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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.
Hello. Hello. How is everybody doing?
I just got back from la. It's nice to be back at my house in my own studio. But I recorded some really fun guest episodes last week that are going to start rolling out. So I'm excited for you guys to hear those. Really fun. And I had my 20 year high school reunion which was a blast. I had such a good time. It was so much fun seeing everybody. So a really great trip and now I'm home and I don't have any other trips planned for the foreseeable future. And that makes me a very happy because I just, just want to be home. I'm in this mode of just wanting to be nestling at home. So today is going to be fun because we're doing dating advice which we have not done in a minute. I honestly don't remember the last time that I had you guys submit your dating scenarios and we talk about them and they're always really fun. It's always wild to see the shenanigans you guys are getting yourselves into. So when I was going over these, I was thinking this reminds me of like Sex in the City. You know, we're like getting together with all of your girlfriends. You guys go to dinner and you're all sharing your dating stories and it's kind of mind blowing some of the things that us women go through. So I felt like, because this was sort of like cocktails with girlfriends, I am going to pour myself a little cocktail. So I talked to you guys about them a few weeks ago, but I have the new Kahlua Duncan Collab Kahlua, obviously a brand we all know and love. They are famous for their espresso martinis, which yes, I am healthy and yes, I'm conscious of what I'm putting in my body and I'm also conscious of how much alcohol I consume. However, your girl loves an espresso martini. When I drink, that is typically my go to. But this drink, this new partnership is so, so good, you guys. It is their caramel swirl cream liqueur.
So this is featuring one of Duncan's best selling flavor swirls. The Kahlua Dunkin Caramel Swirl blends luscious caramel and coffee flavor into one easy to enjoy sip. It's made with Real coffee, real cream, and the real Dunkin Swirl flavor. This ready to pour liqueur is creamy, irresistibly smooth, and perfectly sippable. And that. It really is. It is so good. It is such a treat. So I'm gonna pour 2 ounces in a cup if I can get this open. Okay. I'm gonna pour 2 ounces. I'm gonna do it on camera so you guys can see. I don't have the right setup for bartending on the podcast, but. Okay, here we go. You can pour it over ice. You can just serve it chilled. I like to chill. I've chilled my little glass, and then this is also chilled. And I find that it's perfect, but it really. It really is so tasty. Now that we have our little cocktail here, Cocktails with girlfriends, and I will put it right here. Well, cheers. Before we started, I was thinking it'd be kind of fun to play some sort of a drinking game. Like, every time I say some sort of a word like sex or something that everyone has to drink, but I don't know. I didn't go through them enough to come up with a word. So, anyway, so just make yourself a little cocktail for this podcast and join me, and we can sip on this together. And so quickly to make this creamy, dreamy drink at home, you can do whatever your little heart desires. Caramel over top, I think, would be really good. I mean, you could toast a marshmallow. I mean, like, truly, you guys are probably better at making fun cocktails than me, so the options are endless. But it is so good. You guys can find the Kahlua Dunkin Caramel Swirl at retailers nationwide, including Walmart, Total Wine, Kroger. You must be 21 or older to drink, and please drink responsibly. For additional information, you can visit kahlua.com and you can follow Kahlua on Instagram. All right, let's get into it. I'm gonna see if we can bang this out in one episode, but it may end up being two. When I asked my Instagram followers to submit dating scenarios, it's kind of wild how many people submit things. And I will go through and I'll just screenshot the ones that kind of jump out at me, but there's so many that it's. It's hard to narrow down. But also, it's just, ah, I don't know, it's tough. So anyways, I have a lot. We're gonna see what we can get to. And this is in no particular order, so everyone always Asks to keep themselves anonymous also, by the way. So I will not be saying anyone's names. Okay? Men who say they want to commit then default to just having sex. So here's my take on this. So I think a lot of times, well, there's two parts to this. Men will and say and do anything to get in your pants. Let's just establish that, ladies, okay? Men, their goal is to get in your pants. They have two brains, a big one and a little one. And unfortunately, the little one, I think, leads the way sometimes and surpasses the big one. And they think with their penises, you guys, like, they just do. They have crazy testosterone that runs the show for them. So, you know, just keep that in mind when you're getting to know someone. I also think what happens in dating is, let's say you go on a first date with someone and that conversation of, what are you looking for? Comes up, and the guy is like, I want to be in a committed relationship, a committed, loving relationship. And then he gets to know you a little bit better, and he actually doesn't see a future with you. He realizes that because, you know, they say men have three buckets. There's the dating bucket, there's the sex bucket, and there's the friend bucket. And once you're kind of put in one, it's really hard to shift and get into another one. And they can figure it out pretty quickly. But my guess is what happened was.
That'S probably true. He probably does want to be in a committed relationship. And then he gets to know you, and he, for whatever reason, and I never take this stuff personally, you guys. When someone is not into you, but for whatever reason, he doesn't see a future with you, but he would still like to have sex with you. Because a lot of men don't need an emotional connection the same way that we women do to sleep with you. And so, yes, now he would like to just have sex because he no longer sees a future with you. It's kind of that simple. I think men are pretty simple. And that's not a knock on men. I actually think it's a good thing. But I think us women sometimes want to overcomplicate things because we are more emotional beings, and I think we think about things more than men. Again, that's not a knock on men. I love men. I love men. And I think the simplicity to them is actually quite beautiful. But, like, I always resort back to the fact that you will know if he likes you and wants to have a future with you men make it very apparent. If you're confused, it's because he does not like you. I'm sorry if this is harsh. Okay? He will ask to hang out and plan dates, but he also goes a whole week without reaching out. Okay. I love this one so much. This does not make me nervous. This, to me, is not an indication of how much he likes you. So.
If he is consistently making plans, wanting to hang out, if you are seeing him on a semi regular basis, you're fine. I have gotten to a place where. Well, I'll use. Okay, this guy in LA that I am dating, he's in la, I'm in Nashville. And he's busy. I'm busy. We do not have really a texting relationship. There is a text once in a blue moon and there'll be a little back and forth, but not much. And what he will do is he will call me, but it's not all the time. It's. It just depends. Sometimes it's every few days. But there's been a week where I won't hear from him. And by the way, I'm not reaching out to him either because life is busy. And I think we want to date someone who has something going on, who, who is busy, where they actually can't text you all day and they can't call you every day. And I just think, especially if you have kids, it's busy. Like, I can't talk. I can't. I can't talk to someone all day. And there's been a real shift for me where before, if I wasn't hearing from someone consistently, it would really. I guess trigger is the right word. It would trigger my old wounds, my old patterns, and I'd get really kind of. I would think that they didn't like me. And since I feel like I've really kind of healed myself well, it's twofold. I've been attracting different types of men into my life who are busy and have a lot going on. So they also cannot be texting all day. But I also, I. I like it now. I really like it if someone is blowing me up constantly. It actually drives me crazy to be me. It feels needy. And I also am so busy that, I don't know, I just. I've gotten to a really secure place because also the energy needs to be. If they're not into you, then cool. Bye. Like, I think it's. I understand in the early days you get really excited about someone. It's almost like a little obsessive. And it's Like a dopamine hit every time they text you and every time you're talking to them. But I'm kind of like over that phase, and I've moved into this phase of. Like, I've moved into this phase of. I like when I hear from this guy, but I'm not thinking about him all day long, which I don't. I don't know exactly what that means. But my point is, I think it's okay for people to be living their lives and for you not to hear from him for a week. I guess I would ask where you are in your quote unquote relationship. I think if you guys are semi serious, that's a little bizarre. I think in the early days, though, it's totally okay. And I think. I just don't think that should be a deal breaker. And then if it does drive you crazy, the more serious you guys get, I think it could be a conversation. Because I think when you're in a relationship, a week is obviously a very long time. But I think in those, I think in the first couple of months, if you're not moving super fast, I think it's okay. Again, if everyone is busy, I think it's okay. If he's, like, sitting at home all day, that's a different story. All right. The confusion when you think you're being pursued, then they go cold. This is similar to the first one about wanting a commitment and then it turning into just sex. I think men are primal beings and they pursue and go after what they want until they realize, I actually don't want you anymore. Again, I don't think anyone should take this stuff personally. How I look at dating is if someone doesn't like you or if you're not into someone, that just means you're one step closer to finding your person. So I actually think this is a good thing. I can't remember where I saw this. I don't know if it was a podcast clip or something on social media, but it was saying these people were saying, if you knew, let's say that after 20 people, 20 dates, meeting 20 people or 20 dates, you are going to meet your person, then you would just be moving through these people. It'd be like, perfect onto the next. And now we're one step closer to meeting our man. And so I look at this as a good thing. I think that if someone goes cold, fine, that's not your person, and you don't want to be with someone who doesn't feel the same way about you. So thank you. Now I'm one step closer to finding my actual person. So don't look at this as a negative. And while yes, it kind of can sting, I understand that if someone's like really coming on strong and then they pull back, it's okay. They just realized maybe there was something about you that they didn't see long term or they met someone else. I usually lean on the fact that they met someone else. And that's okay because again, you don't want someone who's gonna be able to jump ship that easily. Guy I'm dating is wonderful, but the attraction just isn't there. I miss the sparks and butterflies. Of course, in the beginning, the sparks and the butterflies are very fun. Anyone you talk to says that falling in love is. It is the most fun. It is, but that will subside, that fades. And I think there's a difference between.
The guy I'm dating is wonderful, but the attraction just isn't there.
Attraction is huge. And I'm gonna be honest with you guys. I think attraction is more than half. And attraction, I think, is the hardest piece of the puzzle. It is so rare, so rare that I'm attracted to someone. So when I am, I get really excited about it. But I think that. I think attraction has to be there. I think there has to be that attraction. There has to be that. Because especially after that honeymoon phase fades away and the butterflies and the sparks do kind of simmer, you have to have that level of attraction still. Otherwise, I just think, I just think attraction, you have to have attraction. And similar to what I said before in that it's okay, it's okay. Because again, if you can move through this relationship, then you're that much closer to finding your perfect person. And when I say perfect, no perfect person exists. But I mean, what's perfect for you? And like, I know that with my own experience, attraction has been so hard to find. And.
I think it's because sometimes if you're having a really hard time finding someone that you're attracted to, it's okay to take a break, to not go on dates, to get really comfortable being alone, to work on self love, to take that as an opportunity to maybe do some extra work at work, like just take it as an opportunity to better yourself, whatever that looks like for you, instead of putting that time and attention into dating and into men. Because sometimes I think it's really good for us to be alone. And I think the universe works in magical ways where when you do need to be alone, it will force you to be alone. And so I never think you should force a relationship. You can't fake attraction. You can't force that. And I think it's okay for this person not to be the one. And I think it's okay to break up with people. And I think sometimes we're in relationships for a short period or maybe a long period, but it's not forever and that's okay. That's all that they were supposed to be in our lives, you know, for that season. And there's growth there and there's takeaway from every relationship. And if you can look at it like that, it's okay that it's gonna end and you will be that much closer to finding your person.
I always get excited to talk to you guys about Shopify because I've been using them since, since I launched Uncommon James. And so if you are like me and have launched your own business or maybe you're even just thinking about it, well then, you know, starting your business can definitely be intimidating and it can be lonely thanks to all of the hats that you suddenly have to wear. I know that when I launched Uncommon James, it was all consuming, it was overwhelming. And you do you have a hand in every facet of the company, which I actually do love that I can say that. But I can tell you I am so happy I had Shopify as a partner when I started.
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All right, let's chat about Skims, specifically about their pajamas. I'm all about being as cozy as possible while sleeping. I feel like I sleep better when I feel good in the fabrics that I'm wearing. And at this point in my life, getting really good quality sleep is the most important thing. Well, Skims has incredible pajamas, guys. I just got a really cute little sleep set from Skims and not only is it really cute and it's nice to wear around the house, but the fabric really is so comfortable and it's almost like you're wearing nothing. Also, they have the cutest holiday pajamas too. So if you're looking for the whole family or just yourself, definitely go check that out as well. I I still will get the whole fam really cute holiday pajamas so you can shop my favorite pajamas@skims.com and after you place your order, be sure to let them know that I sent you guys Select Podcast in the survey and be sure to select let's Be Honest in the drop down menu that follows. And if you're looking for the perfect gifts for everyone on your list, the Skims Holiday Shop is also now open@skims.com All right, let's take a second to talk about Monarch. Well, we all know how stressful the holiday season can be. Between travel, gifts, hosting, entertaining, I mean, you name it, it's easy to lose sight of your money and financial responsibility this time of year. If you want to keep your finances under control this holiday season, you need to be using Monarch, rated Wall Street Journal's Best Budgeting App of 2025. Monarch is the all in one personal finance tool that brings your entire financial life together in one clean interface on on your laptop or your phone. And right now, just for my listeners, Monarch is offering 50% off your first year. Monarch is so great because I love having everything in one place and being able to just track it so you always know what's going on. It's so easy to blow through your holiday budget unless you have a central place to track everything in real time. It's also my essential year end financial reset tool so you can link Everything from investments, 401ks property value to get your true net worth and stay on top of year end priorities like maxing out your contributions to your 401k or your Roth IRA before the deadline. It's so great because you can easily keep track of your finances and my year end financial to do list with Monarch, which means that I can relax and enjoy the holidays. So don't let financial opportunities slip through the cracks. Use code honest@monarch.com in your browser for half off your first year. That's 5050 off your first year@monarch.com with code honest.
All right, shifting gears. Is it okay to date two people at once if you've already told one of them you aren't seeing anyone else?
No, you Just. You're lying.
No, you can't lie. Is it okay to date two people at once? Yes. Is it okay to lie about it? No. So the problem for you is that you already lied and told someone that you're not seeing anybody else. So that's the problem. So I would recommend you have to tell this person you lied, and you have to just own it, and you have to just be like, I need to tell you something. I'm really sorry, but I want you to know that I lied to you about seeing other people, and I am, in fact, seeing someone else. And. And I understand that that may be a deal breaker for you. I'm just trying to date to find exactly what I'm looking for, and this is part of my process. And then you see how he reacts. But he's probably not gonna be too thrilled because you did lie. However, I think you owning it and telling him and coming to him and getting ahead of it is so much better than him finding out through stuff. Stacy that works down at the local bar. Stacy. Stacy, the bartender from the Hills. Name just popped in my head. So I think. I think lying is one of the worst things. And I also hate lying because just personally, I think it's really hard to keep up with all of your lies. That's, like, for me, that's reason enough not to do it. It's too hard for me. I don't agree with this. And especially if you're sleeping with them, I think that just gets really sticky because also, would you feel if he was doing this to you, you would not be happy. So I. I don't. I don't think that's okay. I just have to be completely honest with that. I'm 37, a single mom, and I prefer young guys. All they say is that they can't commit, though.
Listen, I will never judge you for dating younger. I guess I would want to know.
What is it about the younger guys that you like? I would also say if everyone in your life, what doesn't actually matter, the age, is saying they can't commit, I think that starts with you. I think, because, you know, whatever we attract into our lives is because it's whatever we're putting out subconsciously. So I would argue that there's something going on with you that is attracting emotionally unavailable men or women slash men that can't commit. I would also want to know if that's. Why are you intentionally going for younger men because you kind of know that they won't commit. Like, they're kind of Just looking for a good time. And by the way, I don't think this with every young man. I mean, I'm a good example of that. I think a lot of young men would settle down with an older mom. Like I, that was my experience. Like I just do. I don't think that that's completely, completely off the table. But I do think it's probably a little bit harder to find those rare breed young men who are willing to become a stepdad at a young age. But I think this starts with you. So I would suggest doing some inner work, figuring out why you're maybe afraid of real intimacy, why maybe you're a little emotionally unavailable. I would start digging because if you have a pattern, it starts with you. And the universe will keep giving you the same lesson over and over and over until you learn from it. So I think there's really something for you to learn here and to take away.
His teenage daughters are extremely rude to me. It doesn't bother him. He said deal with it. Wow, what a fucker. This is so unacceptable and not okay. It's not even funny. First of all, the fact that this is how he speaks to you. He says it, he's fine with it. Deal with it. That alone, Come on. I don't care what we're talking about. And his teenage daughters being rude to you is pretty bad. But even if it was something small and he said I don't care, Deal with it. Nope. I'm sorry, this guy doesn't sound like a good guy. And especially teenage daughters being rude to their stepmom. Listen, I was a teenage daughter with a young stepmom at one point in time. And it was not an easy situation, probably for both of us. I think that's probably fair to say. But I.
I was never rude to my stepmom until my senior year. And there were some choice words. But my stepmom was also a nightmare. Okay? And my, my dad actually did nothing about that either. So it's kind of interesting. But, but I look back on that and that was extremely toxic. The whole situation was toxic. My dad was toxic. My stepmom was toxic. I was getting into a lot of trouble because I was lost. I had no idea what was going on. And so this just sounds really toxic to me. And so I would ask you, is that the kind of relationship that you want to be in? I would like, to me, this guy doesn't sound like a good guy. And I, I would question your selfworth. Cuz everything comes back to selfworth. You guys what we allow depends on how much we respect and love ourselves. And this, to me, sounds like the bar is pretty low if I'm being completely honest. So I would say, why don't we start doing some work on ourselves to really love and respect ourselves and then this kind of behavior would not fly. It would not fly. And you got to be a tough cookie man to deal with teenage stepdaughters, that is for damn sure. And that's why you really need your husband to be on your side. Or. I don't know. I don't. Maybe it's not your husband, but you really need your man to be on your side for that stuff because that will be. Buckle up. All right. Had a D bag send me a pic of his boxer briefs I will be wearing tonight for the first date. So this guy, before their first date, sent her a picture of his boxer brief saying that's what he's going to be wearing tonight. I really hope you did not go on this date. I really. Unless you're just looking for sex, if all you care about is sex, then have at it. But if you are looking for a committed partner, this is not how you start. This is not how you start. This guy is looking for one thing and one thing only. This guy sounds like a complete fucking douche. Like, I. In what world are we living in that that is acceptable? I wish there was a follow up where I could like call this person and be like, so what happened? Well, should have responded. I should have responded to some on Instagram. I wish I did because that's ridiculous. That's what you. What I would do in that. Sit. I mean, well, what I would do. That's a situation where you can definitely go ghost or you can respond and be like, you know what? Actually, change of plans. I'm not going to be going out with you tonight. This is not how. This is not how I would ever start a first date or something. Or just be. That's a situation where you could be a complete asshole back to him if you really wanted to be, I feel like. Because that's ridiculous.
So I really hope you did not go. Ladies, we are not going on dates with men who send their fucking underwear picture before a first date. No, that's not happening.
Unless you want sex. Okay, I get the ick quick. I also feel I've gotten too content being single. Girl, I feel you. I get the ick so easily over some of the dumbest shit I got the ick over. Our Guys laugh. Guys laugh. Well, that's kind of legit, actually, but. And I feel you, I'm being too content single. But here's what I always say is when the right guy comes along, a, you won't get the ick and B, you're going to be okay not being single anymore. I just really resort back to that. And I know, listen, I've been single for almost six years. Six years. And it would be really nice to be in a relationship and have someone. But you know what? I love myself too much and I value my piece and I love my home and I love my own company that I would never settle for just anybody. And that's how everyone should be. Everyone should be where you're at, where I'm at in the dating world so that you don't just need a warm body next to you so you don't settle and so you don't put up with some of this behavior that we're talking about. So I don't think it's a bad thing that you're too content being single. I getting the ick quickly is not a bad thing. I don't think it's a bad thing. I think, you know what, ladies, we've got high standards. The bar's up here now. And God damn it, the bar was really low for a really long time. So yes, this is a good thing. Stay there until the right man comes. Because when the right man comes, it's going to be effortless. You're not going to question it and you're not going to be writing me on Instagram going, you're just going to know. You're going to know and it's going to be easy. In a seven year relationship and now have a six month old boyfriend hasn't proposed. Do I give ultimatum? No, you never give an ultimatum. Because why would you want to be with someone who isn't 100% truly sure about you ladies?
We want men who are so in love with us, so obsessed with us, would do anything for us, would fucking kiss the ground we walk on. We want men who there's no question in their minds that we are the one. We are the one. There's not. Not a doubt. You don't want to have to give a man an ultimatum ever. You guys, that's not a man that wants to then fully be with you. And listen, if this doesn't work out, then it doesn't work out. I mean, you guys have been together for seven years. My guess is, I don't know, it might not be coming. I think there's always Probably a little bit more to these stories, which is kind of the hard part with doing this. Like, did you guys say in the beginning you didn't want to get married? Has he said that he doesn't believe in marriage? Like, I know there's always more depth to these, but I think like just looking at this, you know, from a long lens is a seven year relationship. You guys have a six month old seven years in. To me, it kind of sounds like this is trying to. This baby's trying to bring you guys closer together, trying to mend this relationship in some way, which I can tell you right now, babies do not do that. Babies never help a relationship. They just make it harder. And if you're feeling like you have to give them an ultimatum, I just think this is bad news. And listen, again, I don't think we should be so afraid of things ending. I think those big moments in life, a relationship ending, a divorce, losing a job, whatever it is, those can actually be the best gift. Because that moment is the turning point then where your life gets better. When you can get through that and get to the other side, that's where the magic happens. You will meet someone amazing. If this relationship does not work out, because again, it's you guys, it always goes back to the self worth. Why would you want to give a guy an ultimatum? You need to love yourself so much that you are like, if you don't see how amazing I am, then goodbye. I will go find someone who values me and appreciates me and who loves my baby. Because you will find.
Explain something. You guys, I had someone tell me at one point in time that meeting someone with kids would be a deal breaker for them. And they never like, oh, a woman with kids. Gross. Someone literally told me that. Okay, if you are reading between the lines and let me explain something to you. Men do not care about women with kids. I'm gonna say it again. Men. Men. Maybe some boys care. Men do not care. If you have kids. I can promise you. Promise, promise, promise you. So if you are listening and you have kids and you're scared to get a divorce or leave a relationship because you're a mom, get that out of your head. Men do not care. And if we turn this into a clip and we post this and some douchebag men on Instagram are like, I would never date a. He's a little fucking boy. That's a little boy. Men don't care.
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I have a crush on a guy in the friend group. What do I do? This is fun. I love this. Okay, you have a crush on a friend in the. In the group. Okay? So here's what I would do. I would just start flirting and being a little more touchy feely. Make it more of a point to be next to him to just. I would just get the flirtation going. Okay. And.
I think.
I think guys can usually pick up on that. I would amp up the flirting. And then after doing that for a couple of weeks, depending on how many times you guys see each other, but after doing that a few times, right then I think you could definitely slip into conversation when the time is right, when the moment is right. You could start it as sort of a joke and be like, have you ever thought about us dating? Or like, like, oh, you know, you could do action. You could be like, I had a dream about you and in my dream we were dating. Like, you could do something kind of silly like that if you don't want to just like, blatantly say, hey, I. All of a sudden I have a crush. I think I have a crush on you. Which, by the way, you could totally do. Like, all of these are great options. I think if you have confidence with it and you just own it and you could do it really playfully, or you could just be like, listen, you know, this is how I'm feeling. You could do it after a couple drinks if you really needed some liquid courage. I'm not encouraging getting drunk and drinking. I'm just saying, like, when you're out at a bar and you're flirting and you're having fun and there's some drinks, I do think it's easier. I do. Or if you guys want to play it a little more serious, call him during the day and just be like, hey, I want to talk to you about something. All of these options you can do. But what I'm saying, what I, what I would do though, is I would first just, like, amp up the flirting. I would touch his shoulder. I would like, brush up next to him. I like, do those things for a minute and see then how he reacts. And if he's still not taking a hint, if he's still not making a move on you, then you could go the other route. And put it more on the table. But I think that's exciting. Hey, listen, if a relationship can start from a friend dynamic, I think that is good gold. I wish I had someone in my life like that. So I love that. Good luck. I think that's very exciting. Can you DM me and let me know how that goes? Okay. We're going to be able to do all these in one podcast, so I'm happy about that too. All right, where do I meet 35 to 45 year old single normal men? I'm tired of the dating apps. Girl, I feel you. God, I feel you. I'm off all the apps. Well, I was only ever on one, but I deleted Raya. So here's what I think. 35 to 45 is a tricky age because I have found, I think more divorce happen closer to 45.
There. 35 is tough. So. But. But they exist. They're out there. I think you have to start saying yes to more things. And I've been doing that as well. I think it's being a little more social, going to different places than you would normally go to. Trying a new restaurant, trying a cool new bar that you've heard of. Maybe a bar at a new restaurant. The golf range. So I have been golfing with Camden a lot and I'm with my 13 year old son. So it's not like I'm like, hey, like flirting with guys. But there are men at the driving range, at the golf course. If you can get to a golf course, that is a, that is a great place to be for men. It is all men at those places. If you can find tennis, indoor tennis, if you can find someone, because we. I've talked about this on the podcast before. I've had a lot of people say, Home Depot, go to Home Depot. That's a little bit harder to like strike up a conversation with someone and meet them. But I think it's just about going to places you wouldn't normally go to. Trying a new coffee shop. I think, honestly, you guys, I see really cute people at Whole Foods all the time. It's just putting yourself out into the world more with the energy of warmth and an inviting, an inviting energy. I think if you're going out into the world and you've got a hat on and you're really keeping to yourself, you're not looking up well, no one's going to approach you. You have to be. You have to keep your head up high, put in maybe a little bit more effort into your appearance. I am guilty of This I am usually out and about. My hair is greasy, I'm in leggings with no makeup. And I think, you know, lately I've just been actually washing my hair and making my hair look good. What do you know? So I think it's just putting in that effort, maybe wearing jeans instead of leggings and just putting yourself out into the world. But again, I think that's a, that's a tough age range. I think you're going to have more of a realistic chance of meeting men 45 to 50. Just saying. Also, get friends of friends. Like get groups of people together that you wouldn't normally get together. Like everyone. Like maybe all of your friends. Invite some one of their friends that you don't know. You know, like that, that kind of thing. You just have to get creative. But by the way, I always will resort back to the fact that when it's supposed to happen, it will. And if you're in a phase of being alone, lean into that. I really think it's there for a reason. I really do. All right. Every guy I've been interested in is never emotionally available. It's been 10 plus years of this. Similar to this single mom that's dating these younger guys. This is about you. This is about you. Everything you're attracting into your life starts with you. So I would dig deep. I would go back to childhood. I would go back to your relationship with your dad. I would go back to past relationships. If there's some sort of trauma there, there's something going on from your childhood though. So we got to get to the bottom of that and we have to heal that and then there will be a shift. And guys, I know that I preach this, but I am a great example of this because I had a lot of trauma, specifically with men, and I was attracting really not great people into my life. And since I've done the healing work, you guys, the guys I'm attracting into my life are great now and. Yeah, well, I haven't met my man, you know, my forever. But I know he's coming because every, all of the guys I've gone out with in the last however many months, they're different. There's been a shift. They're really good guys. Like really good guys. And that was never the case for me. So it starts with us. Starts with you, baby. Gotta get in there. You gotta dig deep.
Okay. We love this conversation. When to sleep with the guy. I feel like I always do it too soon and it changes the dynamic. So here is the deal. I've said it before, I'm going to say it again. I don't think it actually matters when you sleep with a guy. Fucking sue me. It doesn't. And here's why. I'm going to tell you why. Because if there is real chemistry there, real attraction, if there is some sort of a soul connection, you could sleep with him in the first two minutes and it wouldn't matter. If a guy likes you, he likes you and has nothing to do with when you sleep with him. However, if a guy doesn't like you and you sleep with him immediately, yeah. He's not going to keep chasing you and put in the effort because he already got what he wanted. So I would say in the early dating phase, I am not one to say sleep with him on the first date. I actually don't think that you should. However, if you do, I'm not going to judge you. And again, I resort back to if he likes you, it doesn't matter. I will always take that stance. But my advice to you would be definitely make him wait a few dates. So I think if a guy just wants sex and you hold out for, let's, let's say you hold out for a month. If a guy is only in it for sex, he's going to drop off naturally. So, you know, if you're worried about this, make him wait. I think you should wait a little bit longer then. And.
Especially if you sleep with them and then it changes the dynamic because guys are hunters. They want to go after what they want. And so even if it is just sex, there's still that little bit of chase and there's a little bit of thrill in it. And so I would definitely say if you're sleeping with them too soon, make them wait a month at least. And guys, I will go back to listen, if you only care about sex, it doesn't matter, then have sex with him, you know, or.
I just think it, I just think it really depends on what you want as well. I don't think we should always be putting everything up to the guy. Why are we always leaving this stuff up to the guy? It's also, what do you want? What do you want? But yeah, I mean, I definitely, I definitely think, I think, you know, because you're saying you always do it too soon, so then, you know, that's your answer. What do you think about situation ships since dating is so hard to find my person. Oh, I actually didn't know that was the next one. But that actually goes very well with what we were Just saying, it's whatever you want. If you want a situationship, if you want to have sex, then by all means have had it. I think you should. I think it's empowering for women to be able to decide these things as well. It shouldn't always be up to the man. So I think there's nothing wrong with the situationship while you're waiting for Mr. Right, if it works for you. I think if your situationship is taking up a lot of your time and your energy, maybe that's not a good move for you. If you're wanting to be in a committed relationship, then I would say maybe end it. It depends on, depends on your emotional capacity for it, I think. And as women, we unfortunately do become more attached. I know I can't sleep with someone unless I have an emotional connection. And so it's harder, I think, for women to have a situationship. That's just sort of the nature of the beast. So much easier for men to sleep with a woman and not really affect their day to day. So I think it depends on what you can handle. But I think there's nothing wrong with having some needs, you know, wanting your needs to be met while you're waiting to find your person. Oh, I love this one. The more I improve myself, the harder it is to find men because they're not on my level. This is what all of us women should strive for. You guys, that the pool has now become so small because we're so healed that it is slim pickings out there. And yes, it's harder to find someone, but when you do find someone, they're going to be amazing and you're going to go, this is why I didn't settle. And I'm so thankful. And someone who gets you on every level and it's going to be magic. And that's what I'm waiting for. And yeah, it is really hard to find someone because when you, when you work on yourself and you do all of the things to be the best version of yourself, it's really hard to find people who are on that level and can, who can see eye and eye to eye with you, but they're out there and that's why it may take a little bit longer. And you have to just stay strong and stay content in your peace and your energy and, and lean on friends for the fun and keep improving on yourself because nothing bad is gonna come out of that. And again, we attract what we are. So if you are whole and healed and radiating from a place of love, you Will attract it. And it may take longer to sift through some of these people. But he's coming. He is coming. Any compliment a guy gives feels like he's full of shit and just being a player to get what he wants. Again, this is about you. It sounds like there's a real trust issue here, which totally get. And by the way, yes, I said it earlier, guys are going to do and say anything to get in your pants. You're not wrong. But I would say.
If you can't believe anything that a guy is saying to you, I do feel like that's about you. Because I think a guy can tell you you're beautiful and also want to get in your pants, but still think you're beautiful. I think both things can be true. So I don't. I don't think guys are going to lay it on so thick if they're completely full of shit. I think this starts with you. Why can you not trust guys? What is this about again? Let's go back to childhood. Let's go back to our relationship with our dad. Let's go back to our relationships with our brothers. Any man who's made a lasting impression on you, I want to know where this comes from. And I think that you've. You also need to do a little digging again, you guys, everything that you're attracting, and if it is a consistent theme, it's the same thing happening over and over. It's. We gotta start asking ourselves why. Why am I attracting this into my life?
All right, and then the last one.
I have fun in the moment, but when I'm not with him, I'm not excited to hear from him.
I get it.
I think it's really easy to be on a date, let's say, and be in the moment and have fun. You know, like, I can have fun with anybody. Pretty much. Like, you could put me at dinner with anybody, and I'm going to enjoy it. I'm going to make the most of it. I'm going to have a great conversation. I'm gonna. I'm gonna have a good time. I really do think it's how we feel after a date or the in between. If you're really not excited to hear from this person, chances are this is not your person. And I think maybe you're similar to me and that you could probably talk to a wall. You could probably have a good time with anybody. And that should not be mistaken with chemistry and attraction. I think. I think that in between is actually how we know. And especially right after A date. How do you feel post date? Like, in that moment, is your energy drained? Are you exhausted? Are you tired? Or are you energized? And are you like, wow, that was really fun? Are you thinking about him the next morning? Do you get excited if he texts you after the date? Like, that was really fun? Or if not, I think that that's your answer. I think that's your answer. And again, guys, let's not. Let's not get down on ourselves about ending something, because when you end something, it creates space for something new to come in and someone better. That's been my experience. You end one thing, something else comes in shortly thereafter, and it's better. And they keep getting better and better and better. And you have to keep working on yourself in the meantime as well to make sure that they keep getting better and better. But I love doing these. These are really fun, and I appreciate you guys being vulnerable and putting this stuff out there, because, listen, the dating world is not easy. You guys know, I've had my fair share of bullshit. And listen, I've been single for six. Almost six years, guys, okay? It. And I. That's a long time. That is. That's a long time. Sure, I've dated here and there, but I've been single. And.
I think, you know, like, when you hear about people post divorce, like, they were single for two, three years, like, I've been single for a while, but I hope I can be inspiration for you guys, that it's really okay being alone and being single. And I can't wait until I do meet my man, because then I can be like, see, look, I told you. And he's gonna be amazing. And then hopefully I really will be an inspiration for you. But I think the focus should be working on ourselves. Being okay being alone, being okay ending a relationship, knowing it's this or something better. It's all happening for a reason. What's the lesson in this? I think those are the things we need to start wrapping our mind around. All right, thank you, you guys. I will see you next week.
Yeah, I got all the power. Please note that 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.
Episode: Taking Our Power Back In The Dating Game
Date: December 9, 2025
Host: Kristin Cavallari
Platform: Dear Media
In this episode, Kristin Cavallari dives into real talk about navigating the modern dating world, sharing unfiltered advice and answering listener-submitted dating scenarios. She explores self-worth, emotional availability, communication, red flags, attraction, and empowering yourself while single, all through her signature blend of honesty, humor, and a bit of tough love. Kristin’s guiding theme: taking ownership, knowing your worth, and unapologetically raising your standards.
Kristin is candid, chatty, and direct, mixing humor, tough love, and empathy. She regularly returns to the importance of self-worth and encourages using singlehood as a time for self-growth, not just as waiting for “the one.” The language is informal, sometimes explicit, and always honest.
Kristin’s central message is about “taking your power back” in dating: own your choices, don’t settle, set high standards, do the self-work, and trust that love comes from a place of self-contentment, not desperation.
For more advice, follow Kristin’s podcast for upcoming guest episodes and dating deep-dives.