Let's Be Honest with Kristin Cavallari - Go On The Ice Cream Date — Dating Questions Pt. 1

Episode Date: January 28, 2025

Part 1 of these listener dating scenarios does not disappoint. We cover how everyone is over dating apps so how we can meet people in real life, how to approach men in the wild, how to tell if he's only looking to get some action, why it's ok that they're a bad texter, how to tell someone you have herpes, and we discuss if the wrong guys distract from the right guy. A word from my sponsors:YNAB - Listeners of Let's Be Honest can claim an exclusive three-month trial, with no credit card required at www.YNAB.com/HONEST.Bon Charge - Go to Boncharge.com/HONEST and use coupon code HONEST to save 15%.Cymbiotika - Go to cymbiotika.com/HONEST for 20% off your order + free shipping today.OLLY - Let's do wellness on your terms, whatever that looks and feels like to you. Find us at Walmart or Target near you or at OLLY.com.  Disclaimer: These statements have not been evaluated by the Food and Drug Administration. This product is not intended to diagnose, treat, cure or prevent any diseaseSKIMS - Shop SKIMS Valentine's Shop at SKIMS.com. Available in styles for women, men, kids, and even pets! If you haven't yet, be sure to let them know we sent you! After you place your order, select "podcast" in the survey and select our show in the dropdown menu that followsBILT - Start earning points on rent you're already paying by going to joinbilt.com/HONEST.For more Let's Be Honest, follow along at:@kristincavallari on Instagram@kristincavallari and @dearmedia on TikTokLet's Be Honest with Kristin Cavallari on YouTubeProduced by Dear Media.This episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct, or indirect financial interest in products, or services referred to in this episode.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

The following podcast is a Dear Media production. This is Let's Be Honest with Kristin Cavallari, a podcast all about getting real and open on everything from sex, relationships, reality TV, wellness, family, and so much more. And just a fair warning, there will probably be some oversharing. Welcome in, guys. How is everybody? I feel very official because I got my let's be honest cards to have at my house now too. And I just feel like, yeah, after a year and a half, we should do that. We should do this. We should make this official instead of always using

my laptop. I have a really fun episode for you guys, potentially a two-parter. We're gonna see how much time it takes to get through these, but I had asked my Instagram followers to tell me what's going on in the dating world, dilemmas they've been having, just issues and just things they wanna talk about. And every time I ask, I get so much great content, so many great stories.

So thank you to everybody who submitted. And the dating world is the wild wild west out there that is for damn sure. I experience it myself obviously. Having been in the dating world for five years and hearing y'all's stories and the issues you're having it honestly makes me feel a lot better. It gives me a lot of peace because these are all universal things. So let's have some fun. Let's get into it. Okay. Let's start with the kind of the dating apps and stuff. So it seems like everyone is sort of over dating apps, which totally get, I understand that. I, the one dating app that I did was I was on Raya last fall for probably four months or so and I only went on four dates from it. I

would say all really good guys though. I had actually met one of them previously like 15 years prior so we reconnected on there. I met three new people on Raya and one of the guys I went out with was a really good guy. I can honestly say a really solid guy and the other two were meh, but that's fine. You know, they all can't be winners. But one of the questions I got was about Raya and if is Raya a glorified hookup site? Is any guy really seriously looking for a relationship on Raya? And what I will tell you is, yeah, I think there are guys on there looking for relationships.

I think, I don't have experience on any other dating apps, but my experience on Raya is, first of all, it's actually not that great. I didn't, there weren't a lot of options is really kind of what I saw. So after I guess I had been through everybody, they start filtering all the same people to you again. And so what I realized in three months, I guess, maybe even sooner than that was that,

oh, the pool is actually not that big. And the issue with Raya is they will give you the couple people that are in your city, but they're giving you people in London and Switzerland and Australia. And you're like, that's great. But when am I going to go meet fucking Ken from Australia? Like that's not realistic. So that's where I got annoyed with it. And I went on a couple of dates. Let's see, I went on the three of the dates I went on. Well, I guess all four of the guys I went out with were, had a connection to LA.

Two of them weren't living in LA at the time, but they were, they had lived there. And they're, I think one of them ended up moving back to LA. But I don't know. I, yeah, I didn't think that there were a lot of great options. And here's my other issue with dating apps is that men are not good in photos. I will stand by that till the day I die.

And again, I mean, everything is about chemistry. It's about a connection you have with someone and you only know that by meeting them in person. I think someone on paper can be incredible and they can have all the same interests as you. But if there's no chemistry, it doesn't matter. So that's why I think dating apps are tricky or any online dating really. And so that's why I have vowed in 2025 to

meet someone in real life. And that's why I think other people are now feeling the same way. But I will always say Raya is, I guess no different than any other dating app except for, now everyone thinks because they had to be accepted they There's like this false sense of coolness Associated with it, which I don't like that. I don't like that at all, especially with guys and I don't know. I didn't think there was anything special about Raya. I would not go back. Let's put it that way and didn't think there was anything special about Raya. I would not go back. Let's put it that way. And so I don't know. But okay, so then other questions were, oh, but I know. But to answer that question, though, I do think there are people on there looking for a relationship.

I mean, I do. I think it just, I think it just takes the right person. Obviously, I think guys will be fuckboys until they meet someone they don't want to do that to or that they want to settle down for. And I think that's any dating app. I think that's also real life too. I think that's just our society. So someone said, I just can't do the dating apps anymore, but where do you meet people organically?

Where and how do you meet people organically? And then someone else said what is the best way to meet single men outside of the apps? And then someone also said how to approach men in the wild? Apps are trash. So I think it's about just getting out into the world. I'm such a homebody and so that's hard for me and I've also decided okay I'm gonna be more social. I'm such a homebody and so that's hard for me. And I've also decided, okay, I'm gonna be more social. I'm gonna start doing more things. I'm gonna start going places. I think it's just about putting yourself in the world

and putting yourself in the world that you would like to meet someone at, meaning don't just go to the clubs and expect to meet your dream guy. I think if you're serious about a relationship, I think places to go, gyms, I just realized. So I've been fortunate enough to work out at my house for, I mean, a long ass time, I don't fucking know.

But when I was in New York this past fall, Justin and I went and worked out at Equinox and I was like, what in the fuck? Why have I not been going to a gym? There were so many hot guys. It was New York, I not been going to a gym? There were so many hot guys. It was New York, I'll give it to you. There were very good looking people in New York.

But I was like, okay, no, I need to start going to a gym. So it's things like that. Go to the coffee shop that you like, but sit at the coffee shop, bring your computer, do some emails, do your work at the coffee shop. I've always heard hotel bars are a great place to meet guys. So if you're traveling, especially definitely New York, LA, Chicago, some of these bigger cities,

go to the hotel bars, Nashville, even in your own hometown though, like go find the nice hotels and go get a drink at the bar with a girlfriend. I think happy hour is a great time for that. I mean, and I will always stand by if it's supposed to happen at will. And that can happen at the grocery store. It really I think sometimes it's just right place, right time. But what are

other things that guys like to do? Well, I have I have joked that I think, you know, going to the driving range could be a great option. Guys love to play golf. So get around the golf course somehow, you know. Maybe you even just go to the clubhouse and get a drink. I'm not even kidding. I think these are great options, which as I'm saying them out loud, I'm like, great, I need to do that too. So I think it's just getting in the headspace of a guy

and like, where do guys go? It's just about putting yourself out there more. Which is you know I need to take my own advice quite honestly. And then how to approach men in the wild. Okay so you have to have confidence and we've talked about this guys. If you have not listened to my episode on confidence go listen to it because it is sometimes it's just about faking it until you make it. So if you're... Well this just happened. I'll give you guys an example. So I went out the other night with a group of girls. Really fun great girls. Actually Caitlin Bristow, who

I adore. She's one of my good friends. And a group of her friends who I'd never met. And I just absolutely loved these girls. Really fun, really outgoing. Some of them are from Canada. Canadians we all know are just the best. girls. Really fun, really outgoing. Some of them were from Canada. Canadians, we all know, are just the best. So we went out, we were on Broadway, and we were at a club, and there was a group of hot guys, and they were all sitting at the table that was adjacent to ours,

and this one of Caitlin's friends and I were like, these guys are so hot, and I said, this is what I suggested. If you guys don't know what zins are, zins are these nicotine pouches that you put in your lip. They're like all the rage right now. Like all the hot guys have them, right? I am not in any way, shape or form condoning zins and saying that they are good for you. I'm not saying to do them. I am just giving you an example of what I did. So I had a feeling these guys would have zins, right? So I was like, let's go ask them for zins. Sure shit. They all had fucking zins. They were all pulling out their can of zins and that started the conversation. And so, and I'm not, I'm not saying go pick up zining as a hobby. That's not what I'm

saying. But use something like that, you know? Like a conversation starter, an icebreaker, and then we got our zins and I was just holding mine in my hand like, okay, thanks, but what am I doing with my zit now? Which is fine too. Or put it in for literally one minute and then take it out. Or do a fucking zin. I mean, you could do a zin if you want to do a zin. But it's fun things like that, that show you're confident because you're able to go up and approach them. You're fun. You have a sense of humor. Like asking a guy for his in is fucking funny. You guys can take that. You can use that one. I'll give you guys that if you want to use that. Or I don't vape. I'm vaping. I mean, I have obviously,

you know, in my day after a couple of drinks, but you can ask a guy if he has a vape. Like I don't know. I'm just think I'm think I'm trying to think of something also that's not like nicotine related or bad for you though that you could ask. Have you guys seen that TikTok thing about sending a group of guys water shots? I think that's fucking hilarious. You could send guys water shots and then after they take them, you could be like, we were just fucking with you guys. That was water. But like, do you want to take a real shot? I think that's really funny. I think showing guys that you're fun,

you have a sense of humor, that goes a long way. And that you're willing to make the first step. I think guys love that. So that would be a good way to do it. And I think having a wing woman is a great option. I think I would be too scared, too much of a little bitch to go up to a group of guys by myself.

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So someone said I'm 45 and divorced. Two different men asked me on ice cream dates. I know, what is with ice cream dates and lunch dates? I hate a lunch date. Actually, I think I would prefer ice cream because it could potentially be quicker. I just honestly, and I'm not a big drinker, you guys, especially as of late, but I for a first date want to be able to have a cocktail. I'm sorry. I just do because it calms everyone's nerves. I want to be able to have a cocktail

or to do something active because I do feel like doing something active, it just sort of, there's like this immediate distraction and it kind of puts everyone at ease too. So even like going for a hike or something, like I would go for a hike as a first date. I really would, I know not everybody would, but I would do something like that.

I like being active, I like doing stuff or I wanna just go get a drink. And I actually prefer just drinks over dinner for a first date. Because eating in front of someone the first time when you're first getting to know them, I'm sorry, it's just kind of awkward. And it's a longer process. So if you get there and you don't like them, it's like, Oh, no, no, I have to have a whole dinner with them. I love a drink that turns into dinner. Those are great dates. You know it's going well when the drinks turn into dinner. But you could if someone, it's funny because actually one of my Raya dates you guys told me that he takes girls on ice cream

dates. I did not do an ice cream date with him, but he did tell me that he takes girls on ice cream dates because he said, if you can't have fun having ice cream, then you can't have fun doing anything. Which I guess sort of makes sense. Also, I just think it's a cop out for guys. It's like a cheap, easy way. But again, you have to think about guys too. I mean, they also wanna know

if they are gonna be into you or not. I don't think an ice cream date is the worst. I don't think it's the worst. I don't think it's the, it's definitely not the best. I'd rather go on a fucking coffee date though if we're just being honest. Ice cream seems kind of young. No, I would I'd be like, well, let's just get coffee instead. I don't know. I don't know. Sometimes guys need a little guidance, which is not ideal. We really, I think us women, we want to be courted, we want to be chased a little, and we want a guy to put an

effort and be like, I'm gonna, of course, we want every guy to take us on the most amazing romantic date. That gets a little tiresome for guys, I'm sure, and expensive as well. So I can appreciate where they're coming from, but I don't know, ice cream? At least, like, let's just go get drinks. That's, we can all just go get a drink, you know? Although we are living in a big sober movement right now too. So that can also get a little dicey. Maybe the guy is sober and that's why he wants to go get ice cream.

I think you should go on the ice cream date. There's a whole lot of nothing to just go on that ice cream date. Okay, here's another one. This is very funny. Man sent me his penis picture before the first date. Yeah, I mean, damn that is aggressive. That is so aggressive before the first date.

But here's the deal, ladies. That just means he's just trying for a hookup. He's looking for a hookup and that is it. That's it. Otherwise, why would he send you his dick pic? for a hookup and that is it. That's it. Otherwise, why would he send you his dick pic? There's one reason and one reason only. I had a guy send me not a dick pic, but it was like a picture in his boxers. I could like clearly see the outline of it after two dates. And that was like, whoa, I thought that was pushing it too.

Yeah, I don't know. I think a guy initiating the photos is never a good sign. I think really good guys, A, will not ask for photos or at least not for a long time, I think. I think the girl should be the one to like first initiate the sexy photos and take it upon herself to do it. I think the girl should be the one to like, first initiate the sexy photos and take it upon herself to do it. I don't like when guys ask.

I don't, I don't like when guys are pushy about that. Like let the girl just do it when she's good and ready. And really, it shouldn't, that shouldn't be happening until you're like in a relationship, I think. But maybe I'm a little old school in that sense. I don't know. I don't know. Yeah, I don't know.

And everyone's different, but I think like real men respect that. I really do. I think it's a generational thing too. But real men respect that. What is your best advice about keeping other women away from your man? Example, coworkers.

Well, you can't. You cannot keep other women away from your man. I am sorry. And if you're trying, you are setting yourself up for failure and misery your your man. I am sorry. And if you're trying, you are setting yourself up for failure and misery your entire life. I am sorry. Also, that is a surefire way to make your man

wanna run the other way from you. You cannot keep your man on a leash, ladies. It just makes them want to run the other way. People respond really well to trust and freedom. Now, if a guy is giving you a reason not to trust him, that's another conversation. But if this guy is just going about his life and there's never been issues with cheating or lying,

this is about you and you need to let this man live and breathe a little because I'm telling you it's gonna end up hurting you in the end. This, we cannot be treating our men like this or the guys can't be treating women like this either or women and women like can we I'm not always going to be politically correct and don't shoot me okay I'm not just I'm I'm just speaking really from my point of view my place okay I don't care if you're in a lesbian relationship I don't care if you're in a lesbian relationship. I don't care if you're gay. I want you to be with whoever you want to be with, but I'm not going to hit every single one every time I talk about things. Okay? I'm sorry. So anyways,

I think if a man is making you feel like you can't trust him, well then that's another conversation. And I also think women can be really shady and women a lot of times, some women, there's a specific type of woman that likes to go after men that are married or in a relationship. And that is the most fucked up thing on the planet, but it does exist. So I have empathy for women who, you know, there's a woman coming after your man, but we need men who can set boundaries with these women and tell them no and have a fucking backbone who don't need the attention from other women because the problem is if these men are feeling insecure and feeling

like they're lacking something, they will find validation from other women. And that's just the harsh reality. I do think a lot of times, not all the time, I do think a lot of times cheating is to fuel the ego, it's to boost the ego, it's even flirting. I'm okay with a little flirt though. I got to be honest. I don't think flirting is the end of the world.

I think with a coworker, that's a little dicey because it's someone you see all the time. But I think going out once in a while and having a little flirt, I don't know. I'm kind of okay with that because at the end of the day, if you can trust each other and you have that foundation, I don't know. I think it's okay to feel wanted as long as it stops there. And I would be okay with my man flirting a little bit too, as long as there's like no touching, no, of of course exchanging numbers. If it's just like a little, if the girl's like flirting with my man a little bit and he's like laughing and okay, I don't know. As long as he's not being the one that's like preying on the girl and like initiating everything. If there's a girl flirting

with him like okay whatever. I don't know because I want to be with men that I trust wholeheartedly I really do I think that's huge and I think we should start going for the guys who are secure and comfortable in their skin or they're not gonna make us feel like potentially they could cheat or like they wouldn't stop it if there was a situation. Okay guys let's take a quick break to talk about YNAB. You put so much time and effort into earning money, you deserve to spend it without stress or second guessing.

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but his texting communication takes hours. I think that's okay. I don't think that we should base people based on how they text. This is why I hate texting. So much is lost in translation. We start to get in our heads about stuff like this because also you don't want a guy who sits on his phone all day. We want guys who are working, who are doing things.

I don't like guys who sit on their phone all day. I also, to be fair, I like when a guy doesn't respond right away. Because then I feel like I have to and I don't know, I don't think this is bad. I think what we should be really focusing on is how they're, when they're with us in person, how they're treating us, are they attentive? Are they listening?

I think you could also, when you're in person, see if he's on his phone or not. I think that's a good indication. If he's always on his phone when you're with him, but then he takes forever to respond to you, like, okay, well, that's not a good sign. But I think if he's with you and his phone is away and he's being present with you, that's huge. And that means then he just does that in his life. I'm like that, I try to be like that.

I'm not always like that. And I have to be on my phone a lot for work. But when I'm at dinner with someone, I don't wanna be on my phone, even if I'm in a relationship. I'm like, he can wait. I think it's okay to, I think it's a good thing. I think it's a good thing. I think it's a good thing.

But again, you wanna make sure it matches up with when he's with you, you know, that it's not just him like playing games too. Cause I don't like game players, but I like a guy who is busy. Okay. How to tell somebody that you have herpes. Okay. So that's tough, obviously.

I think, I think what you should do is I think that you should wait a few dates. Obviously, don't sleep with the person. But I think when you've gotten to know this guy and he seems like a good person and it's someone that you want to continue to see and it's getting to that point where like you know that sleeping together is coming then I think you say I think you just sit down and it's you don't you don't do it right before you're about to have sex it needs to be like you need to make him dinner at your house or something and you know tell him during dinner or something and just I think you say like, Hey, I have to tell you something, you know, when I was 25, I, you know, dated a guy who gave me herpes. You know, I'm just making this up,

obviously, it's whatever your situation is. And, you know, it's something that I, I've had to live with. And, you know, this is my this is my situation, basically. And I think any good guy is going to respect that and realize how difficult having that conversation is and respect you for it. I have had a couple of guys actually tell me that they have cold sores on their mouth, which is a little bit different, but you know, similar, same, you know, basically the same thing. And how they told me was basically just that.

And they waited, they didn't tell me at first, which actually, they definitely kissed me and then told me, but that's okay. Again, this is a little bit different. And then they just, they told me, you know? And I know that those conversations are very difficult and I really respect someone who's going to be honest with me rather than me just finding out later, you know.

So, and if, if the guy is kind of a dick about it, well then he is not the one. Clearly he is not the one. I think I'm going to be potentially wrong on this statistic, but I think like one in three people have herpes. A lot of people have herpes. And so I don't know, I don't think you should be ashamed by it. Obviously, someone gave it to you. You know, I think the most important thing is being really careful and you not spreading it, you know, as much control over that as you have. And I think by doing that, again, it's just being really honest. And the right guy will not care.

I can promise you that. The right guy will not care. When do you usually wait to bring up in the conversation of where we are going or what we are? I don't. I don't bring it up. Well, I have. I have one time in my whole life and it was the first guy that I dated after my divorce. And I think, well, I did a podcast with him, Jason Walsh. He's, he was my trainer in LA. We did a podcast episode about it and we talked about that. But I had said to him, we were at dinner one night and it was after a couple months of us hanging out and I was like, Hey, you know, just, so what are we? Are we dating?

Like, what is this? That was the first time in my whole life I've ever done that. And he was like, well, just finalize your divorce, and then we'll, you know, we'll figure it out. Which was a nice way of basically telling me, like, we are not in a relationship. Now looking back on it. And he's still a friend, and he's still in my life.

And he knew that I needed to spread my wings and fly. I was not ready to be in a relationship. And honestly, that was one of the best things he ever did for me, thank God. If you wanna hear all about that story, you can go watch the episode with him. But I really take the stance of when a guy is ready, he's gonna ask you. I really take the stance of when a guy is ready,

he's gonna ask you. And I know girls who have made it official and they're still together and things work out and it's all great. I mean, the girl can do it. The thing though with the girl bringing it up, you have to know that if you ask a guy, what are we? And he is like, well, I'm not, I'm not, you know, I don't, I'm not ready to be in a relationship and you are, well, then you have to walk away.

So if you're going to ask or say like, hey, I want to be in a relationship. Actually, Nick Vial said this another episode from one of the first episodes I did actually, he said, it's not a question of like so what are we what is this? It's like hey, I'm ready to be in a relationship I would love to be in a relationship and then from there if he says great me too. Okay, great wonderful But if he's like, I'm not ready then you have to walk away Because you can't you can't say I want to be in a relationship. He says no and then you're like, okay a Guy will not respect you for that. But I really believe when guys are ready, they will make it official. That's

always been my experience. And so I wait for the guy to bring it up because I just feel like, I don't know, I feel like if that's a situation where I really stand by if he wanted to, he would. I just, I really, I really feel like that. And guys know pretty fast. Guys know in the first three months what's happening. I would actually say in the first month. I would say in the first month, a guy knows if he wants to date you or not. And I think guys typically make it official in that like one to three window range, one to three three window range. One to three month window range. I really do. I'll stand by that till the day I die.

I'm afraid the guy I hook up with distracts me from finding a real relationship. I feel this so much. This was me a couple years ago. I really get that and I think there's probably some truth to that. I really do. I think that in order for something new to come in, you have to close a door or you have to let go of that. Cause as much as we would love to say, hooking up with a guy is not a distraction, it is.

I just think it is. And I've actually never been able to do that. I have joked and it fucking of course went everywhere that I was looking for a fuck buddy in Nashville. I never actually had that. I've never just done that. I've never been able to do that because I have to have some sort of emotional connection

with someone, but yeah, I just, so actually, so maybe because I have to have an emotional connection with someone, it would be distracting for me. But maybe some women can just do that, it would be distracting for me. But maybe some women can just do that and it not actually become a distraction. But I still think it's taking up some of your energy and your time that could be going out and potentially meeting someone new. So I think, and I think, I think there's two ways to look at it.

I think if you're thinking this and this is in your head, then that's probably what's true and accurate for you. I would say if you're having these thoughts, then maybe end it so that someone new could come in. And I also think there are probably women who could do this and they don't think it is distracting them or stopping someone new from coming in and both can be true. I think it's just whatever, I think everyone's different in that sense. But I lean more like this listener that gave this is I do think that it would be a distraction. I just do because it's energy, it's your time, it's your headspace that is taking away from something else that could

potentially be. We'll do one or two more and then we'll stop and we'll do a part two. Okay, so the other person doesn't engage or get to know me. I'm always initiating the engagement. Well, my girl, I hate to break it to you, but that's because he's not interested in you. And listen, guys he's not interested in you. And listen, guys, this goes for friendships too. If you stopped initiating, would they ever reach out?

Give it a test with some people. I think you would be surprised that some people may go away. And you know what? That's okay. Those people should go away because a relationship or a friendship is not a one way street. It takes two to tango. And especially with a guy,

you do not wanna be the one always initiating. No, this actually kind of breaks my heart. Especially if they're not asking questions about you. That's, no, this just tells me that they don't care. And that makes me sad. I think we all need to be better than this. Guys are naturally hunters and chasers and you know, they I think if a guy is showing zero interest in you, it's because they are not interested. And that's a harsh

reality and it makes me sad, but it's the truth. But I'll tell you this, good, because then we can weed out the ones who are not right for us. So look at it like that. Like, okay, great. Well, then I'm just one step closer to finding a great guy because now I can weed out this dud who is not engaging with me. And I think moving forward, then you can know too. Guys, if they are not keeping the conversation going, if they are not reaching out first ever, if they are not asking you questions about yourself, if they're not asking you out, they're not interested.

And I think there are guys who like to keep some girls just on the hook, because I think guys love to have multiple women in rotation. But if a guy is not actively trying to see you, trying to take you on dates, trying to see you, he's not interested and he just wants a fucking pen pal. And we have to be wary of those guys too.

Guys will want to see you if they're interested in you and they will ask you questions. I actually think guys are kind of simple in that sense. Okay, I am going to stop here and we will do a part two because we still have a lot of good stuff to go and we will kick off the next one with a good old narcissist. Always a fun conversation. So I will see you guys next week for part two. And again, thank you for submitting these questions.

All right, have a good week. I'll see you soon.