4.4 • 21.3K Ratings
🗓️ 28 August 2025
⏱️ 53 minutes
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#871. Did you know Colton Underwood and Kaitlyn are cohosting a brand-new Hulu dating show, Are You My First? Now that the season is out, they can finally spill all the tea — and this is the convo Colton was most nervous for… because when they sit down together, things get way too comfortable ;)
We cover it all — their totally different journeys with love and sex, how Colton finally lost his virginity, and the guilt, confusion, and shame he carried while trying to convince himself he was straight. He opens up about faith, coming out, and what life looks like now — married, starting a family, and finally living as his best self.
But don’t worry, it’s not all serious! They spill behind-the-scenes tea from filming on a tropical island (think lightning strikes & jellyfish attacks), dish on cast secrets, and even debate who was really a virgin. Plus — reunion plans? A lie detector for season 2?
Hit play for laughs, honesty, and stories you won’t hear anywhere else.
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EPISODE HIGHLIGHTS:
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0:00.0 | This episode of Off the Vine is brought to you by Audible. Your first great love story is free when you sign up for a free 30-day trial at audible.com slash vine. |
0:08.4 | Figs, if you're in healthcare or shopping for someone who is, you can get 15% off your first order at wherefigs.com with code Figs RX. |
0:17.4 | Progressive, visit progressive.com to see if you could save on car insurance and Ladyworld. |
0:21.7 | Come join me for a really fun weekend. Get your tickets now at ladyworld.co. I'm also doing a meet and |
0:27.7 | greet. |
0:32.6 | You're listening to Off the Vine with Caitlin Bristow. |
0:37.1 | Hey, Vino's real quick. If you are listening right now, which obviously you are, |
0:41.0 | you wouldn't be hearing this, can you hit the subscribe or follow button on whatever platform |
0:44.9 | you're on? |
0:45.5 | Please, that one simple thing helps more than you even realize it allows me to keep growing |
0:50.5 | on this podcast and making these episodes the best they can possibly be obviously for you. That's the only favorite I'm going to ever ask, okay? It truly means the world to me. Thank you. Now let's get into it. Hey, everybody. Welcome back to Off the Vine. I'm your host, Caitlin Bristow, sitting down with my co-host, Colton Underwood. Isn't that funny? Yeah. You're my co-host in real life. Not of this, but co-host of |
1:12.4 | Are You My First? The co-host of Are You My First, where we assembled 21 of the hottest, |
1:18.3 | horniest versions, and they all, well, some of them found love, some of them found self-love. |
1:24.7 | And some of them found their first. And some of them found their first. So it is streaming now on Hulu. We are very proud of it. It's on Disney Plus for my Canadians out there. It was just like a nice dating. I want to call it experience or experiment because we talk about this a lot. But the fact that they all came in with the same common ground. you know i I think a lot of times that Colton can attest to this, that he was on a show like The Bachelor, where you have to have have a one-on-one date to sit down and talk about being a virgin. Then you watch them shift into like, oh, God, this is a responsibility. It makes it a big thing. Yeah. And people feel a lot of shame around their sexuality. Totally. Yeah. Yeah. So this was like a safe space for them. It was really an important, fun, beautiful journey. Again, it's called Are You My First? And we talk all about that show behind the scenes. And what else do we talk about? Well, fertility. Faith. |
2:18.3 | Toads. |
2:18.4 | Toads. Wiki feet. Free feet. I'm laughing, but we really did. We covered a lot of ground. Yeah, let's just say that. We covered a lot of ground in today's episode and we hope you would do it. Well, this is fun. This is so much fun. I feel like you and I have been doing the rounds for media and |
2:35.3 | to sit here now and talking about it. I'm like, I'm going to ask you the same questions. I know, but I'm the most nervous about this one because we're too comfortable with each other. I'm like, oh gosh, this is going to get. Yeah, it could get weird. It could get messy and weird, but messy and weird. But that's what we do on Off the Vine podcast. It's not a podcast with me if it's not messy and weird. |
2:36.0 | For sure. And you are also. weird but messy and weird but that's what we do on off the vine podcast it's not a podcast with me |
2:51.9 | if it's not messy and weird for sure and you are also by the way i think one of my very first |
2:57.9 | podcasts after my bachelorette season yeah and i remember it was so interesting because obviously |
3:03.8 | you have PR with you from the show so you aren't allowed to say certain things, but I feel like they let you kind of say what you want. Yeah, because they also knew you would, you know, protect a little bit. Yeah, of course. Yeah, of course. I was just doing the Girls Got to Eat podcast. Yeah. And, you know, they're like all about sex and ranch and all this stuff. And I love them. They're so funny. But it really does just bring out this side of me where I'm like, okay, reel it in, Caitlin. I was like talking about my first, of course, because we're here to talk about the show. Are you my first? And they're like, what was your first like? And we've talked about this so many times now in interviews. And I was like telling them how terrible it was. And then they were all like, yeah, our guys first, like, we all had big dicks. And I was like, wait, mine was too. And I was like, it did not tickle. You're like hot. Yeah. And we're all talking about like our first big dick. So funny. Okay. So we'll start with the obvious. Our experiences with love and sex are very different. Are they? Just a little. Just a little. A little bit. |
3:59.0 | So hosting this show together kind of puts that front and center in the best way. Yes. I agree. And I think I mean, like we can talk about it here. But like when we did our chemistry like test together. Yeah. I was like, oh, this is it. Yeah. Like this is it just works. It's yin-yang. It's just this compatibility that was so effortless. Yeah. And that was the other thing, too, is like, as hosted the show, you need somebody you feel comfortable with because if you forget your lines or you needed to say something or like somebody was better suited, we picked each other up really well. We really did. Yeah. Yeah, yeah yeah we did it was so it was so funny because i don't think i realized that i was doing a chemistry test with you like i think i just thought i had the gig and i was just meeting everybody you and that's where we're similar we're both manifesters and we're like i'm gonna walk into this is already my thing yeah and and i I think that's, it's the confidence thing of like, fake it till you make it. |
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