Sex + Dating

Angelenos Share Their Craziest Dating Stories

crazy online dating stories
Jason Hoffman & Daniel Fishel/Thrillist

In a city boasting over 8 million people, many of whom traveled here from all sorts of places with ambitious dreams, you’d think you’d have a decent selection of seemingly good-looking, dateable options. Unfortunately, not every swipe right is a Mr. Right -- which is why we asked a bunch of Angelenos about their craziest dating stories. Grab the popcorn...

This girl got asked out by an actor on the CW and just couldn’t keep her cool...

“This one time I met a guy on Bumble who was an actor on a well-known CW show I used to watch religiously. He suggested we meet at Father’s Office in Santa Monica for some dinner and drinks. I of course played it off like I had never seen the show so he didn't think I was a total fan girl, but after the drinks were flowing, I slipped up and called him by his character's name on accident. He called me out, and needless to say, there was not a second date.”

-- Madison, Santa Monica,  23

This guy’s story will make anyone who’s ever gotten a little too tipsy before a Tinder date feel better...

“Of course, we met on Tinder. We went for tacos, upscale, not some $1-a-pop truck, off the strip in West Hollywood. I was there first, in a good shirt. I saw her smile as she crossed the road -- beautiful tanned skin, a sweet dress, skinny legs and that way of looking ever-so-slightly different to the photos all girls from Tinder have (I don’t mean that in a bad way, but that’s the way it is). 'HI!' she said.

“'That’s loud!!!' I thought, as I embraced her...

“We went inside and she exclaimed loudly at the board. Yep, she was drunk. Everybody in the place turned and stared -- everybody knew we were on a first date, and everybody realized she was drunk.

“Despite struggling with her words it was pleasant, and I figured she’d had some wine because she was nervous, so we went for a drink. She offered me a lift home. I wasn’t sure she should drive, but she insisted. We talked and laughed. We stopped at a light and it was quiet for a moment, almost romantic. She turned and looked at me, lingered for a second, then suddenly turned and went to wind down the window. Didn’t make it and puked all over the window. Turned forward and puked all over the wheel, the dash, herself, the radio and finally me. In the car. The light changed. People started on their horns, so we had to keep driving, covered in puke.”

-- Andy, West Hollywood, 33

This girl’s story is bound to raise some eyebrows at the Uber headquarters...

“We met on Bumble (my dating app of choice). He was a doctor, seemingly good-looking, and appeared to have his shit together before the age of 30. So when he asked me out to EP & LP -- and for dinner nonetheless -- I gladly accepted.  

“I got there early, and he arrived a few minutes after. We made eye contact from across the way -- he was just as cute as his pictures – which doesn’t always happen. He made his way over and embraced me in a warm hug. We ordered a round of drinks, some appetizers, and split an entrée while engaging in your typical, first date, casual conversation, which is when we soon found out we are both 4/20 advocates.

“He then proceeded to tell me about the last time he was in an Uber and how he hit it off really well with his driver who let him in on his side business where he occasionally sells joints to customers. He then proceeded to say that anytime he needed one he should take down his number and call him up. Naturally out of curiosity, I said let’s try it out. He gladly obliged and texted the driver and sure enough within minutes he responded saying he could be over within 20 minutes.

“So we got the check (he paid) and headed out to meet the Uber driver who was there, joint in hand, which he not only sold it to us, but ended up letting us take on a free ride. We spent the next 20-30 minutes joy-riding in and around the Hollywood Hills hearing this guy’s life story about how he met his now-baby mama while driving for Uber.

“Afterwards he dropped us back off at the restaurant, I thanked him, and we hugged goodbye. I heard from him a time or two after, went on another date, but nothing more ever came of it, because nothing ever really does these days.”

-- Rebecca, Mid-Wilshire, 28

This girl had a threesome with a C-List celebrity...

“Without a doubt one of my proudest dating stories involves my best friend and a C-list celebrity. We were at The Den after a drunken Taco Tuesday at Pink Taco, and we were sitting at one of the tables outside wreaking havoc on the place since it was pretty much empty except for our group. At the table next to us, I saw a guy who looked super familiar, so obviously I sat there blatantly staring at him until I realized he was one of the main characters on a really popular HBO show. I've lived in LA my entire life, but I've never been one of those girls who sees celebrities everywhere, so naturally I was freaking out. We eventually get drunk enough to start conversation, with a casually obvious, ‘Hey can we bum a cig’ line even though neither one of us smoke. At first we played it super cool, asking him what he did for a living, ‘Oh my god, you're an actor? That's cool, I don't really watch TV.’ However, then we proceeded to get to a certain level of drunk, at which point we started giving him our unsolicited analyses of how we felt about each season on the show he was in. Finally, we ended up going back to his friend's place, and one thing lead to another, which lead to us having a threesome with a C-list celebrity. 

-- Britney, Hollywood, 22

Let’s hope this guy’s wife isn’t reading this one...

“I found a married man on Tinder. While his profile didn't outright admit his married status, it did link to his Instagram account where the picture of his wife and him on their wedding day had warranted quite the impressive amount of likes. Since I had about as much shame as Paris Hilton in the early 2000s, I swiped right and lucky me, we matched. What surprised me more was after a couple hours later he messaged me and we began to chat. We conversed over Tinder for a bit, but then things got ‘serious’ and we quickly moved to texting. He would half ask me out for a drink and I would half inquire about his wife (apparently it was an open relationship where either could sleep with other people). However, I got the feeling that the door was more open to one of them than the other, but who was I to judge? My curiosity was waning since this really seemed to be going nowhere until one night at about 3am, he texted to see if he could come over. I had never had anyone come over without getting at least a drink first, but I couldn't help myself, so I said ‘sure.’ We sat on my porch steps and drank wine and chatted until I deemed it safe enough to let him into the house. We started making out but a giant red flag popped up when he said, ‘I can't believe this is happening.’ I asked again if his wife would be okay with this, to which he gave a clear affirmative. I'll sleep with a married man, but home wrecker I am not. Things started getting hot and heavy when I realized there wasn't a condom in the whole of my house. Married Man said he would leave and go get some... and HE NEVER CAME BACK. He texted me the next day to say that his phone had died on the way back and he couldn't remember which house was mine but my suspicions arose when he deleted his Tinder the following day. Seemed to me like the Married Man wasn't ready to venture all the way out of his open door policy. 

-- Libby, Valley Village, 29

la's craziest dating stories
Daniel Fishel/Thrillist

This guy almost had a date with Robert Pattinson’s sidepiece...

“One evening I was just hanging in my front yard in Venice when I noticed a girl pull up and park. She sat there for a few minutes too long and looked quite frazzled. I was half-tempted to go see if she was alright, but sat back and let her be until she got out of her car and approached my front gate. In disarray, she explained how her phone had just died and she was trying to meet up with someone nearby but couldn’t remember the exact address and asked if she could charge her phone inside my place. Now normally I wouldn’t let just anyone into my house without knowing them, but let’s just say she was without a doubt attractive, not to mention had a pretty revealing top on, and I figured what’s the worst that could happen? So I let her in and we both engaged in awkward conversation on my couch while her phone charged. She seemed alright, but I kept getting the vibe she had something more she wanted to say, which is when she eventually let me in on the fact that she was sorta seeing someone. She went on, ‘Yeah, but he’s kinda famous, and it’s not suppose to be known that we’re hanging out because he sorta has a girlfriend.’ I said alright and wasn’t even going to press who it was, but she finally revealed that the “kinda famous person” was lo and behold Robert Pattinson and that she was reluctant to meet up with him at this party she was headed to. When her phone was at a decent enough charge to book it, she abruptly grabbed her things, and awkwardly stood there. I must have been making inappropriate eye contact at one point or another, because she then went ahead and goes, ‘You could touch ‘em if you want, for letting me charge my phone and all... ’ Yep, she was talking about her boobs. However, I got the feeling she was crazy, plus they clearly were fake, so I sent her on her way.”

-- Tony, Venice, 29

This girl quickly realized the true meaning behind Netflix & Chill...

“When I got back into the dating scene, I had just come out of a four-year relationship. I was a noob when it came to apps and LA dating etiquette, but I dove right in. I met a guy on Hinge who seemed totally normal on paper: Ivy League engineering grad, good-looking, charming, we had a friend in common and most importantly there was textual chemistry. We’d been texting for a while when I suggested that we hang out for a casual day date. The exact words I used? ‘Let’s chill and maybe watch something on Netflix.’ Now... I’d never heard of ‘Netflix & Chill,’ but I was quickly about to find out what I’d gotten myself into. I show up to his apartment, thinking we’d probably grab a coffee first and he opens the door half naked in boxer shorts. Awkwardly, I suggested he put some clothes on (he did), and I spotted a roommate walking around so I felt a little less weirded out about things. He started talking a lot about his Mom and how close they were (... like, a little TMI for a first date) and after about 15 minutes of small talk he excused himself for a moment. I was taking in his living room decor while (I assumed) he was getting his jacket to leave, when two seconds later he comes up behind me, wraps his arms around me in a bear hug, and starts *intensely* smelling my hair and kissing my neck. At this point, we’re about 30 minutes into the ‘date’ and I immediately burst out in uncomfortable laughter, pushing him away. He says, ‘I thought this is what you wanted?’ I said, ‘Um, fuck no -- BYE -- and literally ran out the door.’ Later that day, I recounted the incident with my 63-year-old father who comically explained to me -- his 26-year-old daughter -- the exact nature of ‘Netflix & Chill.’ Lesson learned.”

-- Elle, Mar Vista, 27

This girl endured a not-too-romantic Tinder-Bumble love triangle...

“I met this guy on Bumble who I quickly hit it off with and we decided to meet on a Thursday night. The date went well and I even went back to his place. We saw each other a couple times after that, but it wasn't until a few weeks later that I discovered that he had also gone on a first date with a co-worker of mine (she actually sits right next to me at work) only three days after our first date. Now, I know what you’re thinking, what a coincidence, but he probably didn’t realize his mishap and that we both worked together. But oh no, he knew where we both worked and proceeded to schedule two first dates with us, me on Thursday, and she on Sunday. After our revelation, I ended up sending him a picture of the two of us together that said: ‘My friend says hi!’ I only wished I could have seen his reaction.”

-- Natalie, Glendale, 26

This guy let us all in on the secret to dodging a hefty bar tab...

“I met this girl on Happn and we quickly hit it off. I asked her out on a date to grab a few drinks and she obliged, so I took her to one of my local watering holes in Venice, right off the beach. I’m a Scotch guy, plus I wanted something I could just casually sip on, so I chose my go-to $25 a pop Scotch, and when it was her turn she just said, ‘I’ll have what he’s having.’ First thought running through my head is ‘Well shit, this is gonna be an expensive date’ being that one round was $50-plus bucks. However, things of course ended up going surprisingly well, which in turn led to another round, which eventually led to another round (so now we’re looking at an almost $150 tab). It wasn’t until the end of the third round that I see out of the corner of my eye a cockroach creep across the bar. I, while in shock, kept myself composed and quickly put a paper coaster over it, but the bartender must’ve seen my reaction because he immediately darted over and asked if everything was okay. When I explained what had just happened he was naturally horrified and embarrassed being that it was a rather upscale bar and without hesitation goes, ‘Your bill’s on us. Don’t worry about it.”

-- Anthony, Venice, 29

This girl quickly found out what it’s like dating a method actor...

“I was perusing my Instagram feed one day when I came across a photo that my friend Ron had posted, and he was standing with a gorgeous looking fellow. I immediately texted my friend Ron and asked who his friend was. (I'm forward, almost to a fault. Well, totally to a fault.) When Ron said that it was his friend Gabriel, and that he was single he offered to give him my number. I was thrilled.

“Gabriel texted me and we flirted a bit, and then he asked me out on a date. A real date, in LA those are few and far between. We made plans to grab drinks at one of my favorite bar/restaurants in Studio City. 

“We met up, and it was awkward from the beginning. His nonchalant, ‘I could care less if I was on a date’ attitude was bothersome. We walked through a residential area to the bar and talking to him was like pulling teeth. Every question I asked was met with one-word answers and he really didn't seem that interested in me. After one drink I was ready to GTFO of there, he kind of gave me the feeling like he was over the interaction. He wasn't interested, which was okay with me.

“He was walking me back to my car and as we turn on the street I was parked on, he lifts me up off the ground and kisses me. Out of nowhere. Honestly, I think he and I were on separate dates because he seemed to think it was going SO WELL that a Dirty Dancing moment was necessary. I was so confused, but it also wasn't the worst kiss, so I participated. After a few minutes of a high-school-esque make out session, he pulls away and says,

"‘I'm dangerous.’

"‘Um, ok?’ I grabbed my keys and began to walk to my car. He says behind me:

"‘I'm no good for you. You shouldn't be near me.’


"It should be said that this guy was exactly my size. He didn't come across as dangerous, and I probably could have kicked him in the nuts and ran off if he tried anything inappropriate. It was just his demeanor, like he needed me to know he was ‘dangerous’ and he wanted me to like that he was ‘dangerous.’

“I walked to my car, got in, drove away, deleted his number, and sent Ron a text that said: WHAT THE HELL. We never spoke about it again. 

“Turns out, Gabriel was an actor. And this ‘date’ was used for ‘method acting’ for a role. Now I don't know if he actually wanted to go on a date, or if I just popped on his radar at the right time. I also don't know how truly dangerous he is, but if you ask him, he'd probably say ‘Very dangerous.’ Oh, LA, only in you.”

-- Kayla, Valley Village, 28

This girl and her date got hot and sweaty real quick, going on a yoga first date...

“I matched with this guy on Tinder and we hit it off right away between our shared love for the show Friends, The Bungalow in Santa Monica, and yoga, which led to us discovering that we also practice at the same studio -- pretty big coincidence considering there’s a yoga studio on just about every corner in LA. I also had just gotten certified to teach and he was considering doing the same and wanted to pick my brain so he suggested we meet up and take a class together. I thought it’d make for an interesting first date, plus I figured if it didn’t go well at least I was getting a workout in. So we decided on a day and time, and when I arrived he was already in the studio. We spotted one another almost immediately being that it was a pretty small spot and he looked just like his pictures -- good start. The class ended up being not only hot yoga, but also 90 minutes vs. the typical 60, and being that it was yoga and we couldn’t speak when we wrapped up I wasn’t sure how to proceed. Should I go shower, should I just go out sweaty and gross, what if I did that and he went to shower? So I naturally went with taking a super quick shower and went out where he was waiting (un-showered). He asked how I liked the class and we talked about some yoga related things as we perused over to our cars in the underground ramp before he then asked for my number. I said yes, gave it to him and then he said he didn’t have service but would text me when he got out. He then awkwardly said how he’d hug me, but he was all sweaty and gross so he proceeded to stick out his hand and we shook hands like we had just completed a business transaction. I literally mouthed WTF as I walked to my car and was sure I wouldn’t hear from him. But minutes later I got a text saying, ‘Hey this is D**** Let’s do this again.’ I thought weird, but said ‘Definitely’ and left it at that. Never heard a word from him after that until about a week later when he added me on Snapchat. No conversation, no further follow up via phone, or run in at the studio, but now we’re Snapchat friends. So there’s that.”

-- Taylor, Santa Monica, 27

This girl fell for the boy-next-door type, quite literally...

“A year ago my upstairs neighbors threw a holiday party and invited me and my roommates. Four months prior when the three boys had originally moved in, I had done the obvious thing and had taken every piece of garbage to the dumpster in order to thoroughly scope them out. One seemed normal, one reminded me of Tarzan, and one was simply The Other One, but none seemed like prospects for a notch on my bedpost. When party day rolled around, I resigned to going with one of my roommates. I spent most of the night talking to The Normal One since he had helped me carry in my groceries once and we had that to go off of. About halfway through, I found myself standing awkwardly next to The Other One -- who I soon found out was of course an actor/musician type. He asked me what kind of music he should play and we started talking. To my surprise, he wasn't that bad. He then asked me if I wanted to hear a good piece of writing and led me to his bedroom where he proceeded to read me a quote about death. He then told me he was attracted to me, I giggled awkwardly, and after a very weird silence, he suggested we get back to the party. I managed to stay at the party long enough to see him go into his room with another girl -- to probably read her the same quote about death. I don’t know what it was, maybe it was because he was cuter than I remember, or maybe because I just wanted to be able to say I banged one of my neighbors, but my jealously fired. I went back to my apartment, found his number on a note they had written us about getting in touch with them over missing mail weeks ago and texted him, ‘Wanna come downstairs and play?’ Almost immediately he replied with a ‘YES!’ He left the girl that he was talking to and came down to my place. Excited he told me he had noticed me that first day when they were moving in and he was too nervous to talk to me, which is why when he led me into his room earlier all he could do was think to read the first thing he had laying around his room, which unfortunately had been about death. He had assumed I had been creeped out, which is why he suggested we get back to the party. I told him that it was creepy, but I'm also a winner and I didn't want the other girl to get to him first. Long story short, he spent the night, and while I was on a yearlong Tinder binge, swearing off second dates left and right, because the last thing (I thought) I wanted was something serious. However, the next morning he suggested we grab brunch (something I’d also never do as it warranted seriousness), but I obliged and we spent the next string of nights together almost inseparable. We eloped five weeks later, and are now currently expecting our first child together.”

--Lauren, Sherman Oaks, 30

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Taylor Casey is a freelance writer based in Los Angeles who feels slightly better about her dating life after writing this piece. Follow her on Instagram and Twitter @taylordcasey to swap dating stories.