37 Hilarious date stories that really happened

37 Hilarious date stories that really happened | Beanstalk Single Mums

Do you want to hear some hilarious date stories?

Modern day dating is crazy, sorry but it is. Meeting people easily online, then heading out to meet them in-person can create all sorts of scenarios. You have to be pretty thick-skinned to put yourself out there as you never know who you’ll come across and what might happen.

The most important thing is to take every first date with a pinch of salt and don’t pin your hopes on anyone until you’ve met-up several times. How people come across online and on a first date is sometimes not indicative of the person they really are. A good way to cope if things don’t go as planned on a date, is to have a damn good laugh with your friends about it. For this reason, we’ve put together a list of hilarious date stories, courtesy of the brilliant ladies on the Single Mum Vine Facebook group.

Names have been left off, but all quotes are exact. Enjoy!

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I had a date lined up with a farmer. Her turned up to my front door to take me for coffee with a huge pumpkin in his arms. He said as a mum that he figured it would be more practical than flowers certainly made an impression.

Sooo I am on tinder, set it up one night when I was drunk, mostly there for shits and giggles now though haha. This guy I matched with when I first set it up reeled me in and I met with him cause he was funny as. We went driving and an hour and a half later he says “okay so if anyone asks I was the best root you have ever had” and dropped me off  I was sooo confused, embarrassed and pissed off course it was a waste of my time. I am still left wondering wtf tinder is really about. I feel like he too is there for shits and giggles and I actually can’t be mad at him because he taught me not everyone is just after a root.

I invited a guy from tinder over to my house for one thing only and when it finally got to that time he lasted one thrust and then says “I told you we should have done more foreplay”, safe to say I didn’t contact him again lol, a couple of months later though I got a message from him just before Christmas of his penis with a bow tied around it and a message saying “hope you like your present”, no thanks mate.

Went on my first date in over 3 and a half years. We were going to a nice restaurant and the guy turned up with old thongs that made sounds as he walked. The sound still haunts me.

I went out with a guy who got SO drunk on the first date. First time we’d ever met. He texted me when I was in the toilet saying that he loved me. He cried at one point. He was literally stumbling and couldn’t even talk properly. I ended up letting him sleep on my couch, because I couldn’t possibly put him on the train in his position. He SLEPT TALKED all night. He randomly yelled ‘FUCK OFF’ around 2am. It was so awkward and uncomfortable. I was really annoyed at the time, but now I actually find it hilarious. He was so embarrassed and apologetic the next day.

I went out with a guy once who purposely did the LOUDEST fart, laughed, and then said ‘Hope ya not sensitive about shit like that’. Well, I’m not sensitive mate but that’s gross. Then 5 minutes later, started telling me about how he called his mum a fat cow when she was bending over doing the weeding. And he thought he was HILARIOUS. That poor lady. Needless to say, no second date for that guy.

I went on a date with a guy from tinder. I had to drive to him because he’d lost his license. He was nice, had lunch and and a wander around then left. We texted afterwards. The next morning though I woke up bombarded by messages saying “why are you still asleep? You’ve been asleep over 8 hours!” And “how’s my little best friend?” (Referring to my son) and “when can we hang out again?” Sorry mate but back off.

My first ever online date lasted 9 hours. My ex turned up and caused a scene. The police came and took him away And then I realised I had no money in my account so had to borrow $150 off the new guy. And yes I did see him a number of times afterwards.

Had a guy ask me to lunch. Seemed nice enough. I haven’t dated for over two years so I thought lunch sounded like a good place to start. We met at an Italian restaurant he suggested. He was wearing all black. Black jeans and black knit with cat fur and little lint balls all over it. (not a good look but looks aren’t everything right?) We sit down and he proceeds to tell me he is friends with this gangsta guy, and this drug dealer guy, and this underworld figure and this other person in jail… and so on and so forth for approx 45 minutes non stop. It was never ending and I couldn’t get a breath in bewteen his rambling. Majority of the names I had never heard of and the few that sounded familiar I’m sure were from some underbelly series. Trying to change the subject I asked what he did for work and where he was living? He then tells me that he is sleeping on his mother’s couch as he is on parole for drug offences and being a “career criminal” (his words) he refuses to ever work in a position that he is required to pay taxes because “fuck the system” (again his exact words.) He then finishes with “Anyway, im goin back to jail next month for an armed robbery me and me mate did a while back so I’m just looking for a regular root before I go back if you’re keen?” I told him i had to go as I had to pick my child up from daycare by 1pm. I asked for the bill. He then casually throws a $20 bill at me and says “Thats all I have right now but you’re sweet with covering the rest ay?” I quickly paid the remaining $60 without a second thought and high tailed it out of there. He was blocked before I left the car park.

I was asked to smoke weed and go to Timezone stoned! I had to make an excuse to cut the date short! Only lasted for 2 hours! Lol.


I’d had a few drinks. We were sitting across from each other. I fumbled around in my handbag to find my lip gloss. I pulled it out and up to my mouth, only to discover it was a tampon.

I used to groom dogs. A lot of men told me they have fleas and matting so I’d wash and groom them.

Had been chatting to a nice guy for a few days. All seemed nice, he seemed normal. Later on that week, I was picking up Thai for myself, and checked my phone to receive … a video of the guy, um, well ,enjoying himself!! Out of the blue!!! Totally out of context, at 5.30pm at night!!!! He had no excuse except that he was horny and thought I’d like the video. Arghhhhh. I have to say I couldn’t watch it. Passed it around to my girlfriends the next day, it provided a great deal of entertainment over lunch.

One guy thought I’d appreciate pictures of him posing naked in bed with his ass up in all the pictures. Was very weird.

I met up with a guy on tinder once. He was lovely and the date was going really well but I couldn’t shake the feeling that I knew him from somewhere. A few drinks in and it clicked. I used to be his beauty therapist and used to do his Brazilian wax! We’re still mates to this day.

One asked me would I meet him at McDonald’s wearing only jeans & a shirt … wanted me to be bare foot … no shoes … obviously had a foot fetish.. I didn’t go lol.

I met up with a guy once from ok cupid. We had chatted online for a couple of hours and I met him at a pub with some friends. He talked for about an hour about mostly himself and his religious mother. Then I excused myself as it was late and went home. On the way I messaged him and said ‘it was nice meeting you but didn’t feel it, good luck with your search’. He wrote a loooooong diatribe about how I judged him without giving him a chance and I was shallow etc. So I wrote back and asked him what my name was (as it wasn’t on my profile) – he didn’t know. He spoke at me for an hour and never even asked my name. He messaged me for about three weeks straight while I didn’t respond after that – think my judgement is pretty spot on.


My 1st and only tinder meet up, he drank all my beers, took himself a 6pack home, and left all his empty bottles on the table when he left. Catchya mate.

I had a guy ask me if I wanted to come over and sit on his face? I said no lol.

I walked up to the wrong guy, smiled and started my flirty moves (coz he was cute), until his girl walked over and glared at me. I went bright red. I think he was just trying to figure out what I was doing so just smiled and acknowledged long enough for me to feel like a goose. The ‘real’ date was way less cute. 

I had lunch with a guy off tinder, he looked nice in his photos but didn’t have any smiling ones, turns out it was because he had terrible teeth and they were yellow from smoking so much. He then proceeded to tell me he was getting his licence back in 6 months so I asked how long he lost it for, 10 YEARS, he lost it for 10 years. Then I had to drop him home to his parents house where he lived (this guy was 30 at the time). He messaged saying he’d love to take me to dinner and I slowly stopped messaging him. About six or so months later I saw a newspaper article that had the same name as this guy, it was him and he’d been arrested drink driving 3x over the limit, speeding, unlicensed, unregistered, uninsured with a lot of cash money on him. He went to jail for five years.

On a date, I had a guy ask me, “So, do you actually like that colour of lipstick?”
Obviously, as I chose to wear it. I was furious and he still tried to kiss me afterwards.

I dated a guy for 6 weeks, he rang me one night to say the police are at his families house, I go why, he says I am an illegal immigrant … needless to say I was very embarrassed … another one told me he was a member of the Ghanaian royal family after knowing him for 2 years … so … hmmm … stay away from Ghanians?

I decided to date women for the first time! A beautiful lady who made custom lamp shades asked me out on a date. She seemed really quirky and interesting, so I said yes. We met up for lunch and half way through a man walked past our table and said hello. He proceeded to sit down with us and introduced himself. He was her fiancee. They were looking to live out a fantasy before they got married. I felt like a complete fool! Ended the date politely and we never spoke again.

Oh oh, my worst date lol told him I was a bigger girl & he says to me upon meeting … you would never know by your face that you were obese … then he rubbed my back, giggled & said oh lol I’m rubbing your fat bits … that was enough for me, I upped & left .. asshole lol

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If you have some hilarious date stories to share head over to the Single Mum Vine FB group, we are sure to have a giggle with you. Or, if you prefer to stay private, share your story on our Anonymous Single Mum Forum.

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Sally Love

About the author

Sally Love is a pseudo single mum author who has been writing about single motherhood, separation and divorce for 8+ years. She has been a single mother for 10+ years and has two daughters, one of whom she co-parents and the other she solo parents. Sally has experienced all aspects of single motherhood from legal, financial, parenting, dating, travel as a single parent, re-partnering and re-building a career. She is an integral part of the Beanstalk community chatting and helping single mothers across the globe, as well as sharing her expertise, experiences and genuine reviews with major national newspapers and appearing on nation-wide television shows.

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