People Share Their Weirdest "Didn't See That Coming" Dating Experiences

Dating can be awkward, especially for the first few dates. Sometimes things can get downright weird though.

Reddit user u/Hammer-905 asked:

"What's the biggest, "Whoa, didn't see that coming" dating moment that you've had?"

Some responses have been edited for content, clarity, or profanity.


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 absoultely 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.



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.



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.



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 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.

Edit: So, I had a couple of requests for additional details. To clarify, all of the characters in this story are guys (I'm gay, stalker is also, roommate/stalkee are straight). I'll parse them in as they happened:

-Probably part of the reason stalker got so infatuated with stalkee is that he was the first person stalker came out of the closet to and he reacted well (as 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.

-The night we moved him in to our house (under cover of darkness while stalker was away), the stalker had called him and told us he was attempting to commit suicide as a result...very slowly, by drinking salt water until he died of dehydration. Prior to that, stalker had spent a few hours driving around town trying to find stalkee's car. We were able to get some professional help for him that night.

-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 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.

-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).

-Stalker showed up in my life a few times since then, too. A couple of years later, I was working for the college and he was running for a minor local political office. His political statement/declaration had him listed as a Ph.d. student in the department in which I worked (a fairly well-known program nationally).

Except, not only was he not a Ph.d. student with us, he (a) never completed his bachelor's degree and (b) was not enrolled as a student for several years. So you can imagine my surprise when one of our staff was like, "Who the hell is Stalker and why does he say he's in our program?" I do think this was just a coincidence, though.



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 was in my late 20s. Luckily he could tell I was weirded out by it and didn't contact me after.


He sounds like a good guy. An age gap like that is just too large (in my opinion), and it is good of him that he respects you enough to leave you alone. Hopefully you can still greet him when you come across him during your walks, as the event is not something to be ashamed of for either parties.



Went to a girl's house to meet her parents and they sit 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.

This will probably be buried but the weirdest part is when they would do voices for the bear and make me speak with it.

Edit: Family also hated me as they were super religious and i was born out of wedlock.



Was casually dating a girl for 3 months or so, she suggests we watch some adult movies 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.

She ended up beating me with a clothing rack pole... Man, Brooklyn was a fun place.



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.


Similar thing happened to me too. a girl I just met started telling me about taking virginity from a guy and laughed about how can someone be a virgin at that age (22). I was 23 at the time and yeah, still a virgin due to messed up past that made and still makes me feel unsafe in sexual situations. Then she told me that her last date left when she left to the bathroom and she wanted to make sure that I will still be here when she comes back from the toilet. I told her that I won't, she took it as a joke. It wasn't a joke.



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.


Before Netflix and Chill, it was COPS marathon and Chill.



On my first date with my current fiance, he told me that he has two older sisters that are both married to guys named Cody. guess what my name is?






Damn I'm good


It's Cody. So three siblings (2 girls and 1 boy) are all going to be married to men named Cody.



So many great ones! I'll do this one since it has a few of those moments in them. I went out with this woman. She's really cool. Great first date, a lot in common, great connection. I reach out for a second date. I hear nothing from her.

Three months go by, I get a text from her out of the blue. She had to have a sudden surgery, so she didn't reach back because of that. We go out, we're still great. Third date, I'm stoked. I figure I'll impress her with one of these Academy films that's getting a lot of praise. Something called The Revenant. Whoops. Figured out what that was in the theater. Did not expect it to be so violent and graphic. And she was super squeamish about watching that stuff.

So we recover at a restaurant and we talk a little. At one point, we're making small talk and talking about our flaws. I say sometimes I feel like I can be a little selfish. I watched her starry eyes go cold and dead to me as I shattered all of her illusions of me. Her responses get quick and she gets quiet. I know exactly what's up. She lost interest instantly.

She gives me a ride back to my car and she just starts trying to figure out what's wrong with her for dating people like me. "Is it because you're an actor?" Then she sinks her head into her hands and says loudly for the quiet person she was, "why can't I date anyone normal!" Well, didn't see that coming. It was hilarious, but I didn't feel like it would be best to laugh there. So I politely ended the date and suggested that maybe we weren't as compatible as we thought. She reached out the next day to apologize and see if I wanted to give it another try. I replied, "Yeah, sure." I never heard back from her, as I now see that the way I phrased that has two interpretations.



Coworker had a huge crush on me. Got my MSN messenger account (this was years ago) from another coworker. He started talking to me back and forth for maybe 2 weeks, and then asked me out on a date. That workplace actually encouraged in-office dating, it was in China so whatever. We went on four dates, each of them great, and then he confessed...he already had a girlfriend.


You know the saying: it's easier to get a job when you already have a job.



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 "Whoa! She's totally on board!" In a day or so.


Be careful friend. i just got out of a situation where it was "I love you see you tomorrow" to "We cant be together anymore" in a day or so.


I get it. 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.



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 didnt want ro see me anymore. We were both 21, and had been together a few years.



My friend had one of these. Girl he had been dating a few weeks just flat out disappeared for a week. No calls nothing. Then she shows up and wants to keep dating. She claims she was in the hospital for a week for emergency surgery. Mmm ok.

Well my friend was getting handsy with her and they were taking their clothes off when he noticed she had no fresh surgical scars or anything like that and she claimed they had done a laparoscopic procedure on her abdomen. He calls her on it and she finally comes clean.

Turned out her and some idiot friends had decided to rob a convenience store with a fake gun. They got caught of course and she was now looking at felony robbery charges. I guess she was out on bond and was trying to pretend like nothing happened.

Yep he broke it off right there. Armed robbery tends to do that.



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 think 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 but never bumped into each other.

That guy is my husband now.



Met a woman for dinner after chatting online for a few weeks. She's super cute, conversation is flowing well, really hitting it off. I'm talking with 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.



First time going to my now-fiance'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, "'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 laying 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.

TL;DR - Impromptu trip to his place reveals a clean apartment; I turn down his advances because he's absolutely piss drunk; he sees my rejection as a good decision on my part. KEEPER



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. Ive 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. Im 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 Im now confident enough to date a taller woman. So glad I went on that "friend" date!



Just before the second date with my now girlfriend.

She called me to let me know that she was feeling pretty sick (coming down from a migraine + bad cold) and didn't feel up to making the date.

She called me. When, after almost 1.5 years of plugging away at the online dating scene, pretty much all of the ladies I'd gone out with would just pop a text/message on POF/OKC my way.

The fact that she actually called and spoke to me almost shorted out my brain.

We've been together about 2.5 years, been living at the same place over 1.



i never have chased love in the past couple years, 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 cause 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.

edit for clarification: we started "talking" about two weeks into knowing each other, dating after one month of "talking".



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.



Went to a family party and was introduced to my cousins girlfriend. He's about 10 years younger than me and someone I used to babysit. At the party I reconnect with the cousin and he mentions we should go catch a movie together. His girlfriend hands me her phone to put my number in. A few months later she invites me to a movie and I say yes assuming this was the both of them.

Instead it turns out to just be her and she's definitely dressed for a date, tiny purse, heels and everything. I ask where my cousin is and it turns out he joined the military and shipped out and they decided they would both be open to other relationships while he was gone. I ended up watching the movie and having dinner with her but I didn't give any impression that this was a date. Her last effort was to offer to drive me to my car despite her car not being that far from where I was parked.



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. First thing he told me was that he was so high 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 begining though.

Later his brother got raided and arrested right next door because another neighbor called the police after she heard a fight.



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 goto 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 alot'. Erm...


Just out of interest did this charming, cousin kissing individual manage to get a third date and if so did he have any more fun phrases for us?


Unfortunately, his charm and wit didn't persuade me enough to ask for a third date. Shame.



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.


Pretty sure my fiancee never expected to end with a country type guy like me. I'm probably about as far as you could get from what she expected to ended up marrying. She's a posh, artistic, British dancer, and I grew up in a one light town in the middle of nowhere. Tbh I never would've believed I'd end up with her either but I thank my lucky stars every morning that I have.



Casually flirted with a girl for 1-2 months, asked her out, she said yes. On the way to the bar she makes a highly suggestive comment about how she would look in a very sexy dress we see in a store. I think to myself "this is going great". We enter the bar, sit down, things turn around just like that as 1 minute in the conversation she grows completely cold and says "I'm at a stage in my life where i do not want to date anyone".

After 20 seconds dead silent, i replied "Then what the hell are you doing here with me, on a date?". Can't remember the answer but it was something nor here nor there. And it wasn't one of those FWB things. Finished my drink, escorted her to the meeting point, never heard from her again.

Maybe it isn't one of those "Whoa" moments, but the switch from "really cute girl, shows signs she's into me, this could be something great" to completely and utterly cold definitely caught me by surprise.



Went on a date. It seemed to go well. Set up a second date. Dude cancels on me because he wanted to pursue someone else. Alright, fine, whatever. Then three months later sends me a friend request on facebook. I accepted because I was curious. He hasn't attempted to message me or comment on anything. I'm so confused.


Dude is playing the long con. Knows a reasonable person would think its ridiculous to try after that, so he's not. Instead he is biding his time and looking for an angle to make it more "natural"... Either that or he thought you were really hot and was hoping you'd have some vacation bikini pics on your profile... Either way he must have missed out on your obviously superior hotness.



When I was in high school, I was a hostess at a restaurant, and there was a cute busboy I worked with. Eventually he made a move and kissed me after work, and we started casually seeing each other.

One day after work, he pulled out his phone and flipped it open (good old mid 2000s!) and his wallpaper was a photo of a baby. I asked if that was his little sibling and he said "nah, that's my son."

The busboy was only a year older than me, so I was really shocked. He told me that he still tried to get along with his son's mother, but she'd cheated on him so it was hard. My dumb seventeen-year-old ass was like, "yep, I can do it. I can be a stepmom!"

Then I found out he was actually still dating his baby's mother. I let him know that I knew, and he begged me to give him a chance; he said he'd break up with her, that she was really awful, that I could "change his life". I just instant messaged him, "I'm going to block you now," and then did so. Probably the most self-possessed I've ever been with a romantic partner, lollllll.


Kudos on being capable of such a sensible reaction at an age when many of us did stuuuupid crap in the name of love.



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 f**k off 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. Ya. 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.



About 9 years ago I was talking to 2 guys called Angus on online dating. One of them asked me out and we agree to meet at a coffee shop the next week. When I get there I see him and he is waiting tables so I walk up to him and he gives me this look like he knows me. He asks me "table for one?" and, extremely confused at this stage, I reply "umm table for two?"

So I follow him and sit down at the table and he goes to get water and I'm thinking of all the ways I can explain how I'm really unimpressed that he would invite me to the place he works while he's working for our date. As I'm deep in this thought I see someone else approaching my table and it's...the other Angus (let's call him Angus 1). Angus 1 and I had unknowingly organised a date to the place the other Angus (Angus 2) worked and then I'd seen Angus 2 and confused my Angus' and assumed I was meeting Angus 2.

So Angus 1 and Angus 2 arrive at my table at the same time. Angus 1 says "Hi it's me Angus 1 from (generic online dating website)". At this point I can see in Angus 2's face that he's figured out where he knows me from, then he takes in what Angus 1 has said and then gives me a look that literally says "what is this girls weird obsession with guys called Angus!"

To make things worse Angus 2 was a very attentive waiter who checked on us frequently and got to hear the awkwardness that is the first date from an online dating website conversation all while poor Angus 1 had no idea what was happening and probably recounts this story as a date he had with an extremely awkward girl who's weirdly shy and doesn't like to talk in front of waiters.

In hindsight I wish back then I had the confidence to tell Angus 1 what was happening and laugh about it but it didn't happen! Needless to say I never heard from either Angus again.



The summer before I went to college, I ran into an ex at a party and we ended up having a night together.

Sitting in class taking notes a few months later, I get a facebook message from the ex. "I'm pregnant".

Well, now I'm freaking out. I was already seeing someone new, really didn't want a life with this girl, and had just started college. I wasn't ready for a kid. I started prodding a bit, like "what do you plan to do" and "have you told anyone else?", and she gave all the answers I didn't want to hear. Family knew, she was keeping it, etc.

This dragged on all day. I'm freaking out, trying to figure out what the hell I'm going to do about it.

Then, late that night, she mentions she's still in the first trimester.

That doesn't add up, I haven't seen her in like 5 months.

That's when she finally mentions that her new BF knocked her up and she just needed someone to talk to about it, and figured letting me think it was mine was the proper way to go about it.

Never shared another word with her.



Went on a date with a man. Seemed really decent, and I liked him. But then he ghosts me for a weekend. I was super confused, and finally said screw it.

He text me on Monday morning to explain. Told me he has a daughter, who is 2, and he had her for the weekend. Okay, cool, whatever. I like kids.

But then he tells me he's living with a girl that he WAS dating, so I can't come to his house, ever. And the daughter wasn't from her. It's from a co-worker that he had an affair with, so that's why he kept it all from me.

We went on a couple more dates, but then he let me know that he was still with baby mama on the side, and he wanted to try a relationship with her. I said good bye and don't talk me to again.

Less than a year later, they're married, new baby, and guess who is texting me to be his side piece?



Was talking to a friend of mine, just hanging out in the garage. I had been slowly falling for her for a little while before this so one day I just said screw it, told her how I felt. You miss 100% of the shots you don't take. She told me she felt the same way so I went in for a kiss.

This girl straight up mounted me.

We've been married for almost a year and I couldn't be happier. Life is dope.



Met this girl in college. She sat in front of me, so we'd chat from time to time. Semester is coming to an end, and I decide to ask her out. We go get dinner after class, just to get to know each other. As we're at dinner, she starts talking about her kids. plural. This has never been brought up before. I ask about their father(s). She explains it's by the same guy. I ask if it was planned. She responds "Nah, his pullout game is just weak". I pause, and let this sink in. So it happened not once, but twice? ok. I ask about contraception. "It's against my religion, and what kind of example would I set as a youth pastor?"

There was no second date.



This was almost three years ago now. I met a girl online, went on a first date, hit it off pretty well. She invited me to come over her house a few days later as she was gonna have a few friends over. I show up, find out that it's actually the birthday party of one of her friends, a little weird, but okay .

She was from the Ukraine, and everyone who showed up was from Russia or Ukraine, or their significant others. There was a also child. Basically like being invited to a family BBQ as the second date, and by the way, OptimusPyne is the one in charge of grilling for everyone.

At one point one of her friends did the basic, "How'd you guys meet/ how long have you been seeing each other". I told her, she said "It must have gone pretty well". I could only respond with "I guess so?".

Everyone wanted well done burgers. Nice people though.



Dating a guy who was so nice I wasn't sure it could work because I'm kind of abrasive when it comes to dealing with things(not a fan of bs in people skills suck) and I had dated my fair share of people who seemed nice and turned into nightmares. Anyway, he tells me he loves me after the second time we've slept together.

Had no idea it was coming, super worried because the too early confessions of love are usually a red flag. I tell him it's too soon and I only say that stuff if I know for sure I mean it. Fast forward to now, we're married and it's the healthiest relationship I've ever had in my life, not a red flag at all. Just an extremely genuine person who knew his own heart.

It was one of those rare times in life that everything just fell into place. Our schedules matched up, we never ran out of things to talk about, he was and is this singularly kind individual. By the time we actually had bumps, we were so close we just kinda fell into this routine of facing each problem side by side and solving it together. I've been married once before, for eight years of chaos and abuse. I know what dysfunctional dynamics look like. This time around, my husband is like shelter in a storm. What they say is actually completely true. There's nothing like the adventure of finding the right person.



I went to fourth date with a girl..

Ended up seeing her whole family, and slept overnight there.. also helped with farm stuff at morning a bit(i liked it btw)my non-confident ass really did not see that coming.

Not to mention, she called me her boyfriend also.



Background information: When my abusive ex boyfriend and I broke up I was basically packing up everything he gave/let me borrow over our 3.5 years together (3 items total, only wanted one back) to give him the next day with my now boyfriend (the man who gave me the confidence to leave). While packing I realized that my 'promise' ring, that I actually sorta begged for, was on my hand. I LOVED this ring, not for sentimental reasons but because I personally picked it out and it was basically my dream wedding band. I loved this ring so much I broke down crying, it almost physically hurt me enough to get rid of it and my now boyfriend was very aware of this.

The morning my boyfriend picked me up he had a bunch of rings on his hands when he normally ever wore one. I questioned why and he simply stated that the normal ring he wears to work, where he handles food, it's the only one that doesn't slip off. This was only the second time we hung out together so I didn't think to much of it. I had work later that afternoon so naturally he dropped me off. While waiting for my shift to start, sitting in his Jeep, he lays his hands flat out in his steering wheel and says to me,

"Until I can buy you an actual ring you can wear any of mine, take it and it's yours."

He fully planned ahead that he was going to give me one of his rings to wear so he wore them all so I could pick my favorite. I'm still in 'awe' at how sweet it was.



When I was 19 I worked at Buckle in a mall, a few times this gorgeous girl came in. Second time I recognized her as soon as she walked in, let me reiterate, B-E-A-Utiful and I decided I could not let this opportunity pass. Mind you, I am not great looking, average at best. But I attempted to shrug off doubt and talk to her. The moment we started talking, I realized that not only is she one of the prettiest girls I'd laid eyes on, she was intelligent and witty, I was stuck by this even more so than her looks! We talked and she told me she works in Hollister.

Soooo not long after, I made my mind up I was going to do something out of character and stroll right into Hollister and ask her if she'd talk her lunch with me later so we could talk and get to know each other. She agreed cheerfully and told me that 2 days from then would work best since it was a full shift. I was electrified, I was so fricking happy I practically skipped through the mall back to buckle! I probably had a sh*t eating grin for days. I had never really put my self out there and absolutely felt that she was out of my league. So this was exhilarating to say the least.

The next day on the way in to work, she was out side smoking I said hello, we chatted and we went to work. The next day all is well, she texted me, we planned a time and we followed through.

So the break starts:
She asks "Hey do you wanna go smoke really quick?"
I said "Sure, why not."
So we went out and each smoked 1, then went in to go get a bite to eat. We are standing in line, she looks a little pale,.
I asked "Hey, is everything okay?"
She replied "Oh yeah, I just feel a little light headed"
She preceded to tell me "I don't really smoke often and rarely a whole one, I saw you smoking the other day so I figured that I would ask you to go smoke"
Laughing I told her that I only agreed because I saw her smoking and that I really only smoke with other people, if at all.

We got our food, sat down... As soon as we did, her eyes got HUGE, she covered her mouth with her hands and puked. Not just like a little mouthful, she puked. I may have wasted a literal second, but I got up quick and got handfuls of paper towels to clean up. She was mortified and I could tell. I tried to let her know that I really didn't care, stuff happens and I just tried to be relaxed about it.

She cleaned herself up, our breaks were over and we went back to work. She never responded to my texts, avoided me in the mall, and we never spoke again.

I have to say though, for that very short time I knew her, I really liked her personally and found her immensely charming. But alas, I guess it was fated to never be.

So let this be a warning, don't smoke before you eat. Hell, just don't smoke and you'll be fine. Also, I have the worst luck ever with dating.

Maybe one day we'll meet again and I'll have a real shot! But I doubt that possibility.



The moment where I realized that the girl I'd been hanging out with off and on for about 3 months thought we'd been dating the whole time. She was a great person, but I had no romantic feelings toward her and I'd just been hanging out with her as a friend. Apparently she thought we'd been dating. Yikes.


I've been the girl in this situation. It sucked. :(


Yeah, I definitely felt really bad for her, and I basically just apologized profusely for not catching on. :(



I had been dating this girl for a couple years before she moved in with me. She got fired for no-showing there months later, began wildly stealing my credit card to use it, got angry and abusive (emotionally and physically) when she learned I cancelled the card. She stated she refused to look for a job because I am "supposed" to take care of her, do all housework, and everything while she played WoW. That was the first and last time she hit me. Threw her as out that minute.

Prior to moving in, she seemed ambitious, hard working, responsible, incredibly nice but according to her parents, that's only when she's living alone. This flip happened every time she moved in with a guy or her family.



Was secretly dating this girl for a few months as she wanted to keep it low profile and not reveal to anyone yet. 1 day, a guy i knew was telling me how much he fancied her until he found out she was engaged, and the wedding was in the summer. The secrecy all made sense now but what made it awkward was that i had actually met her husband-to-be a few times, we're not friends or anything and he's a really nice guy but he was absolutely clueless about it.



I was dating a girl for almost three years. She had a pretty serious alcohol offense (DUI + accident) before we met. About a year in to our relationship, she was finally sentenced to a alcohol program. This specific county within this midwest state do not mess around with DUIs and is a VERY strict program. I was living a half hour away at the time. I thought she just had made a mistake before and the county just threw the book at her. I didn't realize she had a drinking problem. She couldn't stay sober and they put her in a halfway house. Even in the halfway house she was hiding it. (She did not drink around me and I had no idea). She became friends with other people in the halfway house.

I was halfway across the country visiting my sister and I received a call from her roommate from the halfway house. Her roommate told me that she had slept with her boyfriend and my girlfriend the night before. She was telling me this because she was angry thinking that her boyfriend was giving more attention to my girlfriend than her during the threesome. Halfway across the country getting that call- ouch



After 11 months of casual friendship my crush told me she had been crushing on me for 8 of those 11 months. Been together for 5 months now and couldn't be happier about life.



Having dinner, it's going good, we are laughing I am ordering more drinks. Suddenly guy pulls up a chair sits down and introduces himself, and she goes pale. He's like "you're not going to tell him your married and you have two kids?"

I'm like so I think this is my cue to get out, I just walked away, she called me later that night if I could go pick her up from her house and give her a ride.



Long distance ex gf told me she was very sick and probably wouldn't live for very long. Of course 15 year old me was very distraught but after a long talk we decided to call it quits and she disappeared off of all social media shortly after. Earlier this year I found her very much alive on Instagram. She even messaged me and played dumb. I was really fucking shook up for a while.



I dated my ex for 3 years. Met the parents, did some traveling, grandma gave us her blessing, yada yada. We both thought we had it on lock... We broke up in March 2016. It was a hard break up, very similar to the experiences I'd held my friends through.

What blew my mind the most, though, was when I had a panic attack as the realization hit me that I just wouldn't be with him anymore, but the life we planned together was gone too. It was so confusing to have the next decade planned, then actually starting to look for places by myself for the next week. The uncertainty hurt more than leaving his side, and I never saw that coming. Maybe I knew all along that he wasn't the one. IDK.



Uh I didn't even know I was going on a date. So a friend from college invited me to go to the club/bar with him with a few of our college friends. After much convincing I say yes since it's been a while since I've seen them all. I arrive at the club and text him to come out so he can show me the way to the table. We get there and it's just him and I. So I ask where everybody else is at. He goes on to tell me that they all had something come up and couldn't make it.

Anyways i can't just bail and leave so I get a drunk and he gets a few drinks. Now, he's really shy, but the alcohol made him a non-stop talker and goes on to tell me that he wants us to be roommates and move across the state to start our careers tells me that we could be living in the city and have the time of our lives. Anyways so it's time to leave and I get in my car and he hops on too, and he's drunk so I can't let him drive. So I take him to a taco truck he eats and I drive him back to his car.

He gets out and asks for a hug, I hug him and then he asks for another hug and leans in for a kiss, and I dodge it and he hugs me tighter. And then I finally leave. Never again do I wanna go out with him. He ended up asking me to go out with him again a year and a half later. Clearly he didn't get the memo



Okay so, I might try to summarise it xD Just second year of my degree, trying to fit in and get to know people around the campus I meet this girl; black, really curly hair, shy at first but as chatty as someone can be when you get to know her. We are both interested in art, so we start a club together, hang out and all. I have to admit I have kind of a crush in her, but here it comes, I find out she is ace (No sexual attraction) and prefers girls. No probs, she is a great friend!

Two years later we are real close friends; go everywhere, hang together often, we know pretty much about about and support each other. We keep running and even have built an awesome art community around our first club, met a lot of awesome people along the way... Well, you know, just life. One day just joking, I have these pajama pants whose waistband has gone loose and constantly fall, so I tell her something along "Damn, you're so hot my pants drop on their own". She immediately answered flirting. And not joking but REAL flirting.

I'm surprised but play along, and we spend the next two weeks or so like that, flirting back and forth. We asked each other out, like, one night after going out with some friends, at the same time, and we have been dating for the last eight months. So yeah, like, I couldn't have seen it coming at all, but I am really happy we both took the step! Ah, and we literally skipped through the get-to-know-each-other phase.


How do you handle the ace thing? I am curious.


Well, seems like she discovered she is demisexual instead (Means that only feels sexual attraction if already feels emotional attraction). In many ways for me it was like meeting a new person in her, and I feel like she discovered many things about herself as well in these past months, so I'll be fully supporting her.


That's very nice man. A new journey for you two. Hugs for you both.


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