking not so bad. And then compliment the hell out of them. You could say that the person who made the ties likes your idea for a Christmas gift and wants to see everyone wear it,

you know, something like that. You know what you could actually do? This is a real easy way. We forgot about the fact that he's single, no kids, awkward in games a lot. You know what he doesn't get is a lot of compliments from women? Yeah.

I would say the day you give it to him, you say, hey, would you try it on and it's already pre-done? He puts it on and then go like, whoa, Conner. Yeah, I think that's right. That looks so. So, and use the term sexy. Yeah.

And then cover your mouth like it slipped out. But just go like that. Or go like this. Or do it playfully. Go like, whoa, that color, you look hot. And then, oh. And go, watch out ladies of Des Moines. Don't tell my husband I said that.

And I'm not in Des Moines. Yeah. And then go, but for real, you look great, man. That's a good looking tie on you. Okay. Because a little bit of a compliment. I mean, I'd like to lay it on quite that thick. Sure.

I can do. These are options. I think I can do some... All right, Sarah, let's try this really fast. Cal, do you mind being Connor? Yeah. You just got the tie. Sarah, let's see how you're going to do it.

Let's just get a taste of this. Okay, so he just got the tie. You just hand it. We're actually, walk in. Let's do the whole thing. Walk in and give him the tie. It's right after Christmas break. Sarah, hang on.

I'm playing video games. Hang on. Hang on. Hang on. Hang on. Hang on. It's a kid. All right, I killed this guy.

Hey, Connor. Hey. I hope your holidays went well. I've got a bit of a late gift for you here. I gave one to us to everybody, but I really hope you like it. Oh. Oh, it's a tie. Yeah, you know, I noticed that you have sort of the one that you wear a lot,

so I figured you could use the new one to add to the rotation. Oh, wow. Thank you. Thank you. And I take the box and I start to put it in the drawer, but. You know, I'm actually, this is really embarrassing, but I'm really excited about these ties. So would you be willing to try it on and just show me how it looks?

Oh, sure. This is weird, Sarah. Sarah, here's, here's, here's, weird. Here's where you got off on the wrong foot. And this is why we do this and why we're lucky to have Cal here is because you don't want to, we're trying to avoid the confrontation that he's just a one tie guy. We never, you gave it to everybody. The whole structure here is that you're going, everybody gets one.

everybody's normal. Agreed. You too, Connor. I noticed you're also a bit of a fucking weirdo wearing a boys tie. Hey, freak. Let me see it. Cut that out.

Let's try. And not a very, it would be weird for me if someone gave me a gift and went like, do you mind trying it on? I'd be really excited. I'll be like, what, I got to dance now too. Get out of here. What's a not weird way to ask that, though?

That's a hell of a question. I think this. Let me see it on you. I don't think that's crazy. I think people, when they give you articles of clothing, I do think most people are excited to give and want to see you happy to have. Yeah. And then you can you can you give it to him on a day that he's wearing a tie?

Do you know when he's going to give like a deposition or something? Great question. Then you say, hey, I have this gift for you. He opens it. It's a tie. You say, oh my God, this would look so good with the outfit you're wearing. Yes. Could you switch it?

And then tell them to go to the bathroom and look at the mirror and then, oops, I spilled mustard all over your old time. That's an insane ending to a great pitch. What the hell happened at the end? I ate a sandwich over the old one while you were gone. Everything besides the insane mustard thing. You got to get rid of it. No, we don't. No, we don't.

We're not doing that insane ended. So Cal and Sarah, can we go once more? Sarah, will you be influenced by Natalie's take there? Can we just see what happens? Hey, Sarah. Yeah, I think that's a great idea. How was your break? Oh, sorry.

Hey, Connor, my break was good. How was yours? Good. Good. Well, listen, I know I'm a little behind on the holidays here, but I got everybody a little gift. Here you go. Oh, a tie. Thank you.

Yeah, you know, I got, you're welcome. I got them for all the other partners as well. And, you know, it actually, I noticed you must have like a deposition or something today. Yeah. Oh, awesome. Listen, y'all, I'm excited about this gift. Would you be willing to just try it on for me? Yeah, sure.

Does it not look too big? It's an enormous time. It looks like an elephant's trunk. It's just for a man. This is for a giant. I'm just a man. You know, I'm not really sure. My husband helped me pick out the sizing,

and he said this was like the normal size. All right, Sarah. Yeah, this is golden. And now he comes back in wearing the tie. Love. And then while he's up in the deposition, I snag the other one, light it on fire. Sarah. Sarah, no.

Sarah. We cut that. We cut that. But now let's, go ahead, Cal. You got to give him a compliment once he puts the tie on. Yes. So now, Kyle goes to the back, or Connor goes to the bathroom. He comes back wearing the tie.

He's a little insecure. It's not the one he likes. Connor, that looks really nice. Good luck on your deposition today. I hope it goes well. A little bit more. More, yeah. That was, if I'm Connor, I go, this looks terrible.

Okay, okay. All right, Connor walks back in wearing the tie. Okay. Wow, Connor, that looks so good. Oh, my gosh. Well, good luck on your deposition today. I know you'll crush it. Sarah, you mind getting a little specific in the compliments?

And I don't even hate you complimenting the new length of the tie, honestly. Yeah, or what it brings out in his eyes are, holy cow, killer. Okay. Well, Connor, wow, that tie looks so good. The Navy Blue really complements the N in your Nike Monarch. That was mean. What? You can give him the confidence directly.

You can say something like, Connor, that tie. looks amazing. You're going to crush your deposition today. Yes. Okay, okay. We're just confident. Just like, yeah, yeah. Yeah, because now you're killing it. All right. Connor walks back in the room.

Wow, Conner, that tie looks so good, man. Good luck on your deposition today. You're going to crush it. I'm happy with this. Is everybody happy? I feel good. I feel pretty good about it. I think we're in a good spot. I think don't be afraid to really make him feel good in that moment. The Nike Monarchs, we could do a whole other episode on that, but we got to go. And then, Sarah, will you, are you going to do this before Christmas or after?

I don't know if I'm going to be able to do it before Christmas. It's fine. First day back. Then it's a gift for the new year. Totally. There you go. Will you follow up with us as soon as it happens? This is something I think is going to work and I want that bell ring.

Can I suggest one more thing? Yeah. How about because your husband helps? helped you pick out, which I thought was a great little detail. Get a picture for the husband and that picture secretly for the show. Yeah, totally. That's a great idea. Thank you, sir.

That's a great idea. I think that's right. Okay. Thank you, Sarah. Good luck. Good luck, Sarah. Thank you so much. Enjoy, Des Moines, for sure. Bye.

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This episode of We're Here to Help is brought to you by Hungry Route. You've heard us talk about Hungry Route before, so you know how much we love it, because it truly simplifies our lives. As a busy parent, it's been a game changer, saving time, reaching health goals, and reducing stress to do all my weekly food shopping with hungry root. It makes it easy to make sure that I'm getting good nutritious food for the family in one-stop shopping. I got a vegan chorizo taco that I had last week and just truly fantastic.

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and use code here to help. That's Hungry root.com slash here to help. Code here to help to get 40% off your first box and a free item of your choice for life. Hello. Wow, that phone was not on your proximity at all. Holy shit. Oh, my God.

The podcast. Can we get your name, please? Yeah, Jim. Hi, Jim. How are you? All right. How's it going, boys? Great, Jim.

How old are you, roughly, buddy? I'm 42 years old. Hey, Jim. Did you ever go by Jimmy? Yeah. Not really, no. James? No, growing up, the grandparents would call me Jamesy.

You know, cute. Yeah. It's just mostly Jim these days, huh? Yeah, yeah. I mean, I'm 42 years old. My brother gets mad at me. when I call him Danny. What you do?

I do on the podcast. My brother's name is Dan, and he said, hey, my man, ever since I've been eight, nobody calls me Danny, and I'll go like, my guy, Danny. And now on the largest platform he's had, he's Danny. That's nice of you. Jimmy, where are you calling from, bud?

James, he went to go? I'm in the western suburbs of Chicago. grew up in the city. Awesome. Okay. Well, Jim, you've got Jake, you've got myself, and we have a great helper today. We have Cal Penn with us, so confidence levels high. How you doing? Good to meet you. Nice to meet you. Yeah, I got some good helpers here.

You're damn right, you do. Well, speaking of which, what can we help you with, Jim? What's the problem? All right, so about two years ago, I gifted a ring to my wife. I think it's a nice ring, one of those websites. design it on your own. I think I did a bang-up job. Sentimental. We have two kids. Did the birthstone for each of them on either side of the diamond and then, you know, an inscription on the inside of with their birthday. So something sentimental, nice. I don't remember when exactly, but a couple weeks ago I clocked that she's not wearing it anymore. Still has a wedding ring and band. You know, no money. problems really that are dire that would lead her to pawn it.

So I'm kind of thinking either it fell out of favor or she lost it. What I think I could use your guys help with is, you know, sweet life. She's the best. Obviously, you know, we're not afraid of confrontation. So she would have mentioned something to me if she wasn't feeling bad about it. So, you know, I guess what I need to know is do I approach the subject with her? I leave it alone because she obviously feels bad. I'm not trying to, you know, bury her or anything like that.

But, yeah, that's interesting. Well, first things first, Jimmy, let me say. I didn't hear Chicago at first, but now I do. Once you brought up the term your wife, you went like, hey, my name is Jim, I'm 42, and then you went, I got her a ring, my wife. Got body a egg. I was eating sausage with you going, I feel pretty nervous, but I'm excited about this weekend, boss.

I mean. So let me just paint this picture again just for my head, because I got a little confused with the wedding ring versus this. So you got your wife. What kind of ring was this? Oh, it was like a birthday gift two years ago to celebrate. We had our second child. We're not going to have any more.

We made that decision. So it's just a nice birthday gift. And we didn't need to get to the second. Where does ring number two, where is she supposed to wear it? Right hand ring finger. Okay. So you are covering up both ring fingers. You got the wedding on the.

left, you got the gift on the right. The left ring is still on. The right finger mysteriously is empty. Yeah. Question is, what do we do now? How long has it been not on her finger? Yeah. Yeah, that's a good question.

And I noticed it maybe a couple weeks ago, but I can't really pinpoint an exact date being somewhat oblivious sometimes to this stuff. Can we hear you say Caleb Williams is our greatest quarterback? We should lock into the problem. I know, but I just have never heard the Chicago accent so pure in a while, but I haven't heard them say Caleb Williams. I like Caleb Williams is a great quarterback, and I'm excited about Ben Johnson. Can we hear that the way Chicagoans would say it?

Sure, then we'll get back in. Caleb Williams is the greatest quarterback, and I'm really excited about this guy, Ben Johnson. Yeah, that's pretty good, man. I feel excited too. Okay, back to it. where we were. Hey, Joe, Jeff Park, North West Side,

sister-o and Montrose, you know? By the way, this is the only ring Chicago fans should be focused on. Hey, Garrett. Yeah, Jimbo. Hey, Jimbo. Easy, pal. I got something. What is it?

I got a pitch. Okay, I would say what we need to do, I think, and look, yeah, you can simply ask her, but you're calling the show, so you don't want to. So, I think we should make an organic, moment where you can sort of discover it in front of her, and that kind of covers you for why you mention it. And the best way to do that, sort of to where Cal was going, is find out when she was wearing it. So go back through your pictures, take a look at your pictures, take a look at the last time on your pictures where you see your wife wearing this ring. It's clear. And I would say one

the two things, either for some reason manufacture a moment where you've got to look for some picture in your phone or maybe even better is find a nice picture of her, of you and her on your phone, get it framed, and then give it to her for Christmas. And in that moment, you can make the connection that, hey, where's that ring? And set it up like an organic gotcha. I got something, Cal, you got anything? A lot of silence on my pitch, I'll be honest. I like that pitch a lot. I was taking it in because I felt like it was sweet.

The reason I liked that it was sweet is when I heard you telling the story about the ring, it was very sweet how you are so mindful that you don't want to hurt her by asking her. And I feel like if what you're saying is, let's say she misplaced the ring and it's like been eating her up for the last six months or whenever she lost it. I think there's an opportunity to talk about gifting her something that has the same sentimental value because obviously she didn't mean to lose it, right? And so, like, there's a way to do it that extends that kindness

that I think the idea of that picture sort of brings out. I got to say, Jimmy, is another guy from Chicago. I don't like any of this. Yeah, I got to tell you. I could tell that Jake's a little agitated by the emotional understanding. Well, no, Gareth is just doing a new thing where he's trying to be a sweetheart. What are you talking about?

I'll be honest, when Cal said my pitch back to me, I was like, that's way nicer than what I was doing. I was like, oh, yeah, exactly, Cal. Jimmy, here's what I would consider doing. Yell at her. Go ahead, Jay. One day, walk in the house. What do we call in your wife? What's her name?

Jesse. Jesse go like this. Hey, Jesse, Jesus Christ, I got a fucking pickle I want to talk to you about, baby. and she'll go, what is it? I'm over at the Jewel Oskill. You'll go, let me tell you what it is, dear. Somebody must have broken into the damn house and stole stuff. And she goes, what are you talking about?

And you go, I'm missing things from my fucking jewelry cabinet. She goes, what do you mean? You go, my necklace is gone. Five of my golden dollar bills are gone. Someone's stealing. Are you missing anything? And then she could say, I think somebody stole my ring

and now you're in it together you give it up. What is happening? What is that? Yeah, Cal, please. This is an episode of law and order this is sure. Honestly, it's the wildest

way to think that this all of this says, hey honey, there's been a murder at home. What we're trying to get, Jimmy, and don't listen to these guys, they're not from Chicago like us. We're trying to get.

get her to believe somebody. Somebody broke in and stole stuff from you. And then you're saying to her, I don't know if it's true, but can you relate? And what we're hoping for her, she goes like this. I got to tell you, I think somebody, if that's true, I didn't want to say this to you, but you know that ring you gave me? I don't know what happened to it. And you go, I think it's the fucking thief.

I think if you're going half, you can't go halfway. You got to have a buddy come in with a fake gun and a ski mask while you're both home and just take shit. And then when you're doing the inventory, go, oh, babe, I think they took your ring. Actually, that's interesting. That opens up a new realm of a new way. So what if we do this? Okay, what are you going to say, Jim? Go ahead.

I was going to say, I got some cop buddies who might be able to get me a police report or something like that. This is what we're talking about, Jamesy. What I would do is, to Cal's point, what if you employ a friend? What if a buddy of yours who's married comes over while he's there, you're all hanging out, and he says something along the lines of, I actually want to get Judith this ring, you know, something that's like, you know, an anniversary ring. I'm thinking I could do it for the holidays or her birthday coming up. And that's when you go, oh, that's exactly what I got for Jesse.

I got Jesse. Oh, my God, where's that? Where is it? Like that. That's really sweet. You know what we could do, Jimmy? We could use one of your. cop buddies to contact your wife and go.

This is crazy. All right, Gareth. Then I'll stop. No, keep going. I don't know what you're doing. Do you want to stop this? No, keep going. It's crazy.

Okay. So I would have one of the cop buddies contact your wife and go. You know, there's been reports on the blocks of possible things missing and breakings. I just want to know, has anything gone missing from you? We're not doing anything official at this point. We're not saying anything is happening. We're just getting an inventory of what's going on on that block of yours. Because if she's actually misplaced the ring and doesn't know it,

she might not want to bring it up, but what she might be able to say is, yeah, actually my ring has disappeared. You could get the cop and her to discuss it, and then we could get info. If she says nothing, not the case, then she says to you and goes, have you heard about this? And you go, no, then we at least know, the ring is not missing.

But the fact that we have the actual Chicago PD who's a buddy of yours, who's not afraid to do like a Joe Pesci, a home alone type visit? You know I have a soft spot for home alone. This tis the season, babe. If you did it in person, if your cop buddy came over and was sort of talking about, something that just... I mean, I just think if someone brings up a ring or something like that and you're there,

that gives you reason enough to go, wait a minute. Is yours missing? Something like that. It's not bad. Where are you at, Jim? What are you kind of thinking? Yeah, you know, I'm thinking... The picture thing, very nice. I like the new leaf there, sweet Gareth. But I don't know how many, like, full-body pictures I have where she's, you know, the hands are involved,

stuff like that. I think the logistics of that, you know, might be a little rough. I think, I think, you know, my cop buddies, we go back, St. Pat's High School, so they'll hook me up.

Of course, thank you. But also, I think, you know, we got some holiday stuff coming up. I could maybe, I could maybe talk to, like, a family member, cousin, her brother's got a relatively new girlfriend. I could have him be like, hey, man, I could, you know, pull him to the side.

Hey, help me out with this. Say you're shopping for a ring for your girlfriend and da-da-da-da. You know what we could do there? You know what you could do on that, Jim? Is you could actually have your brother say to her and say, hey, can I see that ring that Jimmy got you? I want to get something similar to this girl I'm dating. Yeah, that could work.

Because that could be very clean. That's simple. Then she could say to him, don't tell Jim, but I lost the fucking ring. But if she gives it to him and we see it, then we can do a follow-up to this to figure out why she stopped wearing it. But I feel like this could be in two parts, man. I think part one is we got to figure out, is the ring available? Because if she lost it, sometimes it's hard to say, like, I'm such a fucking goober. I don't even know where I lost it, but I'm really embarrassed.

I don't want to deal with that. That's fine. And if that's that, we can get you out of it in an easy way. We could pitch a way to end it so it's not embarrassing for her. But if we know for sure she has it, then we figure out part two, and that is, why isn't she wearing it? Yeah. Did you say that's her brother or your brother? Oh, yeah, her brother, my brother-in-law, her brother.

Great. So that's easy. Do you think he would play ball with you? I think he would. You know, we're going to be out on the town for this big game coming up. on Saturday. There's Packers. I can have a couple of bruskees with them and

we can chop it up. You're drinking old style? You're going old style? You're going nice new beers. What do you like? You know, I like to mix it up, but you know, they just introduced yingling here in the Midwest for us. America's oldest brewery.

That's been in rotation. You don't finish tonight with a couple Mallorts, do you? You're not an animal, are you? Oh, boy. You know what? Actually, my dirt back. wife likes that stuff.

I can't handle it. I can't handle it. My dirt bag wife. What do you think about the rap song, Denahey? Have you heard that? Oh, love it. Serengetty. Serengetty, the best.

It's the best. So, Jamie, walk us through what you're going to do here, pal. I think I'm going to involve the brother-in-law. Okay. He's, you know, he gets it. I think, I don't think he'll, you know, rat me out at all. I think you get there. He'll help me out play ball a little bit.

Great. Like I said, he's got the girlfriend. Christmas is coming up. I think her birthday's coming up. So, yeah, I think, you know, like I said, chopping it up over a couple beers. Shopping it up. You can figure it out. You know what you also said on this call that means the world to me, and I realize it's a Chicago thing?

You said something affectionate about your wife that doesn't translate. Our show is international, Jim. But you referred to her lovingly as, I believe, a dirtback. And I just want to say, that's a term of affection. And it doesn't translate my dirtbag. Also, Malort. Enjoying the Lord at the end of the night is a shh back. My wife likes Malort.

It's an amazing line. That's a great t-shirt right there. That is a good character description. It is a great t-shirt. Cal, before we get out of here, what do you thinking about this? Are we right? Are we wrong? Have we missed the mark?

No, I like it. I think, look, if for whatever reason you don't feel comfortable asking directly, if you don't feel comfortable going through the jewelry box when she's at work, if that feels like it crosses a line, I think this is the next best thing. You've a great relationship with the brother-in-law. You're going out on the town anyway. It's a great opportunity to figure out what's going on. Yeah, and Jimmy, if she stonewals him and he can't get an answer,

fuck, man, the boys in blue could help a lot in this situation. Then we home alone. Yeah. Then we call in for backup. But before you call him for backup, call back in, okay? For sure. And then before we go, could you say thin crust pizza? No, thank you.

I'm from Chicago. Thin crust pizza? No, thank you. I'm from Chicago. Go bears. Go bears. Right there. Anything about the bears you want to say before we go, any party and worry.

Natalie, will you mute Gareth, can you? Okay. So, go ahead, Jim. I was just going to say, good, better, best. Good better best. Exactly what it's about. It's exactly a little. All season, baby.

It's going to be a lot of fun. Jimmy, follow up with us, please. Cal, thank you for doing the show. We appreciate you. Thanks for having me. It was a lot of fun. Okay, bye, bud. Thanks, boys.

Take care. Bye. We're here to help is hosted by Jake Johnson and Gareth Reynolds. If you'd like to be on the show, please email is your question at HelpfulPod at gmail.com. And if you want to watch video episodes of We're Here To Help, you can go to our Patreon at patreon.com slash here to help pod

to see our entire catalog. We're Here to Help is produced by Rabbit Grimm Productions, executive producers Rob Hollis, Jeff Porter, and Natalie Hollis, Associate producer Jesse Thurston, editing mix and master by Chris Fowler. Theme song by Oliver Raleigh. The cover artwork is by James Fostike,

animations by Andrew Strelicki. And if you'd like to see Gareth, do stand up on the road, go to Garethrenolds.com. Remember all of the advice, given on we're here to help, is for entertainment purposes only, and all listeners should be adults

and make their own decisions. That was a headgum podcast. All video episodes of season one are available now on Patreon, and season two video episodes will be available every Monday starting January 20th. Go to patreon.com forward slash

Here to Help Pod. Hi, I'm Drew Offal And I'm Dason Off Wallo. And we host the Headgum podcast, Two Idiot Girls. Each episode, we're discussing plenty of topics that you would be giggling at a sleepover with your weird cousins. We talk about all kinds of things like weird dating horror stories, maybe a really bad wedgy you had once, or even a show you're loving and anything in between. So you can listen to Two Idiot Girls on your favorite podcast app or watch full video episodes on YouTube. New episodes will be posted every Tuesday.