Date If You Dare


Hosted by Colin Hodge, Annie Chen & Stella, 'Date If You Dare' welcomes a new guest every week to share tips when dating, experiences about sex on the first date, hookup dating sites, threesome sex…and more crazy stories. You might get inspired by some of the dating advices on how to get laid… or how to not get laid. Who knows?


Available on

Apple Podcasts
Google Podcasts

Listen Now!

Michael: Brought to you by Down Hook Up and Dating app. Go to the iOS App Store and download it now.
Jack: My craziest hook up story in one word would be best 'laid' over ever.
Colin: How many words is that?
Michael: *laughs* Did you get it wrong on purpose?
Jack: It's hyphenated, okay? Hyphenated.
Michael: You said laid again.
Jack: Oh, I thought we were going with that.
Michael: No, We're not. Anyway, go ahead.
Jack: Okay. No shit, there I was. Everybody's been there. Everybody's been traveling on holidays. And you guys already know how much it sucks, right? So there's no shit there. I was going home for a holiday and then I was flying through the Midwest because I went to school on the East Coast. But there's just the biggest snowstorm in apparently what they said was a decade hit and we were stranded. So our plane landed late and there was no plane going out. And everything in the airport, in the lounge, and all the other cafeteria and staff had already been let out.
Colin: Snowmageddon.
Jack: Snowmageddon for sure. I felt like it was 2012 in real life. And the funny part was it was 2012. I wasn't paid to be a part of that movie, so we're not going to advertise that. So me and my buddy were like, all right, well, what are we going to do now? There's really nothing else for us to do. So we're stuck in the airport due to inclement weather. We just like, all right, well, might as well just find a place to camp out and chill. I was walking around the terminal looking for a john because I really had to go. And I really hate airplane trains.
Michael: Oh my god.
But anyways, I see this freaking hot girl like head across the board. I think Kate Upton coupled with Eva Longoria and then Kate Middleton. Just that class is there.
Colin: So we're talking veluptuous.
Jack: I'm talking not lacking in any department. Not lacking any department. Like, I can't- It's just tens, tens across the board. Easily, easily out of my league by miles. But I was just like, oh man, what else am I to do? She's stuck here. I'm stuck here. We're both fishing a barrel. Why don't I shoot my shot? So I go up to her. Just as I was about to get close enough to her, then she just turned away. I was like so I was like, all right, well look, I might find her on social media since everybody stuck to you, right? Pick up my phone. And I started looking on Instagram tag. I was like, seriously looking for this girl.
Jack: And then I was like, oh, I finally see her and then I shoot my shot. I was like, well, what's the worst she's going to say no. And I shoot my shot. Obviously no response. Probably stuck in the request folder. And then I was like, all right. Me and my buddy, we were hungry. We're cold. Somehow heat had gone out in our terminal. So we were like the staff was asking us for I don't know what it was, the airport staff or the airline staff. They're like, ladies and gentlemen, we're going to have to ask you to move.
Jack: And so we're like, this is the worst layover experience ever. So I was like, well, I'm going to pick up. I started browsing all the other apps on my phone. And I was like, oh, might as well see if there's anybody active in this region. So I opened up the dating app and I started swiping. And then my eyes lit up. My friend thought I was having, like a seizure or heart attack or I was going to go to my eyes went like, super wide. And he's like, what? I was like, I found her, the Holy Grail. I found her-
Colin: My precious.
Jack: So I was just like, I'm going to use my good old charm as a keyboard warrior. So I swiped and it was a match. I really literally thought that there would be nobody, nobody swiping in an airport terminal in a snowstorm.
Michael: But if it's a match, that means she matched you before you matched her. She swiped you as well. Love this.
Jack: Exactly. So that's when I knew that this girl definitely down. Definitely down. So I was like, all right, I'm going to shoot my shot. So I come up with my best line. It was some corny crap. Are you a snowflake?
Colin: You can swear on this. Don't worry.
Jack: Really? Okay. Some corny shit. I was like, oh, man. Are you a snowflake that falls for you? And I tried to be funny. I tried to try to match the seasons and make light of our situation, but she wasted no time. She literally was just like, yeah, okay, so what are you up to? Where are you at? I was like, oh, like, where am I at now? I'm in terminal 59. What are you talking about? Okay, I-
Michael: Well it wasn't terminal 69.
Jack: So I asked her whether I got you going feeling down too. And she's like, yeah, I'm down if you're down. So we linked up, funny enough, linked up around terminal 62. There was no 69, unfortunately. But we walked around for a little bit trying to find like a quiet spot where there's nobody around. But it's a snowstorm in the Midwest, right? Every terminal is packed with people just trying to find a comfy place to sleep.
Jack: So all the good spots were taken. All the lounges were closed, all the shops were closed. And we were like, shit, what are we going to do? So we walked all the way across the airport to the domestic, to the International Lounge. And then we're like, all right, this seems to work. But we're still out in the open, so we couldn't do anything here. And then she's like, hey, look, that Sky Bridge is still connected. I was like, are you serious? She's like, well, do you see anywhere else with an enclosed space? All right, ma'am, if that is your request, and I'll be obliged.
Michael: I love a girl with a great imagination.
Colin: Yeah.
Jack: I'm obliged to acquiesce your request. So word to the wise, don't ever have sex in an airbridge- in a sky bridge. That thing is not stable. The other end of it is open because there's no plane attached. Drake up. Cold as hell, but, yeah, it was in a closed space.
Colin: You got frostbite on your ass, didn't you?
Jack: But I didn't get frostbite on the other end, so that's what counts.
Colin: I'm sure that was warm.
Annie: Was this friend watching you?
Jack: No, but I got branded with the hose before bros for a good year and a half.
Michael: You got off easy.
Jack: I did.
Colin: That's what she said.
Jack: He told all my friends, like, dude, this guy hoes before bros. But in his defense, I was a straight test across the board, so, I mean, I wear it like a badge of honor. Anyways, after the sky bridge, and by then it was like, I don't know, early in the morning. And then people are starting to filter back in. But our flights still the other connecting plane didn't get here, right? So we could fly out, but the lounges were open, and we're like, all right, well, we might as well get some pancakes. I mean, you already had the cream pie, but you'll get the pancakes to go with it.
Colin: You cooked her some breakfast.
Jack: I did. I was a gentleman. A gentleman and a scholar. So we headed over to lounge, and we noticed, like, hey, they have showers. I mean I feel like after getting dirty, it's symbolic to get clean until she actually is like, wait, why are we getting clean? We're just going to get dirty again. Ho- Hold up. Wait a minute.
Michael: Solving problems in real time. I love it.
Jack: I was just like and she said, modern problems require modern solutions, and they gave you a solution, so we have to create a problem. And again, word to the wise addition b on the B side. If you're going to have sex in a shower, make sure that the walls extend to the bottom of the tiles. It was insanely difficult to find footing, and ultimately, I was able to wedge my heel against that little T barrier and find some leverage. But oh, my gosh. Hardest core workout I've had in a while.
Michael: No pun intended.
Jack: No pun intended. But, yeah, after that, I was just like, oh, okay. So I guess this is where we part ways. And she asked me, Where are you flying to? I was like, I'm flying to Vancouver. And she's like, Oh, I'm flying there, too. So I definitely did not enjoy the Latrine. Same. I still hate it. But this play was a little bit better. I got to renew my Mile high club membership card. Funniest part, I thought like, oh, my gosh, this is amazing. Right? Let's trifecta Lancy and Air. And I was like, Okay, so I'm going to try to get this girl's number or contact info because we're both going to be in town and it's just for the holidays. We both go to school in the East Coast. What's the harm? As soon as we picked up our luggage and we're going through that customs gate, I try to catch up with her and then she suddenly starts bolting. It's like, whoa. I did not expect this until I saw who was at the end of the gangwalk.
Annie: Your friend?
Jack: No. That would have been a crazy turn. But it was her boyfriend.
Michael & Colin laughs but also ooohs.
Annie: What?
Jack: It was her boyfriend at the end of the gang walk with some 'welcome home' sign. I didn't even catch your name until I saw the sign.
Michael: Was he holding cream puffs for-
Jack: *laughs* no, he was holding roses. Also symbolic, but not as symbolic as the job that I pulled.
Colin: Wow. I hope she bought some mouthwash at that airport lounge.
Jack: It came complimentary.
Michael: I think you came complimentary, but I'm not going to go there either.
Jack: I came unprompted. It was probably the best 'laid' over story ever. I've been traveling for a long time and this is my best 'laid' over story ever.
Annie: Wait, did you block her on Instagram and that dating app? A boyfriend doesn't find out and maybe kill you?
Jack: I mean, lady's prerogative. She texted me on social media. I don't think she even checked it. So I feel like I'm in the clear. Right? And hey, no names were exchanged in this whole process. And I only caught her name because I read her boyfriend's handmade poster.
Michael: That is the best.
Jack: But yeah, I feel like if there was a hall of Fame for stuff like this, I definitely have a chance at the title here.
Michael: That's perfect.


The Unforgettable Threesome
Online dating seems very simple. Swipe, get a match, chat, then schedule a date with your dating app matches. What could go wrong? Colin was meeting someone he'd met on one of the famous hookup sites. He was just looking for casual sex, and then... Did he get the hookup sex he was hoping for?
The Murderous First Date Sex
You're at a bar, met some nice ladies, took them back to your apartment. Sounds like the perfect night. What could go wrong? For Michael, that night was definitely unforgettable.                                                                                                                                                                              
Women Dating Advice: How To Run From Your First Date
Crappy first date? Don't worry ladies, we're here to save you! Sara went out with her perfect date, who turned out to be...well, not so perfect. What happened, and how did she manage to run from the romantic first date?
The Holiday Hookup: Casual Sex At The Airport
You're stuck at the airport. There are tons of things you can do. You can sleep, walk around, or...You'd be surprised at what you can do.                                                                                                                                                                              
The Car Shaking Orgasm: Elena Gabrielle's Epileptic Date
When the sweet release comes, everyone shakes a little... but then he shakes.. and shakes.. and keeps shaking.. and then... Oh. My. God.                                                                                                                                                                              
Amelia Jane Hunter's Bloody Piercing Date
Ever heard of the Prince Albert piercing before? Then you know the pleasures and dangers it could bring. Needless to say, Amelia's story was bloody... amazing                                                                                                
The Uninvited Airbnb Host: Jamie Wang Exposed
A trip with an ex already sounds like it could go wrong, but Jamie Wang finds herself in a stickier situation… What exactly happened on this trip??                                                                                                                                                                              
Don't Drink The Cherry Kool-Aid!
Ever had a hookup that went wrong? Well this one definitely went wrong. I wish we were talking about Cherry Kool-aid the drink here, but.. well. Listen for yourself and see if you'd want to have Cherry Kool-aid after this.                                                                                     
Why You Shouldn't Push Her Head Down
When Sophie decided to become a social butterfly in college, it's not really what you'd think would happen…                                                                                                                                                                                                                                                                                 
Want to be a guest on our podcast?
Sign up now!
Fill in the form here and we'll get back to you