The Best, Worst, & Most Awkward Dating Stories From The 2010s, According To 50 People
When the 2010s began, my most serious relationship to date had been with a boy I'd met at age 12. We had starred in a summer camp production of High School Musical together as Troy and Gabriella. We held hands a couple of times and almost kissed once, but our relationship went on to dissolve through a string of unanswered texts. Ultimately, he was from Connecticut, and I, from New York — we were too young to be in a long-distance relationship, and our breakup didn't sting too much. Besides, something told me my best dating stories were yet to come.
Boy, was I right about that: The last decade brought on unimaginable heartbreak, puppy love, and uncomfortable sexual experiences that I still can't wrap my head around without cringing. I had penetrative sex for the first time, then went months without sleeping with anybody at all. I gave up on looking for love, then found it unexpectedly in the last place I'd thought to look. I flirted with friends, went on disastrous dates, shared intimate moments with strangers, and learned a whole lot more about myself in the process.
So, what did I discover about love, sex, and dating in the 2010s? At first thought, not much. But when I dig a little deeper, I think my biggest takeaway is to allow yourself to be surprised by the people you date. Going into a decade of dating with too many expectations can place unnecessary pressure on both you and the people you meet. Love is a little bit like art: You never know when inspiration will strike. Curious to find out more, I spoke to 50 people about their best, worst, and most awkward dating stories from the last decade. What they had to say will make you laugh, cry, and perhaps most importantly, reminisce.
1. Metro Meet-Cute
I kept seeing a very cute girl on the metro during my morning commute and finally got the guts to say 'hi' to her. We ended up dating for a year and a half!
2. Never Been Kissed
The first girl I ever kissed forgot about said kiss. It was obviously a big deal to me. She asked me out and while we were talking on the date she asked me if I'd ever kissed a girl and I had to say, 'Yes, you. Last week.'
3. Across The Crowd
I was seeing this girl for a few weeks who bought me tickets to go see Maggie Rogers with her (without me mentioning that I had wanted to go!). I had a wonderful time at the concert. But only two weeks later, she texted me that things got too serious and she had to end things. Fast forward five weeks: We're both at the same Lucy Dacus concert, and she saw me at the show. So, she texted me at 1:00 a.m. saying that she couldn't stop thinking about me during one of her songs. Now we're hooking up again.
4. Take A Chance On Me
Last Valentine's Day, my boyfriend knew how much I loved the movie Mamma Mia 2, so he planned an entire night around it: He booked us a private karaoke room to sing songs exclusively from the soundtrack, gave me gifts themed around the movie, and capped the night off with a Mediterranean feast to fit with the movie's setting. It wasn't the standard Valentine's Day by any means, but it was so touching to me because it showed how completely he knew me.
5. The Name Game
The guy I had a crush on started dating another girl, and her name was also Hailey. I found out he was dating her from his little sister, who texted me saying how glad she was that he finally made his move on me! We did end up going to prom together our junior year, but nothing more happened. Still not sure why I said yes. Oh, high school.
6. Teardrops On His Guitar
I had been dating a guy (think: tattooed dude with that annoying LA confidence, but literally nothing to back it up) for about three months when I discovered he'd cheated on me. I took him back, and about two months later, he proceeded to move into my apartment. Fast forward: We'd been dating for about a year, and I went on a week-long business trip to New York. Everything seemed fine when I called him from JFK before boarding my flight back, but when I get back to my apartment in LA, I discovered he had fully moved out without telling me, leaving only the guitar that he didn't know how to play. He proceeded to leave me a single voicemail that night, then texted me the next day apologizing for not being '100% available right now.' What a piece of sh*t.
7. Spill The Tea
I met this guy and started hooking up with him, and my best friend also started dating his best friend. It was nothing special because he was kind of distant. It ended mutually, no big deal, and we didn't see each other again. A year later, I was working at a music festival and I ran into him with his new girlfriend. He acted very strange and didn't say anything. He then texted me an hour or two later asking to catch up over a cup of tea. He also told me that his girlfriend thinks I'm very pretty. Guys are weird.
8. Giving Up The Ghost
I turned 25 five days ago, and the guy I've been casually dating for four months didn't show up to my party and has been ghosting me since.
9. Touch & Go
I started, then very much stopped, then started once again dating the love of my life. Spoiler alert: We got engaged. So, it all ends up OK.
10. Exes & Oh-Nos
I went on a date to get drinks with a girl I liked and we bumped into the girl's ex. So, we left and went to another bar, then bumped into another one of her exes. Then the first ex from bar one somehow ended up at bar two, and I knew it was time to go home.
11. Bleeding Love
I went on a first date on Valentine's Day. It should have been romantic, but my date got a nosebleed while we were kissing. He bled into my mouth! It was so gross.
12. An Unexpected Run-In
One Fourth of July, I went to a vineyard in Virginia with some girlfriends. The sommelier was super flirty and asked for my number, but I had just gotten out of a three-year relationship, so I gave him a fake number. That night, we were out at a bar in Washington, D.C., and he ended up coming to the bar. I was super freaked out! How had he found me? For months after, I continued to run into him at bars.
13. A Scoop Of I-Scream
I was on a first date with a guy and it was going pretty awkwardly. We had no chemistry whatsoever and the conversation just didn't flow. I figured the date would end after dinner, but he suggested we get gelato and eat it in a nearby park. We sat on a bench and he asked if he could try a bite of my gelato. I said sure. He used his own (used) spoon to scoop out a bite, then said, 'Now that my germs have been in your food, they can be in your mouth, too,' and planted the sloppiest, most intense kiss on me. Years have passed since this date and that line still haunts me.
14. Send Noodles
On my first date with my girlfriend, we went to a tiny Italian place and shared bowl of spaghetti after bowl of spaghetti until the restaurant closed and we were the only two people in the room.
15. Slumber Party
I really liked this lad named George in high school. One weekend, his parents went out of town, so I made banana pudding and picked him up at his house and drove him to the beach to eat the banana pudding. Then we went back to his house where we watched a Sergei Eisenstein movie and ordered a pizza and drank a bottle of wine. I fell asleep there, and it was my first romantic sleepover.
16. Wherefore Art Thou Romeo?
My boyfriend and I always compare our relationship to Romeo & Juliet's (without the dying at the end), so one year, for Valentine's Day, he took me to see the play. It was super romantic.
17. Friday The 13th
I got ghosted by my boyfriend of three years on Friday the 13th. That's it. That's the Tweet.
18. Group Date
My boyfriend brought his best friend on our first date, then proceeded to ignore me the whole time.
19. Pure Comedy
I had been dating a guy for about nine months. He was a comedian, and I went to see him in a show, only to be seated next to another girl that he had been apparently dating, too! They're still together and have adopted a cat.
This one time, I went out with a friend and told her that I didn't want to go home with anyone, but if I changed my mind, I'd use the code word 'Jigglypuff.' Anyway, I ended up meeting this hot guy and realized that I'd have to work the word 'Jigglypuff' into the conversation, so I ended up telling him and his friends, in front of her, that Jigglypuff was my favorite Pokémon. She was trying so hard not to laugh. Later that night, I took him home and we accidentally bumped heads as we went into kiss, and he nose started bleeding. I regretted saying Jigglypuff.
21. Looking Like A Snack
Once I was dating a guy I’d met in my pre-med program and brought him home one weekend around Purim. We went to go make hamentaschen with my nana and were snacking on fruit — at which point it was revealed that this guy, 18 years old, pre-med, from California, had never eaten a raspberry before. The relationship lasted maybe a month or two longer.
23. After Dark In The Park
My second ever date with my now-girlfriend, we just danced around a park together, then hooked up for the first time in the park. It was super romantic.
24. Very Formal
This girl who was closeted asked me to her sorority formal and I was so, so excited. But when we got to the after-party, I realized that it was at a bar that was 21+, and I was 20. She went without me. It was the most awkward experiences of my life. Can you imagine being left outside a dive bar in full formal wear?
25. I Think You Missed
When I was 13 (exactly 10 years ago), I mustered up the courage to kiss the new girl at school. We were at my house taking selfies on photo booth, and we were kissing each other on the cheek. By accident, we both turned heads, and she ended up kissing my nose. Then I said the smoothest line in history — 'I think you missed'— and I kissed her on the lips. Thirteen-year-old me was smooth AF.
26. Tongue Tied
When I was 16, I wingman-ed my friend to the house party of a guy she liked. When we arrived, it turned out to be just us, her crush, and another guy. Within 15 minutes, those two went off into a room to hook up. The other guy, a ginger with braces, turned to me and raised his eyebrows. We started making out, but five minutes later, he pulled away and told me I used too much tongue. I'm still insecure about my French kissing.
27. A Loyal Follower
I was studying abroad and went on the most perfect date with this beautiful British man. It was definitely too good to be true because on hour four of this date, he decided to tell me that he found my YouTube channel and watched all of my videos! From then on out, he would finish my stories for me because he had watched them already in all my vlogs. It was so uncomfortable. To make it worse, after I changed the subject, he asked me about something I did in high school that he found in the depths of my Instagram.
28. On Holiday
Last December, I was leaving work when I heard a British voice beside me ask, 'Are you from New York?' I turned around to see this gorgeous tall guy in a peacoat with perfect white teeth, who turned out to be (fittingly) a dentist from Wales visiting NYC for the week. We started talking on the street (I normally do not entertain advances from strangers while I’m on my commute) and ended up going on a date the next day. We hung out and hooked up a few more times over the course of his visit, he flew back to Wales, and we haven’t spoken since. It was the perfect little holiday fling and such a fun memory
29. Urine For It
The first time I was eaten out by a guy, I told him to stop because I was really afraid I was going to pee. He told me that what I was feeling was very normal and basically the same thing as orgasming. Long story short: He was wrong and he paid for it.
I told my boyfriend of eight months that I loved him and he said absolutely nothing. He pretty much pretended like he didn’t hear me and that it never even happened. A couple days later, I confronted him about it and ended things with him after he said 'IDK' to every single question I asked him about our relationship and his feelings for me. God bless America!
31. When The Beat Drops
When I was a freshman in college, I hooked up with a guy who exclusively liked to have sex while listening to pretty aggressive EDM music. I found it super distracting and asked him to turn it off, but he refused — he liked to orgasm at the exact moment the beat dropped. I do not miss being 18.
32. The Perfect Present
In college, I had a giant crush on one of my friends and all of our friends knew it. We did a Secret Santa swap that year, and the person who had me got me the craziest gift: A picture of my guy friend, naked, with a ribbon covering his junk. Thinking about him being asked to pose for that photo was too embarrassing. I nearly died.
33. Show Me Your Teeth
This was the best and worst. Five years ago, I went a first date. We were on a bicycle ride through the Oakland Hills and on a descent, I crashed and lost my front teeth and a lot of skin. I looked like I had no teeth! I had him immediately take me to the dentist to get my teeth fixed. One of my teeth was actually found in my hair later. But he came over every day after that to change my bandages and bring me food, and we've been together ever since.
34. Euro Trip
I dated a guy for three-ish months. After three weeks or so, we were spending four nights per week together, sleeping at each other’s apartments, meeting each other’s friends, and doing lots of activities (going to Broadway shows, dinners, movies, and brunches). I was super close to wanting to define the relationship when he started acting distant. The next week, he went on a Euro trip and I never heard from him again. He wouldn't answer any texts or calls. I think this perfectly sums up the ghosting phenomena of the past decade. It's just a classic and prime example of how ghosting can go (i.e,. not just after a few good dates, but a few good months, too).
35. Booty Had Me Like
In 2017, I had a dating experience so bad that I didn’t date again for a whole year. I went on two dates with this guy who I had matched with on Minder. He was too short for me, but at first seemed decent, respectful, and able to have deep conversations. He was a very religious Muslim, and well-known in the Muslim community as a devout Muslim who was super into social justice. We went on second date and he was into the physical stuff, like kissing my neck and hugging me, but I wasn’t interested in him like that. I didn’t think anything of it and we mutually kind of decided we weren’t feeling it after that. Two months later, he matches with my friend on a different dating app, Muzmatch, and starts off by talking to her about eating a** and how he has a great butt. He tells her he wants to meet up with her and have sex in a park, sends her videos of himself naked on a bed, and much more. I find this out over brunch with my friend, so I text him to let him know that he should be careful because I know his family is very strictly Muslim. He apologizes to me, but then asks my friend what my reaction was when I saw pictures and videos, and he requested a threesome.
36. Give It To Me Straight
This one time, I got a drunk at a party with my mom's friends and started hitting on the bartender (the only person close in age to me). We ended up making out in the bathroom of the house and totally embarrassing my mom.
37. Why Not Me
I was seeing this guy who I really liked, but he had just gotten out of a long-term relationship, which I guess I knew was dangerous, but I didn't care. Looking back, I think I was in love with him. But he told me he wasn't in a place to date someone seriously and broke it off. But it stung 10 times more when he started a seriously relationship with the girl he started dating after me.
38. Abroad Changed Me
When I was studying abroad and living with a host family, I met a cute guy who I decided to take home with me. I guess I wasn't expecting my host mom's son to be sitting in the living room in his underwear when we got back to her place. Not only was it awkward, but we were totally busted.
39. New Phone, Who Dis?
My boyfriend of just over two years ghosted me in order to end our relationship. Literally got a new phone, new number, and moved.
40. Valentine's Diss
A guy I was dating once dumped me on Valentine's Day by informing me that he was in love with his best friend. And this was after I made my sister sit through two hours of his improv troupe's performance.
41. What Are The Odds
I met a hot, blond surfer dude at a club one night. I told him my name and he had this look in his eye, but I ignored it. We ended up dancing and making out, but I didn't get his name or number. The next day, I showed up to work and almost threw up: He was my new coworker.
42. Unfriend & Forget
I was dumped once in high school on Facebook. I actually found out my relationship with my girlfriend was over because she ended our relationship status. It was so brutal because everyone saw the update, too.
43. Message Received
I was in class once, back in college, and sort of secretly swiping on Tinder. I came across a guy who sat in my class a few rows in front me that I thought was kind of cute, so I swiped right. Then I proceeded to watch him swipe left on me. I wanted to melt into the floor.
44. A Beautiful Disaster
I went on a first date with a guy I kind of liked, but was really nervous because he was different from the people I was normally into. Anyway, I was doing most of the talking and getting a little too into the story I was telling him and accidentally smacked him in the face, which made him swat his food all over the floor. It was a mess. There was no second date.
45. A Family Affair
My boyfriend of two years came back from holiday vacation to spend New Year's with me, and my family, and our friends in our Brooklyn apartment. He actually ended up breaking up with me on Dec. 30, in our bedroom, while my family and friends were in the next room.
46. Pagoda Prince
I one time met a guy through Bumble when I was living in South Korea. He was tall, handsome, and I was extremely nervous. We went on our first date to an ancient village an hour from the city we lived in. We spent the day exploring the village and rice patties. At the end of the day we sat by a nearby lake that had a pagoda extending over the water. As the sun went down, the pagoda lit up in a yellow glow. My date pulled me closer to him and brushed the hair out of my face. We had our first kiss and it was magical. We dated for a year after that.
47. A Modelizer
I once dated a guy who told me that he 'normally dates models, but I would do.' Enough said.
48. More Than Friends
In 2017, I fell in love with my best friend. She didn't know that when it happened. As far as I knew then, she identified as straight, so I sadly swallowed my immense feelings for her. Naturally, I still pined for her in silence while we remained friends for about a year. We spent the summer of 2017 doing nothing except lying in her bed watching movies back-to-back. Me spending one night at her apartment turned into me spending five straight nights a week sleeping at opposite ends of her bed, turned into us inching closer and closer every night until our heads were practically centimeters away from each other. One night, she closed that tiny gap when I felt her hand on top of mine. I started sweating, silently screaming, trembling, and grinning all at once. After minutes of our hands touching, then not touching, then touching again, she laced her fingers with mine. Seconds later, we were kissing. A lot. She tells me now she could literally feel how badly my body was shaking. I remind her every time it was because I was so scared of messing it up. That was my first kiss. It was the only one I wanted. Thankfully, we've had many more kisses since then.
49. Is There A Plan C?
I once was having what I thought was sneaky sex with my high school boyfriend, but the condom broke. I had to get to school, but was freaking out, so I sent him out to get Plan B. I didn't realize that he'd be dumb enough to drop it off at my front door, so that my mother would inevitably find it. Oh my god, that was a tough conversation.
50. I Can See It In Your Eyes
Last week, I was cuddling with my boyfriend in bed, talking about nothing. All of a sudden, he interrupts me and says, 'I'll know if you ever fall out of love with me.' I was super confused, but then he added, 'Because every time you look at me, I can see it in your eyes. I can see the love.' It made me cry.
*Names have been changed.