15 People Tell Us Their Best Stories Of Being Flirted With At The Worst Possible Times


The only problem with “meet cute” stories are the clueless idiots who get the idea that there is no wrong time to express romantic interest in someone. This is wrong. We asked our readers to tell us about times they’ve been absolutely floored by another human’s choice to initiate flirting protocols. The answers ranged from “in the middle of divorce proceedings” to “at a relative’s deathbed,” but at least they are all a lot funnier now that time has passed. If you read these and see yourself in any of the flirters, congratulations: you’re probably self-aware enough that it’s not actually you.

1. Deena wrote us this story to remind us that people get divorced for all kinds of reasons. Some of them, though, are obviously because one spouse is a skeeze.

The county where I live requires all divorcing couples with children to attend a kind of seminar about not traumatizing your kids with your divorce issues. This seminar takes place in a courtroom, and is filled with miserable people struggling their way through a divorce.

During a break, the guy in front of me, who had been trying to eye-fuck me since he’d first seen me, turned around and tried to chat me up, while I was sitting next to my soon-to-be ex husband on probably the worst day of our lives.

2. Sean from Facebook was in a gay bar, but was very visibly not having a sexy time when a guy with an advanced degree in awkwardness made his move.

In the bathroom of a gay bar, I was tending to a dryness-induced bloody nose. Some Romeo finishes at the urinal, turns, and drunk-seductively says, “hey, I can help you with that. I’m a doctor.”

3. This email came in from a reader who wanted to remain anonymous for extremely understandable and terrifying reasons. Pay your bills, folks: not just because it’s responsible, but because Repo men are creepy as hell.

*deep breath* So a few years ago my parents usually picked up the bill for my car if I was tight for cash, but apparently they forgot and I just assumed they paid it, so for two months no payment, so the bank sent a repo car. MORTIFIED…. Understatement.

Long story short, I paid in the tow truck. Much to my horror, the tow truck Repo driver went from screaming at me to get out (I thought he was trying to rob me as I was sitting in my car), to flirting with me (can you say petrified/scared shitless?) the entire time I was riding in his truck while towing my car to the creepy deserted car lot to sign papers that I paid, to hacking my BANK FILES at the lot to get my phone number and email and asked me out repeatedly until I very politely (he knew where I lived or I would have told him to go fuck himself with a razor) told him I was in NO way interested in a personal-information-hacking-Repo Driver.

I blocked his number and email and have been terrified of tow trucks (and their drivers) ever since. Never missed a payment again either. Worst day of my life. I’ve never told a soul. Enjoy.

4. Lynniall commented on Facebook to reveal the real reason brick-and-mortar book stores are going under.

At a large book store chain, now defunct (back in the day) wearing engagement ring and looking at wedding planning books. He walks by staring a few times smiling and trying to make eye contact, enough times to be creepy. Go to checkout and he runs up to open a new register so he can check me out (pun intended.) Starts trying to flirt and taking forever to finish the sale.

Looks at my wedding planning books and makes a random comment about having some planning to do. I say, “yes I’m getting married in a few months.” No hint taken. Asks if I want to go to lunch sometime and can he give me his number. Um, no. Really, your at work, hitting on a customer who just confirmed she’s engaged. Wow.

5. Denise wrote us an email wondering what it is about her that attracts old men. Denise: it’s them.

For some reason, older men (late 50s early 60s) like to hit on me. For reference, I just turned 30 this year and this has been going on for the past 7 years.

1) when I worked at a hotel, one of our guests (mid 50s) who was there for EMT orientation with a local ambulance company decided on his next-to-last day he would slip me his number and stated I could call him if I wanted to chat, needed a friend, or wanted to ask for “medical advice.” I didn’t call and he wouldn’t look at me the next day when it was time to check out.

2) After I left the hotel, I went to work in a hospital (so I could get real medical advice, ya’know!). We practice the three foot rule and because I worked next to the ICU, patient family members would be around the unit for days at a time. I would always smile and ask how their loved one was doing. For the record, I did this for everyone.

One gentleman’s, early 60s, common law wife had been in the ICU for a week or so, and somehow he and I ended up meeting in the hall on different occasions. As his loved one is fighting a pretty severe infection, he decided to escort me to my office and slip me his number “in case I got lonely.” My director heard the entire thing. I was mortified.

I told my friend in IT&S I don’t mind people slipping me their number, I just prefer it to be from someone who doesn’t wear their t-shirt tucked into their sweatpant shorts. Or you know, when their wife is trying not to die.

6. Here’s how I reacted while reading BooPeacock’s two-sentence story. “Wow. Whoa. WHAT.”

This super creepy guy I went to school with approached me with this weird grin on his face and proceeded to tell me how amazing I looked….In front of my husband, while I was 6 months pregnant. At my father’s funeral.

7. Jessica copped to being the flirter on FB, but really she was just “adorkable” before there was a word for that.

I was actually the one who was the “inappropriate flirter” none the less, here it goes.

I was fifteen, overweight, boy short hair, and dressed in grandpa slacks and hot topic shirts (apparently I thought this was “edgy”). I had a crush on a kid who was so far out of my league he may as well been Ryan Gosling.

I remember standing next to my locker, and noticed him looking at me.
My face must have been purple because he smirked and pointed to his cheek, as if asking for a kiss on it. I stood there flabbergasted, and he repeated the gesture, pointing to his cheek and smiling an all American boy smile. I decided that I would strut over and gracefully plant one on him, as he had so clearly asked me to do.

I remember his look of confusion as I got within his personal space, and sure enough, pecked him on the cheek. He pulled back like I threw acid on him.

Long story short, I had frosting on my face and he was pointing it out.

I called my mom bawling and made her pick me up from school. I stayed home for a week, and to this day double check in a mirror before going outside.

8. Kayla wrote to us on Facebook with two stories, both with a simple lesson: Do. Not. Interrupt. Her.

First one happened at the Gold’s Gym in Killeen, Texas. I was at the cable machine trying to get my tricep workout accomplished in peace. My headphones were in, I was in the zone. MID-FUCKING-REP, this hairy fat guy at least twice my age comes up FROM BEHIND ME and squeezed my freaking bicep, trying to be cute. I completely lost it on this asshole. From then on, he kept a wide berth.

Second incident happened at my job as a meat and produce order-filler for a grocery distribution center. I was in our meat refrigerator at the end of an enormous meat room trip that I WOULD HAVE finished at the time standard, were it not for this dude. I had to figure out how best to struggle ten super heavy cases of pork ribs on top of a 6 ft tall stack of boxes, without having the whole thing crush or tip. Note, I am tiny, so this task was annoying already.

I was struggling to OHP case #4 when this creepy douchebag from maintenance drives up and interrupts my trip to hand me his business card, then drove away like he won some big prize! I didn’t want his card or his help, but if he was going to interrupt my job, he could have at least offered to help! And thanks, dick, you cost me 7% efficiency on that trip.

Men, either offer to be productive or stay the hell out of the way!!

9. Dear dudes who watch bad rom-coms: crying women aren’t actually sad because you’re not hitting on them. From anonymous.

At a close family member’s wedding reception, a huge fight broke out between the bride’s and groom’s families. Long story short, the groom’s trashy family made a huge scene and most of the guests cleared out. I was 16 and totally upset and embarrassed.

While I was sitting outside sobbing, some guy comes up to me, tries to chat me up, and asks if I want to dance. He wasn’t even a guest at the wedding, I’m sitting there crying in a bridesmaid’s dress, and somehow he thinks this is a good move. Not so much.

10. Funerals. What can we say? They’re an aphrodisiac for idiots. Thanks, Amanda.

I was 23 and my good friend had just died in a car accident. I was at the funeral reception at her parents house talking to her mother in the kitchen.

In walks her aunt who I’m guessing at the time was in her 40’s and while my friends mom and turned to talk to someone else her proceeds to ask me to join her and her husband in a 3 some. Ummm no thanks!!

12. Jess wrote to us on Facebook to remind authorities that driving without a license doesn’t give the officer writing the ticket a license to get cute.

Got pulled over by a state trooper while I was home from college. He came back and said “Your license is suspended so you aren’t going to be able to drive home. Can you call someone to pick you up?”

I told him no and that I was by no means going to walk home, so he offered to give me a ride, since it was just a couple of miles. So as we are driving he is asking me how long I’m in town and if I’m just visiting family.

I wasn’t really in the mood to talk about these things but I figure I can at least be polite. Pull up to my moms house and this guy looks at me and asks, “so do you think while you’re here I could take you out to dinner?” REALLY dude??? How about no.

13. Dwanya on Facebook had a guy who likes safe sex and hates being appropriate.

The lab tech drawing blood for my pregnancy test with my 2nd child. My oldest was on my lap at the time. Guess he thought I’d put out…

14. Dear Cops, we love ya, thanks for protecting us, please stop hitting on teenagers in your custody. From Trieva on FB.

At around age 19 I was drinking in a car with my boyfriend, his cousin, and her (sober, driving) friend. It was around midnight and we were driving around this town of under 1000, looking for a party one of us had been invited to. We get to this 4 way stop at the same time as a police car, and we all go from laughing and talking to silent and staring straight ahead.

Of course, this looks totally suspicious, so they turn on the lights and pull us over. My boyfriend and his cousin managed to ditch their drinks, but I was holding a giant big gulp cup full of gin and lemonade and there was nothing I could do with it. While the cops were walking up to the car, we had to hide a few unopened cans of beer, one of which ended up in the waistband of my (thankfully tight) jeans.

They asked to smell my cup after I told them it was just lemonade, so I was the only one to get busted. After pouring it out, I’m put into their backseat while one writes out the ticket. As he’s writing it, he sees I’m from a different small town which is 3 hours away, and comments that he gave a ticket to a guy from that town earlier that night. Turns out the guy was in my class. Lol After that, the cop starts complimenting my hair, and flirting with me!

It worked in my favor though. He says something like “since you’re cute I’m gonna let you pick what you are getting a ticket for: transporting open liquor, or consuming in a moving vehicle ” I asked which was less, but he wouldn’t tell me. Well transporting was the right choice, because it was about $100 less for the fine. That whole time I still had the can of beer in the front of my pants.

15. Tania’s email was short on details, but we got the picture.

My grandmother’s funeral, by a family friend of my parents’ generation (He was around when I was a baby and saw me grow up)

16. OK, a funeral is bad, but this is the worst. Thanks, Mariah.

When my aunt/mother figure was dying, the doctors called me to get to the hospital asap at 3am. I rushed out in my mismatched pj’s, pink fuzzy socks, and unbrushed hair. I got there in time to be with her as she passed away, but I was a hysterical mess–you know, the ugly kind of crying.

Her doctor took me to a private conference area to say some kind words…followed by asking me out on a date so I could show him around the area as he was pretty new to town.

I just stared at him with my mouth partially open. I rarely get asked out, as I’m pretty shy, but to get asked out moments after witnessing my aunt’s death was a little much 😛


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