The Most Epic First Date Break Up
The Most Epic First Date Break Up

Diego Cervo/Shutterstock

I'm familiar with the area so no big deal.

We walk in and her family is celebrating her aunt's birthday. There were only family and a lot of it, about 40 people. She introduces me and everybody was happy to meet me and really nice. Everybody also knew that she was out on a first date. They were asking her stuff like, 'Is this the guy?' 'Is this your date?' 'Is this the one?' All of the sudden I wasn't so cool and relaxed. I felt heavy pressure to be on my best behavior. It was high pressure to the 3rd degree.

We sat down and I started being questioned by her older sister, her aunt, and another lady. Her mom started kind of defending me and telling them to back off and let me eat. But the interrogating continued. After I don't know how long they turned to my date and jokingly said: 'We approve.'

I was totally off balance all night, just tense. I was afraid the back of my shirt would get that a big wet spot cause I felt sweat. Later the sister brings her cute little girl and lets me hold her and she and my date started taking pictures of me holding her, and somebody else's baby boy as well. I started to feel like the tone of it all was that we were a couple. I kind of felt like I was married to her and these people were my in-laws.

After a couple of hours, everybody was kind of tiring out and everything began to wind down. Then her dad suddenly asks me 'jokingly' what my intentions are with his daughter. Everybody at the table looked at me which is about half the people there.

I guess I was exhausted from all the questioning (I was questioned by multiple people, multiple times) and the pressure of it all cause I kind of lost it. He asked the question, I looked across the table at her, and she told her dad to stop it. Her dad smiles and jokingly says that he'd really like to hear my response, and her uncle also said he'd like to know (jokingly). I looked at my date and said, 'Can I talk to you alone for a minute.' To which her dad laughs loudly and says: 'I made him nervous.'

So everybody is laughing and I guess it was a big joke. Then her sister says, 'Oh there are no secrets in this family, speak your mind.' People then laugh again and everybody starts making jokes about not having secrets and this man who married into the family somehow tells me that he remembers being in my place and he says, 'Let me give you some advice, the best thing to do right now is speak your mind and be honest.' Then others join in and echo his sentiment.

So I looked at my date and she says, 'You can tell me anything here, we're all family.' She also I think was joking. But I had started to lose my ability to tell when people were joking and when they were serious. So the dad says, 'Wait, I haven't gotten an answer to my question.' So finally I speak directly to the dad and say, 'I'd like to discuss that with her first.' But I REGRETFULLY, laughed as I said it. So her dad says, 'I asked you first, I wanna know.' I turn to my date and she says something like, 'Go ahead you can tell me, I'm a big girl I can handle it.'

So I said ok and sat down then took a couple of breaths while her dad kind of quieted everybody down. I started with 'I think I made a huge mistake.' It all spiraled down from there. I said harsh things like that I felt like I was having a bad dream where I was suddenly married. I questioned her intentions in bringing me there. I said stuff like, 'What were you thinking?' 'Yes, I liked you, but I just met you, and right now I know your aunt (I pointed at her sitting next to me) better than I know you.' I think she was humiliated but I couldn't stop, the more I spoke the more bad stuff came out, total tailspin. I said I want to find someone special but I don't want to skip the first 29 dates and skip to date 30 which is what I'd done that night.

Then people started interrupting and chiming in and suggesting that she and I slow down and have a real first date. I wasn't having it, I was out of control. I said, 'No, it's too late for that, I feel robbed here, I wanted to meet this girl, get to know her, date her, and maybe fall for her, but now it's like we're engaged and her whole family is here and there are all these expectations. We skipped the getting to know each other, and dating part so I feel robbed.' Then I said yet another thing I regret. I said, 'It's a HUGE RED FLAG (with an emphatic gesture) that I asked for a minute alone with you to talk, and this is what I got instead.' I added something like 'You're all great and a great family, but the lack of certain boundaries is a huge red flag for me. I would never let my relationship become family business.'

My date interrupts me at this point and says, 'Ok, so let's talk in private, let's go outside and talk, I'm sorry I didn't give you that minute, let's go outside and talk privately, I'll give you all night.' She was visibly shaken and I could tell tears were inevitable. I stood up again and realizing that I had insulted all of them I just quietly walked out. I felt really bad cause they were all nice and had nothing but the best intentions for me. They love her, and they were literally telling me that I was good enough which should've been a compliment, but I somehow took it the wrong way and spat in their face. I didn't even drink."

There's No Recovering From This
There's No Recovering From This

mr. teerapon tiuekhom/Shutterstock

"Took a girl to movies (I now realize not the best location for first dates).

She asks 'can my best friend come too?' (there go my chances basically) I say of course she can! (trying to be nice, was also assuming it was going to be a girl).

Shows up with her friend, who is indeed a guy. This is when I find out that it's her one and only ex, but they remained best friends and nothing is happening between them (well this date is ruined, let's try to salvage it).

Go to pay for our tickets (me and her), even when she offered to pay for hers. After buying, she turns around and buys her ex's ticket...

We actually got along fine and they were nice people, but it was like a tug of war for the rest of the night fighting for her attention. Of course, I lose, they are best friends.

When I get home the guy adds me on Facebook, and he proceeds to tell me don't bother trying to date her, she's a terrible girlfriend (thanks for the heads up).

I finally got her alone for one more movie, but it all just sort of fell apart, I actually really liked her, but clearly, I had no effect on her. Oh well, I guess.

Take note future daters, this is a huge red flag..."

The Most Memorable Time Of His Dating Career
The Most Memorable Time Of His Dating Career


"This is hands down the worst date not only that I've had but any of my friends have even heard about. When it got bad that was only the prequel to what was to come...

2003, I'm at home and get a random phone call, let's call her Melissa, is on the other end. She says she got my number from a mutual friend who thought that I would like her. Okay, this an odd phone call but I'm really single and a prospect of going on a date sounded delightful. We talk for more than an hour and she is sprinkling hints as to what she looks like, she also says she has seen pictures of me and thinks I'm cute - bonus! She mentions her bra size more than once, ok sweet I like a bigger chested girl I'm thinking.

We line up a date for the next Saturday, it was Thursday. I live in town and she lives in a suburb that requires her to catch a train and then a bus, roughly a two-hour ride to see me. I have no idea what she looks like, except that she had brown hair and an extra large bra size. I'm standing in the spot where we decided to meet and I'm seeing a girl kind of stumbling down the street, she's wearing those baggy type jeans that goth kids wear, really baggy and frayed at the cuffs, not my style at all. Also she's got way too much makeup on. Turns out it's her. She tells me the reason she was stumbling was due to the fact that she got a bit nervous at the idea of a blind date so she picked up a pint of Smirnoff for the train ride into town, then another for the bus ride and she is now meeting two pints deep and clearly not sober. The second she notices me, her haze rises a notch to a level of excitement and she drapes her herself across me in a sloppy hug with a butt grab added at the end.

I'm confused and scared and nervous and a bit frustrated all at once. I had planned to take her to play pool at an upscale place downtown that's kind of trendy. I mention it and she's all for it as long as they serve drinks, hmm, ok.

At the pool hall, the waitress gets us a table and asks us if we would like a drink? 'Four shots of Jose and a pint of Budweiser' she says. 'Wow ok, Jose? I'm not usually a fan but ok,' I say. 'Oh did you want some too,' she replies. They were all for her. Keep in mind it was probably around three in the afternoon. The drinks come and one after another without a pause goes down Melissa's throat. One shot two shot three shot four and then downs the pint. Upon finishing the pint she looks right into my eyes and wipes the foam from her lips with the back of her hand and my mind pictured what a murderer looks like moments before committing an act of horror. She saunters over to me while I trying to line up a shot and says:

'You can take me. We can go to the bathroom right now if you want.'

I miss my shot partially due to the hand creeping its way to my crotch. I kind of laugh her off and say maybe we should wait until we finish the game. She lets out this impatient sigh and grabs my cue to make her shot. She isn't really lining it up and then she takes a hit. It barely even grazed the cue ball. In frustration, Melissa throws the pool cue across the pool table whereupon hitting the carpet snags it and creates a massive tear across the table. This is hilarious to her and she starts laughing like an idiot hyena. I'm less than amused. I say I need to take a leak and head to the bathroom. I'm keeping an eye on my back as I do in the case shes tailing me. In the bathroom, I lock myself in a stall and put my face in my hands. How did I get here? Who is the woman and why did I agree to this? How can I get out this? Where is my god and why has he forsaken me?

While I'm in the bathroom contemplating my poor life decisions I'm hearing a commotion outside. Some sort of shouting and a glass breaking. I compose myself as best I can and leave my sanctuary.

Melissa and the bartender are face to face yelling at each other. The bartender is being rational and asking her not to pull at the tear created by her pool cue lancing. Apparently, she thought the hilarity would continue if she ripped more carpet off the table while the waitress and bartender thought better. Melissa sees me and starts explaining how much these two are idiots. I try calming her and tell her maybe we should hit up another place anyway. She complies. There seems to be a God after all.

I'm an opportunist so I try to make the best of this situation. I'm mentally crossing off the date stuff I can do with this girl in her inebriated state and come to the conclusion it would be best to just drink and pass the time until her scheduled bus leaves. She's all for it, surprise surprise.

I grab a 12-pack and being a sunny day I suggest a beach not far from the train station. I've stated more than once now that she should be on her way when the bus gets here, I didn't want her to have to be stranded in town if she did, I say. She reluctantly agrees.

We pass the next few hours drinking on the beach, and her trying her best to paw at my crotch. By about six thirty or so I'm fairly buzzed and not far from ending this odd scenario. It's about time to head to the bus station and she's moving at half speed now and hinting that she doesn't want to leave yet. I'm not paying attention but instead taking her by the elbow and inching toward her bus. She doesn't have any more money, I pay for the ticket. The bus driver takes her ticket but she doesn't get on. Instead, she looks over her shoulder at me and then proceeds to empty her stomach right on the first step of the bus. The bus driver pushes her back, curses her, closes the door and peels off. Oh god no.

Wiping her mouth of leftover vomit, she gives me a faint smile and says 'Well looks like we can hang out a little longer.' I'm not amused and I'm not trying to hide it either, I'm not smiling, I'm not being polite - I'm a totem of disappointment.

I'm walking away from the train station with her in tow. She explains that she has nowhere to go and it really isn't a big deal if she just goes home with me, and besides, we can have some fun while we're at it. No.

I let the steam of anger simmer down a bit and think logically she really doesn't have anywhere to go and it would be a bad move to just leave her to her own devices (mistake). Reluctantly I tell her she crash at my place, but its gonna be on my couch. She's all for it.

I live with my cousin at the time and he's home. When he sees this atrocity come in behind me he runs to his bedroom stifling the laughs along the way.

We watch a bit of tv while finishing the last of the 12-pack. I tell her it's getting late and I'm gonna call it a night. I grab some extra blankets and pillows for her. She takes them quietly and thanks me.

Then in the middle of the night, I'm awakened by a sensation that I'm being crushed. Melissa is on top of me, our faces are inches apart.

'I couldn't sleep.' That was all she said.

I tell her to get off of me and that she's hurting me. She gets up. She says she didn't want to sleep in my living room and asks if she can sleep in here with me. Wordless I get up to grab the blankets and pillow from the living room and make a bed next to mine. She watches me do this and when I finish, instead of saying anything I point to the bed and climb back into my own. Once more that night she attempted to get on top of me. Also, she never took her shoes off.

The heavens smile upon me by blessing me with daybreak. I wake her up and repeat the process of taking her to the bus station. This time the formalities are gone, there's your bus don't puke this time, no I didn't have a good time, but goodbye anyway.

On returning home I pull out my black book and look up our mutual friend, and proceed to rag her out for putting me through such an ordeal. My friend is perplexed and has no idea who Melissa is. I describe her and there's a moment of silence. She says she remembers now. My friend had her friend from out of town come to visit but she had brought along her cousin who was high functioning but a special needs student. Her mother was in the process having her signed over to a group home here in town. When Melissa visited my friend she apparently went through her things and found a photo of me with her with my phone number on the back and took it.

I went on a date with a mentally disabled woman."

A Total 180 Flip That He Never Saw Coming
A Total 180 Flip That He Never Saw Coming

Damir Khabirov/Shutterstock

"I'm walking down the street just finishing a conversation on my super old, craptastic, flip phone. Just as I'm hanging up, wham, I knock into someone and drop my phone. I apologize, grab my phone, and head back to work.

Ten minutes later I get a phone call: 'Hey, I think we switched phones by accident.' Turns out the girl I bumped into had the same phone as me. Anyways, we plan to meet at a local coffee place after work that day to trade back. I walk up and see this very cute ginger wearing a suit dress. We chat for a bit: turns out she works at a bank, likes what I like, and is totally up for getting dinner this weekend! Great!

Saturday evening rolls around and I swing by her place to pick her up. Out her door walks a girl who looks remarkably like said date only instead of professional office clothes, she is wearing 4-inch platform boots, fishnet stalkings, some sorta corset-like top and spiky hair.

Now normally I don't really care about a person's style, but I was bit taken aback. 'Who cares' I think and jump out to open the door.

Cue witty banter.

Everything is going great! She's laughing at my jokes and her humor seems to match mine perfectly. She asks what the plan is for the night and I tell her I'm going to take her to my absolute favorite high-quality dining establishment... and get her a Big Mac. And, if she plays her cards right, I might even supersize it. She runs with the joke, and even one-ups me. My spirits are high. She might have wild fashion, but this chick is cool.

We arrive at this nice pub in town and I turn off the car.

'What about McDonald's?' Legit confused look on her face...

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