‘Women, what’s the funniest ‘he really thought this was flirting’ moment you’ve ever experienced?’ – 21 men who were way less smooth than they thought

Good flirting it s tricky thing to pull off, but usually we can tell when we’re not quite getting it right. Sometimes, however, we’re so tone deaf to a situation that when we think we’re being incredibly charming, we actually just seem a bit odd.

They’ve been chatting about this on the AskReddit page after user Doubl3oh_ posed this question:

Women of Reddit, what’s the funniest ‘he really thought this was flirting’ moment you’ve ever experienced, online or in real life?

And lots of women chipped in with some of the stranger times they’ve had at the coal face of modern dating, like these…

1.

‘I once went on a date with a guy who spent the entire time ‘negging’ me about my career. He kept saying things like, ‘It’s so cute that you think marketing is a real job’, and ‘I bet you’re the most organised person in your little office’.

He thought he was being a ‘tease’ and building tension, but I just felt like I was being interviewed by a condescending middle manager.’
–Necessary_Adagio7661

2.

‘I had a guy try to impress me at a bar by telling me in great detail about how he could ‘definitely survive a bear attack’. He spent twenty minutes explaining the physics of a bear’s swipe and how he would dodge it.

He really thought that ‘alpha male survivalist’ vibe was an aphrodisiac. I eventually just asked him if he’d ever actually seen a bear, and he said, ‘No, but I’ve watched a lot of documentaries’.’
–Sufficient_Pin_3190

3.

‘In college, a guy tried to flirt by ‘challenging my intellect’ every time I spoke. If I said I liked a movie, he’d ask me to name the director’s entire filmography to ‘prove’ I was a real fan. He thought he was being an edgy, intellectual match for me, but he just came across like a human Wikipedia page with a superiority complex. He was shocked when I didn’t want to go to coffee with him.’
–Illustrious-Sea7317

4.

‘Guy’s first words to me were ‘I like girls with big noses’. My first words to him were ‘Why on earth would you say that?”
–anonymousdlm

5.

‘During a first date the guy decided to tell me about how he’d had a threesome with two girls before. He ended that story by telling me he prefers monogamy now because it was ‘too much work’ to keep them both satisfied.’
–_purplesaturn_

6.

‘He left a note for me (his server,) about how lonely he was and that he thought I looked interesting and wanted to get to know me.

Then he stalked me at work every single day until I was actually there when he was there. Then he offered me a job (?) and asked to meet my parents because I said they’d be upset if I dated a man older than them.’
–AnalystNo1864

7.

‘I met my husbands friend and greeted him saying ‘Hi! Nice to meet you, I’ve heard a lot about you!’. And he told my husband that I was coming on to him. Like…? That’s pretty basic manners but pop off, king.’
–ozoe6046

8.

‘I had a man in a club ask me excitedly, ‘How far do you think I went in school?’ I, having just met him, said, ‘I’m not sure? Junior college?’ He laughed and slapped his hands together and said with his WHOLE chest, ‘4th grade! I never made it past 4th grade!’

Still unsure how that was supposed to impress me.’
–KillustratedPixie

9.

‘A man on hinge said ‘I know you can cook cause you have the auntie cookout arms’. I promise you I do not, I am quite fit. But even if I did what the hell kind of one liner is that?’
–Impressive-Tutor-705

10.

‘Guy once came to my house to hang out with housemates and I. I had just got home from work, and was comfortable enough around them that I threw on a jumper over my pjs – but removed my bra. Jumper was so you couldn’t see as much evidence I wasn’t wearing a bra.

But I guess he could still tell, cause he messaged me (while in the same room) to ask if this was me showing I was interested. No. I was not. I was just tired of the bra. I had to actually WORK to convince the guy I wasn’t ‘playing hard to get’.’
–CopperTodd17

11.

‘I received a “voice note” from a guy I’d met once at a party, and it was just thirty seconds of him doing a very bad impression of Batman. No context, no ‘hello’, just the Christian Bale growl saying, ‘You look like you need a hero tonight.’ He thought it was quirky and funny. I thought I was being messaged by a sleep-deprived vigilante.’
–Proper-Jeweler-1343

12.

‘Oh my god I was reading all of these thinking they were so wild, and then I remembered a story from when I was in college when a guy tried to tell me how most women didn’t know how to give a good blowjob, and then said ‘Here, I’ll show you’ – then grabbed my hand, put my fingers in his mouth and proceeded to demonstrate what a good blowjob apparently ‘felt’ like.’
–kd819