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Hilarious Stories of First Dates Gone Awkwardly, Horribly Wrong

hilarious stories of first dates gone wrong

Hilarious Stories: First Dates

With Valentine’s Day just around the corner, Hallmark cards flying off the shelves, and couples making plans to get their romance on, anyone would think that finding a life partner is a walk in the park. Well, maybe for some it is, but for others, dating experiences can flit between interesting dinner dates, awkward coffee meet ups and well…the downright weird and embarrassing.

We’ve gathered some of our favourite giggle-worthy stories of first dates gone awkwardly, horribly wrong.  Enjoy.

I was a young man and recently moved out to a city, a fair distance from my hometown. While in town one day I bumped into an old friend from school. She was the year above me, very popular and the one who the guys all had a thing for. Neither of us knew the other lived here, we chatted for a bit and exchanged numbers.

A few days/weeks (can’t remember) of texts back and forth and she asks me if I fancy going out for a drink. Wanting to impress, I decide I need to pick up some fancy new clothes for the date. For whatever reason I don’t get round to doing this in advance, so end up making a desperate dash round a few shops on my lunch break of the day of the date. At the end of my working day I quickly slip into my new outfit and go the bar where we’d arranged to meet.

She turns up and we start chatting. Early in the conversation she says “You look nice. New clothes?” “These?”, I reply. “No, had them for ages.” Trying to play it cool.

The night continues. She’s regularly looking at me, smiling and giggling. I’m sure that my witty conversation is working wonders.

It’s late now and she tells me she needs to get home. Being the gentleman I am, I offer to walk her to the bus stop. As we stand on the platform she’s still grinning and chuckling away.

The bus pulls up. “One thing before I go,” she says as she leans towards me. I close my eyes, believing I was about to receive a farewell kiss.

I feel a pull around the back of my collar.

“Remember to take the tags off your new clothes before you go on a date.” She tugs sharply and not one, but two clothes tags come away in her hand.

She jumps on the bus and pulls away, waving goodbye and laughing hysterically.

Reddit user: munkimatt


I was seeing/dating this girl I worked with and had plans to go for dinner and drinks on a Monday night after work. Mondays at work consisted of me starting at 4am and doing a stock take, taking in the delivery and the finalising stock. On a good day, finish by 11am. This day however, I finish at 6pm.

Anyway, so I finish and have a miserable beer in the bar down the street, then meet the girl. I. Am. EXHAUSTED. But I like her so I power on through. We sit at a table and start chatting. Our drinks arrive, as does some water.

And then I yawned.

Really loud.

And stretched my arms out. And knocked a potted plant over. That knocked a menu over. On to a candle. Setting everything on fire.

And I am OBLIVOUS to this happening. I only realised when a guy at the next table dumped a glass of water on to it.

She’s laughing. I’m mortified. The guy is looking at me like I’m a moron. I get up to get another drink and I get one for the dude at the next table. Set it down and go to shake his hand in thanks and KNOCKED THE F#$KING DRINK ALL OVER HIS DATE!

I apologise. Offer to pay for dry cleaning and sit down. Mortified. We skip dessert and go home. I’ve never been more embarrassed.

Worked out in the end, engaged to the same girl!

Reddit: dippet


It would probably be my very first date with my highschool girlfriend. She was a cute girl, a year behind me. I was an overweight senior who had never even kissed a girl before. So needless to say I was quite nervous.

I invited her over to my house. I made lasagna (wanted to show off how great of a boyfriend I was going to be). I threw on my best button down shirt, splashed on some cologne and prepared for an awesome night.

Dinner went well and after we retired to my bedroom to watch a movie. She had seen it, I hadn’t so she assured me it would be great. About half way through she even decided to hold my hand. Oh how amazing this night was going to be. I might even get my first kiss.

Then I remember how nervous I was. I had never been here before. I wanted to make a good impression. What if I’m too fat for her? What if I am not a good kisser?

That’s when it started. A familiar nervous grumbling in my stomach. I knew that feeling. I tried to ignore it. But then the sweats came. The cold pre shit sweats. I knew I wouldn’t make it. But the bathroom is across the hall from my room. She will hear everything. “Hey I have to run to the bathroom” I croaked. “Ok I will pause the movie” she replied. “Oh no you don’t have to do that. I will be right back” I quietly begged. “I that’s ok I have seen it. You haven’t” she said as she paused the dvd.

I knew it was going to happen whether I liked it or not. So I went into the bathroom, turned on the fan hoping to mask some of the sound and sat down just in time to unleash a tidal wave of liquid shit that seemed to mock me with every push.

I finished my dirty deed and returned to my room to see my new girlfriends face pastey white and glued to my t.v. screen. We started the movie back up, I grabbed her hand again with my cold, clammy palms and finished up my first date ever. No kiss, only a hug would be found that night.

Reddit user: josh42390


Valentines evening, 18 with first serious girlfriend. Parents out of town so I figure cooking, romantic meal and a film is a good shout. Know she likes asian food so spend hours making a spicy ramen soup, made the stock myself and everything. Dinner goes great, swap little gifts, everything going perfectly. End of meal and there’s no thought of putting a film on, clothes are flying off, push her onto the couch…..heavy breathing, moaning, and then “OHHWWWWWWWWWWW!!!!”, she screams, jumps up and runs to the bathroom where I can hear her crying for an hour or so.

Had forgotten to wash my hands, and from that day on was known as chilli fingers.

Reddit: JimmySham


I am the Queen of awkward and terrible dates. I just attract all the awkward and overly friendly from the woodwork and decide that I’ll say yes when they ask me.

One more recent date was with a guy I’d met off the internet (yeah I was asking for this one). He wanted to pick me up from my house in his car and drive us to wherever we were going. I politely refused and said I’d get the train in, considering I was only two stops away and he’d have to go out of the way to pick me up – also refused cos I’d never met him before and he wanted me to get in his car.

So I meet him. I’m wearing this tight pencil skirt, nice blouse (not showing much boob at all) and these gorgeous heels. The heels were aching a tad, but nothing that wasn’t worth putting up with for AMAZING heels.

We decide to go and get some drinks in a bar and I just ask for a Pepsi (I’d been out drinking the night before and did not need to taste beer or wine again for at least another 24 hours) but I did go “But please don’t let that stop you from having a drink”.

He brings back my Pepsi after spending about 20 minutes at a quiet bar (the place was dead – how in the hell he managed to do that I don’t know) and brings back a Lemonade for himself. I didn’t mention it but he went “Well I was going to have a drink but seeing as you’re on Pepsi that put an end to that – I’m not going to drink by myself”.

So we’re having awkward stalled conversation. It goes for about two minutes then stops and we awkwardly look round. As I’m talking though, I notice he’s trying to ram his legs further under the table. I thought he was just trying to get comfortable so I ignored it, but then I realised – he was trying to get his legs to connect with mine. I don’t mind flirty gestures, but this wasn’t flirty, he was literally whacking his legs further under the table just to make a connection. I moved my chair out from under the table because I thought maybe I was mistaken and he was just trying to get comfortable, but no, when I moved my legs out he moved his out and was trying to rub my legs with his foot while it was still in his shoe. Dead sexy that.

I ignored it and thought that if I didn’t pay any attention to it, then it’d stop. It didn’t.

Now we were talking and although I wasn’t having a terrible time, it wasn’t the best. Kind of like on the Sims when you go on a date and you have to get the meter to the top to have an awesome date? We were like 1/3 of the way up on that Sims meter.

I talk with my hands and so I’m there, conversing with this guy, wafting my hands everywhere like I usually do and I notice his hands reaching up. They were reaching for my hands when I was talking to try and touch them. He was trying to hold my hand but wasn’t being very subtle or smooth about it. It was like he was mini high-fiving me for the entire conversation.

By this time I already knew I wasn’t going to see him again, he was too touchy and quite frankly I’m not. He suggested we go somewhere else and I almost agreed, until I went to stand up and HOLY F$#KING SHITWITS WHY DOES MY FOOT PAIN SO?!

Turns out my beautiful heels had given me a beautiful blood blister – yummy. I couldn’t walk, I just couldn’t. I kinda made my excuses about leaving because there was no way I was walking ANYWHERE and then thought “Fuck it, I’m not seeing this guy again, might as well take my shoes off”.

Took those heels off and walked outside the bar with him. He offered to walk me back to the train station, but Lord knows I wouldn’t have made it. I told him I’d phone a taxi and thanked him for the lovely night. He then offered to give me a piggy back to the station. After careful consideration for a good 5 minutes I refused – I was in a pencil skirt remember and everyone would have seen my knickers.

So as we stood and waited for my taxi to pick me up, he’s edging closer, trying to kiss me. Erm no. No. So I edged away. We ended up about 50 meters down the road from where we started off because he was trying to get close to me and couldn’t read the body language that I REALLLY did not want to.

Next day he asked me out again – politely turned him down and he went all crazy over text asking me what he did wrong. I just said that I thought he was more into me than I was into him and despite having a good time I didn’t think it was fair on him to do it again because I wasn’t that interested.

Tl;dr Date was too full on; tried touching me at every opportunity; I got a giant blood blister and took my heels off; he offered me a piggy back; did not take it.

Reddit: neenoonee


She pretended to be a photographer so that we would seem to have common interests. The date was a photo walk in a public park. She couldn’t find the ‘on’ switch on her camera, and kept it on green square the whole time. Halfway down the boardwalk she exclaimed “I have to pee” and immediately squatted behind a bush, still in plain sight of the hundreds of other people in the park. I almost left her there, I was so embarrassed.

Reddit user: Christof3


I went on a blind date where we were to meet at a restaurant. I waited in the bar for almost and hour before I left. He texted me and begged me to come back since he was stuck in traffic, it was feasible so I did. When he finally arrived another 20 minutes later, We began to have conversation and no less than 50 times in the next hour he told me that I was having a good time. I’m not sure if he was practicing the art of persuasion or planting subliminal messages. At one point I actually said no, I’m not really having a good time and he laughed and said yes you are. I cut the dinner short and as soon as I got in my car-he texted to ask me for another date since we had both had such a good time…

Reddit: Poopscoopmagoo


First date I called her the wrong name. Second date I lit her hair on fire while trying to be smooth and light her cigarette. Six years later we’re happily married. Don’t count out the bad dates.

Reddit: Dorpher


Have you had a weird/funny/embarrassing dating experience?



Jolene enjoys writing, sharing and connecting with other like-minded women online – it also gives her the perfect excuse to ignore Mount-Washmore until it threatens to bury her family in an avalanche of Skylander T-shirts and Frozen Pyjama pants. (No one ever knows where the matching top is!) Likes: Reading, cooking, sketching, dancing (preferably with a Sav Blanc in one hand), social media, and sitting down on a toilet seat that one of her children hasn’t dripped, splashed or sprayed on. Dislikes: Writing pretentious crap about herself in online bio’s and refereeing arguments amongst her offspring.

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