What is the strangest way you’ve ever been asked out? Share your wild dating stories! #weirddates #datingfails #funnyflirting
Have you ever had a truly bizarre approach to dating?
Have you ever experienced a dating proposition that left you scratching your head? Maybe someone used an unusual pickup line, or perhaps they put on a wacky performance to capture your attention. Share your weirdest dating encounters with us!
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Join the conversation and connect with others who have had similar quirky dating experiences. By sharing your stories, you not only entertain others but also create a sense of camaraderie. Who knows, you might even pick up some tips on what NOT to do when asking someone out!
Don’t be shy – spill the beans on the weirdest ways you’ve been approached romantically. Let’s turn those awkward moments into amusing anecdotes that we can all enjoy together. Let’s get talking!
I had a guy come into a restaurant I worked at right before closing that I had never seen before. He was cute but he just looked off. He was looking around like he was really nervous. This guy came right up to me at a table and said “I think you’re really pretty. Would you like to go out with me?”
I probably looked confused af when my cook came over armed with a broom lol, we were the only 2 in the restaurant and she’d gotten the same weird feeling, so she came over saying “we’re closed”.
The guy bolted and I never saw him again. My cook and I for a while were both convinced that his intention was to rob me or something, but how funny would it be if it was just a really nervous guy 😂
Dude made a facebook event and only invited me. I didn’t go.
Grown man sent his elderly mother over to ask for my number
One time in middle school this boy had a crush on me but was apparently too shy to ask me out so he got his friend to ask me on his behalf 😂
Another time when I was 19 and working as a cashier, this middle aged woman was trying to get my number because she wanted to set me up with her 24 year old son, who wasn’t even there. Like I’m newly 19 and this random woman who I’ve known for 2 seconds is already talking about what a good wife I’d be for her son and good mother to her grandkids 😳
grown man asked me out to the movies through work email
Guy at school bullied me so badly to the point I had panic attacks on the day I had lessons with him. Proceeded to ask me out years later because he bullied me because he liked me 💀
“I remember a little while ago you said you would be interested in playing that game I sent the soundtrack for, so would you like to hangout sometime to play it?”
The message that my now boyfriend sent me over Discord when I was literally across the plant trying to work up the nerve to ask him out myself, and I let him know flat out that he beat me to it when we went on our 10 minute break soon after.
As for the game, it was Guilty Gear Strive, and my main will forever be Testament for that game in the Guilty Gear series.
Drunk guy at a bus stop asked me to move in with him because “you look Irish and seem nice.”
When I said no, he offered to marry me first if that was the problem.
When I said I was already in a relationship because I was at the time he said “Oh. Well. If it doesn’t work out…”
So since it didn’t I guess I could always go find drunk bus stop guy, maybe he’s still waiting eight years later.
I was trying to get a latte after work at a Starbucks. He was working the register. He kept trying to get me to engage by teasing me. When I didn’t respond, he said “Oh! You’re one of those meek and meager types!” Then when he gave me my latte, he told me “go sit outside now.”
I was confused but also drained from a long shift, so I did it. He took his break and came over to talk to me. I couldn’t even tell he was hitting on me, until I mentioned being new in town and how it’d be nice to make a new friend, and he said “yeah fuck that, I have enough friends.” Instantly put me off.
Rando at work, asked me to make time for him so we could go on a date. I barely know ANYTHING about this dude. When he walks in my office he just stares like I owe him money. And walks pass without acknowledging my existence lol
In some of my first jobs working as a waitress or cashier I got asked out a fair few times. It’s always awkward because I just wanna get on with my shift and go home. After declining it’s not like I can just remove myself and they didn’t always take no for an answer.
Online the weirdest was someone on my mom’s Facebook friend list, who saw a selfie she had posted of us when visiting me and felt inclined to message me with compliments.
Guy came up to me and my mom in the Trader Joe’s parking lot in gym shorts and a tattered tee shirt and asked if I had a boyfriend. NO AND NO. My mom didn’t hear him and thought he was asking for money 😭
I did something weird, I liked this girl in my university class but I never had the courage to ask her out. I once was with a friend who happen to know my crush’s friend, and they were talk together so I was talking to her about my crush she said “You do like her!” I said “Yes” “ehy don’t you ask her out?” ” I will”, my crush knew everything and she was kimd waiting for me to say something, but I never did, although I sometimes talk to her about school related stuff, but I was too scared to ask her out.
Ex’s best friend asked me out on my ex’s phone. Not even a day after I was dumped by that ex. I politely passed.
I don’t miss high school.
My mom told me that when she was in high school. A guy randomly came up to her with a black rose and proposed to her on the spot. She didn’t know him. They were complete strangers.
Idk if this counts but I used to work chat support for a claims management service and one time someone said they wanted to buy me coffee, another person asked for my instagram so we could dm. Mind you they only had my name to go off of.
I look really young for my age. I was waiting for the subway and he comes up to me and asks “Are you a little girl or…?” And I’m like “What?” And he says “Are you like an adult woman? If so, can I have your number?” I obviously say no, train comes in, and I thought he went in a separate car but we awkwardly rode the subway together until I switched at the next stop.
I was assaulted while biking and a delivery driver who witnessed it came up and offered to bike to my destination with me to make sure I got there safely and on the ride he said “ngl you’re gorgeous, I’m not going to do it, but I understand why that guy did that to you. Can I take you out?” I hate men
Guy texted me: my mom said you’re cute and I should ask you out. So wanna go out with me? 🤮
Worse. I recently went on a date and did not realize it was a date. After I sat and ate food, he constantly texted and called. He’d invite himself over (of course not) and ask me to go grocery shopping with him. It was weird. I blocked him.
A guy left a note on my car asking me out for dinner, and an email address. I wrote and asked who he was. It took several emails back and forth before he told me we had met at a club 2 years earlier and he had been looking for me since then. He asked around at the club until he got my full name, address, etc. He asked if I was still with my boyfriend. He finally sent a picture and I remember meeting him. What really bothered me is that no one at that club would know my name, address, what vehicle I drove, etc. so I still don’t know the truth about how he found me. I told him he was being creepy and to leave me alone. He continues to send a message every couple of months asking me out. He’s not using a real name on his email so I can’t report him to the police.
I was at the store waiting in line for the cashier and this guy also waiting in line in front of me made a comment to me about the weather or something you know, regular small talk. Thought nothing of it.
After I checked out and went to my car he followed me like 4 blocks and kept trying to pull up beside me driving into the other lane. Eventually, I had to stop at a stop sign and he made the “roll your window down” gesture and asked me out.
I had a ring on that day and I moved it to my ring finger and said I was married. Uhg what a weirdo!!
Guy was honking and waving his hands at me in bumper-to-bumper traffic. I rolled down my window thinking there was something wrong with my car, but as soon as I did he shouted, “can I have your number?”I laughed and politely declined because I have a boyfriend. He was really sweet and said that I should tell my boyfriend that he was a lucky guy. Seriously made my entire week. Kinda wish I gave him my number just so I could commend his confidence.
i was leaving the airport in LA, which you can imagine has extremely busy traffic. i was waiting outside for my ride and a man in the passenger seat of one of the cars starts yelling things at me and asks for my number. he proceeds to get out of the car, in traffic, and walk up to me. i gave him a fake number just so he’d go away.