Managing to successfully flirt with a stranger or new love interest is a true art. It requires enough attention and empathy to pick up on the other person's interest and comfort level, but most importantly it requires the other person reciprocate. The most amusing tales of failed flirting attempts come about when one party has NO idea they're getting wooed.
In the land of men dating women, it's still more common for men to make the first move, and given the way our dating culture functions - women are pretty much veterans at getting hit on and either sashaying away or returning the wink. Because of this imbalance, a lot of straight men are still pretty oblivious or confused about when women are actually making a move, which is equal parts amusing and frustrating - depending how you slice it.
In a recent Reddit post, men shared the times they were oblivious about ladies making a move, and some ladies chimed in as well with their perspective on the situation.
1. secondstartoright said she drove the distance, and he still had no idea.
"I drove 5 1/2 hrs to hang out, no big deal hahaha."
2. rasscalkong was invited over for some sexy cake.
"A girl I worked with invited me back to her place to sample a cake she had made. We get to her place, and she explains that she just needs to frost it before we eat. Proceeds to ice the cake, periodically dipping her finger in the bowl, and getting me to taste it. After a few rounds of this, she then dips her finger in the bowl, and proceeds to porn star suck a gigantic amount of icing off it.
Me: "yeah, looks good!"
We ate cake, and I left. 19 year old me was fucking stupid."
3. ctygesen said his wife took the reigns from day one.
"My wife has had to resort to 'get up here and fuck me, already!' We met 22 years ago because she walked up to me and demanded my phone number. I'd be alone in a ditch without her."
4. Ifthenbutbe was literally shown how to open a woman's pants.
"When I was about 16 I was at a friends birthday party, she had friends from out of town visiting. One of the girls was cute and we talked for pretty much the entire night. She gave naive 16-yr old me every sign that she was into me, I thought she was just friendly. At one point we are sitting in the back of the room watching a movie with everyone and she started showing me how her Velcro fly on her pants was so easy to open, she opened and closed it in front of me multiple times. "I mean velcro is cool but it's not that different from a regular fly"
She showed me how to get into her pants and I thought she was a Velcro nerd."
5. catsandsunflowers had to wait a month for the man to catch up.
"The first date with the guy I'm dating now started with him not knowing we were on a date.
I started it by asking him "hey let's go out and explore a little bit" he said yes, and I was flirting with him while we were out said "hey let's go back to my place" he said yes, but nothing happened after that.
About a month later he made the connection that that was a date."
6. smcallaway's boyfriend was completely oblivious to a date set up.
"Not my story, but my boyfriend’s instead. Once he lost weight he was getting pretty serious flirting action. And only now is he actually noticing it. Best one is this."
"He got off work kinda late, and on his way home is a Starbucks. Normally not a coffee drinker, but he needed it (not that any of it is really coffee at that point). It’s close to closing the for the Starbucks too, around 9:40 pm. They close at 10. He orders his drink and is literally the only person in the store. The barista who took his order is about the same age and they start talking something like this."
"Him: 'Sorry I came in late, I had a long shift at work I really needed this tonight. I’ll just be up a little later and I hoped lol. I’ll probably go get some food before I go home, Taco Bell sounds good.'
Her: “Oh lol, same here.”
Pause...
Her: 'I get off of work in a little bit here myself, I think I might go get some food. Taco Bell sounds good to me too.'
Coffee is done. He grabs it.
Him: 'Well, you enjoy that food! Have a good night!'"
"Lol she was pretty much asking him to hang out after. It went right over his head. Also what was great is the last winter semester he had been talking to this girl and walking her to her car all semester. Thought about dating her...guess what happened. End of the semester comes and he never asked her for her number."
7. Optimise was literally invited to stay over and still didn't get the picture.
"I met a girl at a bar in my first week of uni. We talked for a while and went our separate ways. I met her when leaving the bar and she invited me to a house party at her house. I had planned to share a taxi with some friends so it was hard to convince me. There were about 30 people there so I agreed to go. As we got closer to her house people started dropping off in different directions. Eventually it was just her, her housemate and I. I told her it looks like this is going to be a shit party if it's just the three of us and I'd leave to meet up with my friends getting the taxi. She tried to convince me telling me that it would be easier for me to sleep in her bed with her and just walk to uni instead of commuting hungover the next morning. As I was leaving she gave me her address and phone number in case I changed my mind. As soon as my head hit the pillow in my own bed I realized what she wanted."
8. rjag36 had a woman help him move and didn't get the picture.
"I'm no lady but i look back at some spots that i was ridiculously clueless. I was a virgin up till the end of college. One of these clueless examples i am moving into a dorm and my friend is helping me. She goes all out and stays basically the whole day helping go from apartment to dorm. At the end at night we are done and im sitting on the table helping her with math and she is standing leaning over my shoulder. At some point she goes and bites my neck. Im like “ouuuuuch why did u do that?” And she is giggling and says “im gonna sleep over ok?” And im like “sure you can sleep on my bed and ill sleep on the floor” and she mumbles “thats not what i meant...” leaves shortly afterwards.
These are the moments that i would like to take back. Haha."
9. litty10 was too high to process a compliment.
"One night at a party I was very high. This girl who I had been talking to comes up next to me and says “You’re really hot”. My dumbass brain mishears her and I responded with “NO, I’M REALLY HIGH”. Took me until the next morning to register what she really said..."
10. lluren had a very gratuitous massage.
"Personal Story. i'm going to see a tinder date at her place, we talked and the subject of massages got up. I enjoy doing them, not in a sexual way, I usually do deep massage, it hurts. She asked for one, I said sure. started on the sofa, she said she wasn't comfortable enough. we went in her room. she asked of I mind about removing her bra. I said no, but still had no clue about it.
I massage without oil. She had to propose twice for me to use her oil - 3 min later she said:" you know that oil is eatable". at that point I understood it."
11. HowtfShouldIKnow was invited into a private tent and didn't pick up the hints.
"I was 16 and I was at a bonfire. A girl I really liked invited me to sleep in her tent. Literally it was just us two laying down and that’s it. She was like nudging me too and was like, “So?” And I’m like “what? Can’t sleep?” Jesus I’m dumb."
12. sexually_available spelled it out for him.
"I had the hots for this guy. Very attractive, intelligent, talented, hilarious, the works. And we were close friends. I would look at him from across the room, smile a him and make stupid faces. I would come and hug him when it was cold or I was just bored or whatever. I complimented him and listened to his stories about his childhood and him opening up about abuse and all that."
"But he had no clue I liked him. I spent weeks doing these things. And so did many other girls. But he was totally clueless and thought they were all just being friendly (he had low self esteem). So one day we were alone and I just kissed him. And it blew his mind. And then we started dating and we haven't stopped for two years."
13. Gingieloxs spent five years trying to get her point across.
"I spent almost 5 years flirting with a boy I liked in high school. Everything I could think of, compliments, gifts, spending time with him, texting him, getting to know his friends really well. I finally gave up half way through senior year because I thought he really did just think of me like a sister. Finally a friend of his was like "Jesus Christ Joe, date the damn girl." Turns out it was 5 years well spent because we got married in April and he makes me the happiest I've ever been, even if he is the most clueless person I've ever met."
14. cha_iv completely missed his date's casual sex pun.
"One time I was on a casual dinner date with a Vietnamese girl. We were talking about Vietnamese food and I mentioned bahn mis. When I did, she told me, "it's actually pronounced 'bang me'". And I took it seriously, "oh wow I never realized it was pronounced that way! Thanks for telling me!"
I didn't realize until weeks later what she was actually hinting at..."
15. pukui7 got a full cleavage view and had no clue what was going on.
"I think it was 9th grade. A girl I liked was asking me about something in class, leaning forward over my desk and giving me a full unobstructed view down her shirt. No bra. I did the gentlemanly thing and tried not to look. I didn't want to be an asshole pervert. This went on for about 5 minutes and I was sweating and couldn't really talk straight. I must have sounded like a complete idiot."
"She eventually returned to her desk and we just continued as acquaintances. My friend later told me he saw her unbutton the top of her shirt before coming over to me but I didn't believe him. I was a complete idiot. Thanks for reminding me! Lol
Edit: the point here is that sometimes the flirting can be extremely overt and we still don't get it."
16. Joe__Soap missed his chance for a sexy nightcap.
"I met a girl at bar in Germany one time and we got talking since she was also an English speaker, turned out she actually was studying at the same University as me. She seemed really chatty & added eachother on Snapchat.
After the trip when we got off the bus from the airport, she suggested that I could go back to hers for the night rather than walk home all by myself. I guess that Ryanair flight really took it out of me because despite her being surprisingly insistent on the offer I decline because I just wanted to go to bed."
"Bumped into a roommate of hers a week later who was with her in Germany, and they told me straight up she was trying to get with me. Felt pretty stupid in hindsight."
17. pantslesslizard decided she'll never use meat pickup lines again.
"There was a very nice looking man at the deli section of my grocer. I walked up, gave him some side eyes and a smile, and then said “Mmmmm, bacon.”
He turned and walked away. I haven’t tried to pick up any guys with meat related lines again."
18. pumpkinspicepiggy's husband has a confusing method of flirting.
"It was the first date with my now husband. We go out for late lunch and brews at a gastro pub. I wore a lower cut shirt, kept sitting in ways to make my boobs look good, flirty looks, took his hand across the table and rubbed his knuckles a few times, etc. He’s joking and we’re really hitting it off, but he mentions that he’s like this with all his female friends. So I feel like it’s a failed date.
I text him after the date and say that I’m not looking for anything in particular but would love to hang with him again, because I thought he was trying to let me down gently with the female friends comment."
"But I’m still into him and persistent and we end up going on a second date to the aquarium. Except he’s so busy looking at the fish (I mean, I was too, we love animals) that even though I’m linking my arm in his and making sure I lean against him looking at the fish and taking his hand to show him new stuff, he still doesn’t notice. I even get burritos with him and take him to my special spot in some nearby tide pools to watch the ocean.
And now he has the nerve to say he was flirting with me the whole time!!"
19. toomanythrowaways000's coworker consistently struck out.
"I liked my coworker from the moment I met him. And I would playfully flirt with him but he didn’t see me in any light but as a friend. Almost every time we worked together I asked if he wanted to get a bite to eat after work. Always said no. One time he was acting down so I asked if he wanted a hug to cheer him up, and he said he didn’t like hugs. I teased him cause who doesn’t like hugs? And he said “I do like them from girls I’m interested in” OUCH."
"Well like 7 months later he admitted he had feelings for me and I was like ????? And he was expecting me to tell him I just saw him as a friend, too. Had no idea I liked him. He genuinely didn’t mean anything malicious by that comment and was just socially unaware. Turns out he thought I was cute when he first saw me, and meanwhile this entire time working with him I felt like shit cause I thought he was into way cuter girls than me. Mostly cause we were like bros and would talk about the hot girls that came into work.
We talked for 3 months, dated 3 weeks.. then broke up cause he has bad anxiety. Now we aren’t even friends :("
20. cjstacy took a moment to lock eyes with a woman at trivia.
"One night, I went to trivia with some friends, as was our weekly ritual. I had in the prior year moved from across the country, and I went out to trivia wearing a baseball jersey from my hometown MLB team.
One girl on another trivia team sees my jersey and approaches me about it. She was from the same city(ish) and we talked fit a bit about moving to our current part of the country from home. Eventually she went back to her team, and I thought that was that. I don't remember many details from that interaction."
"A female friends at our table looked at me when the other girl left and was like "wtf cjstacy, she was hardcore hitting on you". I reflected for a moment and realized she was right. I played it off like "that's just part of my strategy" read: I've got no game, I'm just pretending. Her table was near the trivia host, when I would turn in our answers each round. I sent signals and got her number by then end of the night. We dated briefly, but nothing serious was meant to come from it."