These ‘Whoa, Didn’t See That Coming’ Dating Moments Are Freaking Hilarious

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In the immortal words of Bill Shakespeare, the course of true love never did run smooth. And some romantic speed bumps can completely blindside you! 

So a Reddit thread recently posed the question: what was the biggest relationship thing that redditors never saw coming?

And the answers will definitely blow your mind. From cosmic coincidences to grand epiphanies and even a surprise stalker or two, these people have pretty much seen it all. Keep reading and you’ll find some truly epic relationship plot-twists!

Of all the tiny things to totally explode over…why this?

I was having an amazing time talking to a guy I’d just met on Tinder. He was sweet, funny, and lived about 5 minutes from me. He asked me out on a date, and I was ecstatic.  The day comes, and he offers to come pick me up. I politely decline, and I decided to be honest with him and say I wasn’t totally comfortable being picked up by someone I hadn’t met quite yet, and that I’d rather meet him there myself. He seemed nice enough to take it well, I even told him it was based on a prior bad experience. He freaked. I have never been called more names/things in my entire life. Distrusting, rude, nasty, ungrateful, the list went on. I didn’t even fight him.  Dude literally tried to evaluate my entire psyche, ranting and “explaining” what was wrong with me for not allowing him to pick me up, then blocked me. I’ve never seen someone take such a hard left turn into crazy town in my life. Janzey

Woah, too soon!

A girl mentioning moving in together after the first date. –B0NERSTORM

This is a weird time to ghost someone.

One of my ex’s practically disappeared. I couldn’t figure out where she went or what happened to her until her dad called me and told me she didn’t want to see me anymore.  We were both 21 and had been together a few years. –MrBootmen241

This person went to a party with a psychopath.

Went to a party with a guy. When I got there, he basically ignored me and flirted with some other chick most of the night. Later at night, they followed me to my car when I was getting something out of my trunk for the party.  Guy shoves and locks me in my own goddam car trunk once I opened it. Can’t find the latch, super drunk and terrified. He’s laughing hysterically outside the car, trying to use it as flirting fodder with the now horrified other girl.  She’s not a psychopath like him and helped me call someone with spare keys… I got out eventually, super embarrassing though.CrankyCookies


I dated a 22-year-old who took her teeth out to eat an ice cream. Totally didn’t see that coming and tried to make her feel comfortable. I didn’t keep seeing her for other reasons, but yes, I experienced the missing teeth that night.saburling

This is plain upsetting.

I dated someone for two years, then we moved in together. About a year and a half into living together, I’ve met all of his friends, his brother, and sister-in-law, we traveled together, we had a mutual friend group, we went on IKEA runs and all of that cute shit.  At that point, we weren’t doing any serious planning, but the discussions were taking a turn more for ‘when’ not ‘if’ on things like marriage, kids, and buying a house. Basically, we weren’t saying let’s get married but it wasn’t far off the table still. Then one day it just went radio silent. For context, we had a guest room and sometimes when we got in arguments or one of us came home really late, we would sleep in the guest room (either to give each other some space or to not wake up the other person).  He started coming home and going straight to the guest room and closing the door. We used to talk pretty consistently throughout the day by text or dumb Snapchats or FB chats and they all stopped. He had just started a new job so I tried to check in and being there for him.  I’d send the occasional supportive text or ask him how things were when he got home or if everything was okay. I’d usually get a ‘fine’ text hours later, if at all, or a ‘nothing’s wrong’ and a door shut in my face. I tried making him his favorites for dinner and he’d order from GrubHub instead.  I’d get texts from our friend group saying they’re sorry I couldn’t make it out for drinks or whatever, even though I was never told about it. There were times where I’d get frustrated and we’d have arguments where he’d say again that nothing’s wrong and nothing’s changed. After about four months of that on cycle, I told him basically I don’t know what else to do. Everything I’m trying to do to understand what’s going on or be supportive seems to be making it worse. I’m here if you want to talk and when you’re ready. For the remaining three months of our lease, he was bringing over his new dates and banging them in the guest room or making out with them in the living room. I never got an explanation of what happened. A few mutual friends during that last three months said he told them that I wasn’t talking to him anymore, which was true, but because by that point I had given up. And frankly, had no interest in talking to him anymore.ridersderohan This Redditor’s guy didn’t even deserve the support they were offering towards the end there. Sheesh.

This feels like the start to a horror movie.

In college, my roommate and I moved a mutual friend into our place because his roommate had some mental health issues and was stalking him, and doing some really messed up stuff (like threatening to hurt himself unless a friend hung out with him).  I never met nor saw the roommate. About a month later, I get asked out by this random guy on a dating website and it seemed fine, so we go out for pizza. As the date unfurls, it slowly becomes more and more awkward as the guy asks about my living situation, friends…roommates.  The whole thing just feels awkward. We say our goodbyes and I go home, to tell my roommate about it…and then the lightbulb goes off. It was the stalker guy, trying to get info about him. There’s actually a fair bit more to this story, but that’s the basic scenario.apathyontheeast

The plot thickens:

To clarify, all of the characters in this story are guys (I’m gay, the stalker is also gay, roommate/stalkee is straight). I’ll parse them in as they happened: Probably part of the reason the stalker got so infatuated with the stalkee is that he was the first person the stalker came out of the closet to and he reacted well (as the stalker came from a very Catholic family).  This was all about 15 years ago and attitudes towards LGBT people still weren’t great, particularly in the red state in which we all lived. I have no idea how the guy found me, but sexuality probably plays a role. I’m a gay guy in a fairly small town and the stalker knew that he had gay friends, so going through the online dating profiles/Facebook/Myspace at the time was probably not too hard for him. The stalker ended up harassing my friend a few more times over the years, showing up at his work to drop off important personal effects he had left behind during the move (e.g., a clothes hanger). –apathyontheeast

These people had a sizable mutual misunderstanding.

Met a guy while walking to work. It was dark out but not in a creepy way. We run into each other a few times and I ask him out. We go for dinner and he tells me about his work history, says he did something in construction for 15 years. I am 20 when this happened.  Turned out we were both really bad at guessing age and he was in his forties and thought I was in my late 20s. Luckily, he could tell I was weirded out by it and didn’t contact me after. –mountainsprouts

If this happens to you…run away.

Went to a girl’s house to meet her parents and they sat a teddy bear at the table, gave it food and drink. She was the youngest in the house at 23 and the bear was such a recognized member of the family it had a Facebook page. The weirdest part is when they would do voices for the bear and make me speak with it.BoyGirlSmoke

But also, this little speed bump:

Family also hated me as they were super religious and I was born out of wedlock.BoyGirlSmoke

Thanks, but no thanks.

I took a girl out on our first date. I guess she was trying to impress me because she rattled off the list of guys whose virginity she’s taken. Spoken in a way suggestive that, if I played my cards right, something good may happen to me. I was not interested nor impressed.Braydeennnn

COPS marathon and chill.

Might seem minor or silly but the first time my girlfriend didn’t want to go bar hopping on a Friday she asked me if I was cool just coming over, drinking Miller Lite, and watching a Cops marathon. She specifically said it was a tased and confused special. I never thought I’d hear a girl say that. We’ve been married for two years now.CarlOnMyButt

They should’ve seen the engagement coming, really.

On my first date with my current fiancé, he told me that he has two older sisters that are both married to guys named Cody. Guess what my name is?GarshCT (OP’s name is Cody too, BTW.)

You never know when you’ll meet someone who denies the existence of dinosaurs.

Met a woman for dinner after chatting online for a few weeks. She’s super cute, the conversation is flowing well, we’re really hitting it off. I’m talking to her about my work, how I get to meet all kinds of interesting people including a man who pulled me into a discussion about Bigfoot for 45 minutes that I couldn’t tap out of. Her reply? “I don’t believe in Bigfoot, or aliens…or dinosaurs.”  I had heard of people that believe that the Earth is only 6000 years old and the Devil put the dinosaur bones here, but that was the first time I had met one in the wild.MrPaulyG

It’s like two ships passing in the night…but then they actually meet a year later!

We had a yellow-umbrella moment. On our first solo date (first was a blind double date), we were talking about how we knew some of the same people. I told him I had gone to a party that year where I was really drunk and a huge fight broke out between like 12 people at a house party on the front lawn.  I saw some glasses on the ground so I held onto them so no one would step on them. A guy then came up to me asking if I had seen some glasses his friend dropped.  Turns out he had the same story about trying to break up a fight at a party and finding that his friend’s glasses were picked up by some girl. We also had talked to the same people at the party, but at different times and never bumped into each other. That guy is my husband now. –ForElise47

‘Red Flag’ doesn’t do this justice.

Met a girl online. We chatted a lot and she seemed like perfect girlfriend material. We had arranged to meet up a few times, but due to her/my work, we always had to cancel.  After a few weeks of chatting on a daily basis, she suddenly, out of nowhere, tells me how she fantasizes about locking me in her basement.  Not kinky lock me in the basement…rather tie me to a chair and keep me there as her prisoner indefinitely, so she can do to me what she wants when she wants.  She would also be in charge of feeding me and cleaning up after me. She spared no details about her plan. I honestly don’t think she was joking and I cut contact with her shortly after that conversation.hmfiddlesworth

Unexpectedly finding out your boyfriend is a keeper:

First time going to my now-fiancé’s apartment. He had gotten drunk after a bad day at work. Not just drunk, but absolutely hammered. I drove him home, helped him up the three goddamn flights of stairs to his apartment, and opened the door. He apologized for the mess. It was clean! There were some cups and video game controllers on the coffee table and a pair of pants on the couch. That was it. That was the mess. Other than that, the place was immaculate. It was well-decorated, organized, the carpet had been vacuumed recently, and it was full of really nice stuff! He asked if I wanted to go to bed with him. (We hadn’t had sex yet.) I told him he’s too drunk to make good decisions. He said, “Oh…you’re a good adult. I’m super drunk. Thanks for looking out for me.” He wandered into the bedroom. I waited a minute for him to come out and say goodbye, but he didn’t. I went into the bedroom and found him lying in bed, flat on his back, snoring. So, like a good adult, I set a glass of water and a few Advil on his nightstand, left a note saying I’d pick him up and drive him to his car the next morning, and locked the door.insertcaffeine

Finding creative ways to tell someone about yourself:

Was casually dating a girl for 3 months or so, she suggests we watch some porn together – ok cool. So she puts a DVD on (this is 2008) and the second scene was HER. Totally unexpected. Was cool but I found it sort of an odd way to tell someone that.villan22

Let go of your preconceived notions on who is ‘right’ for you.

I coached a young girls soccer team (6-7 yo) about 12 years ago. My assistant coach’s wife was always super nice but never really caught my eye because she was much taller than me (5’11-5’8), and married. I’ve never been secure enough to be attracted to or date a taller woman. Fast forward to a few years ago. We’re both divorced after our spouses cheated. We run into each other. We go on a friendly lunch date. I’m blown away that I never noticed how beautiful and wonderful she is. We kiss in the parking lot with people laughing at us!  We now live together…and she is the most amazing woman I’ve ever met. Complete package. Sweet, kind, no games, fun, funny, beautiful, great job, my kids love her, etc.  Never would have seen us together but glad I’m now confident enough to date a taller woman. So glad I went on that “friend” date! mowtown1

Romantic epiphanies are always nice.

I had never chased love. I had a lot of bad experiences and was tired of the outcome every time. Met a girl through a mutual friend, she was really extroverted at first, I’m more of an introvert and prefer 1 on 1 time with someone rather than groups. It was going pretty good for the first couple of weeks. I definitely had feelings for her, strong ones too. I always thought I was gonna live to be a hermit and alone by myself all my life. That all changed when we went to Walmart at 11 pm just because she was craving frozen pizza.  I never thought I’d be able to process having such big feelings for someone, but when I saw her in my sweatshirt and pajama pants walking out of Walmart on a drizzly night holding a frozen pizza and looking like the happiest thing ever I just knew that was the one I want to spend my whole life with.chazeltine

How will I know?

Started dating a girl and she seemed nice, but I wasn’t sure she was into me. A few months in and she starts talking about future plans and marriage. I was happy as I was on board with that, but it just seemed like some switch had been flipped. I had passed whatever tests needed to be done. I had made it. Skip to now, we’re engaged and all is good. It was a strange transition though, from “Hey, I like this girl but I wonder how she feels?” to “Woah! She’s totally on board!” in a day or so. –PapaOoMaoMao

The Redditor also explained the shift:

This was a while ago though. I asked her about it later on and she explained it all. Mostly shyness. We’re both very invested now.  Making a life together is a big step but we’re both leaving very solitary lifestyles so it’s a two-sided investment.PapaOoMaoMao Aww, how sweet! All’s well that ends well.

To date or not to date?

Asked a girl on a date. She declined as she was busy but from the tone of her voice I guessed/hoped that maybe she would be interested. So a few weeks later I ask again. She enthusiastically agrees. Awesome! Date, time, location all set. About five minutes into the date she casually mentions the existence of her boyfriend. I had no idea. This was not a date, apparently. I hustled through that date, I mean, not-date. drsameagle

You know what they say about first impressions.

I was dating what I assumed was a white girl for a few weeks. Woke up one morning to her speaking very fluent Spanish on the phone to someone. Turns out it was her mom, she was 100% Mexican. Her name was Paola, she pronounced it “Paula” when we were introduced. Didn’t really change anything about the relationship, but definitely unexpected._quickman

Another Redditor could relate to the surprise:

I had a similar experience with my now-husband. When I met him, he went by a really American name (e.g. Bill) and seemed totally American. We were on our third or fourth date, in the car driving somewhere, when his phone rang. He answered it and started speaking in fluent Russian. Turned out he immigrated from the Soviet Union right before it dissolved and grew up speaking Russian at home with his parents. I was like, “Oh!” Unexpected, but cool.LilyKnightMcClellan

This story is a ride from start to finish.

Opened Grindr. Saw a guy who looked pretty cute at first like 84 feet away. Realized it had to be one of my neighbors.  Thought to avoid it. I had seen enough small town issues and didn’t know if I liked the idea of seeing someone who lived that close to me on the app.  He started messaging me though. “Wow. You’re really close.” We started talking. Found out he was actually my neighbor’s brother. He wanted to meet. I said sure, let’s go for a walk. We met down the street and started on the walk.  The first thing he told me was that he was so high on crack and that his brother was running a meth lab. I had to just be polite and try to get through the walk. I wanted to end it from the beginning though. Later his brother got raided and arrested right next door because another neighbor called the police after she heard a fight.ZeusDX1118

Oh, the colorful individuals you’ll meet on Tinder.

Went on a tinder date a few years ago, he seemed really nice, we went on a few dates but each time he always said something odd. First date: ‘Its cool that you go to the bathroom and leave your bag on the table with a complete stranger’ Did not leave my bag unattended again.  Second date: ‘I didn’t have a date for a family wedding, so I went with my cousin (nothing wrong with that I thought), we kissed practically all night, people looked at us a lot’. Erm... –cloy23 (Spoiler alert: there wasn’t a third date. Thankfully.)

Never say never.

Grew up in a military town in the south. I always told anyone who listened “I’ll never ever date a soldier.” And “I hate country boys, I’ll never date one.”  So what does life do? Throws me a young man from South Georgia that was stationed in my town when I was in my first semester of college.  I didn’t see it coming because he was the exact opposite of what I ever envisioned myself dating, but I’ve been with him for over 3 years now, and he’s the silliest and best person in my life. –happy_citrus

When you meet your life partner for a joke:

I’ve posted about it before, but I approached my now wife entirely as a joke. My buddy was down, and I thought it’d cheer him up to get a laugh.  I don’t have much luck with women, I am quiet and nerdy and not much to look at. So I picked out a pretty blonde girl at the college cafeteria and decided to go hit on her. Usually I would never, but I was a little buzzed from the night before and thought it’d be funny. I figured she would tell me to go away and it would be hilarious. Just a brutal public shut down that I, to be totally fair, deserved entirely. We talked for a few minutes. She was very nice. I stopped short of asking her on a date, so I guess it was just wildly unprovoked small talk. Anyway. Yeah. We had a class that semester, and with the ice broken, I just talked to her like a normal person. We have two kids now. Did not see that coming.soomuchcoffee Share these entertaining, romantic twists and turns with your friends!