Guys Reveal Their Most Awkward Moments With Girls They Liked & You'll Definitely Cringe

by Candice Jalili

If I could describe my flirting style in one word and one word only, it would be "awkward." You see, I am many things. Funny? Sure! Weird? You bet! Cute? According to some, yes! The one thing I'm most definitely not? Sexy. And no, I don't mean it in a pitiful, feel-bad-for-me sort of way. I just mean I don't have that kind of sexiness that makes people successful flirts. But it turns out I'm not the only one. One recent Reddit thread highlighted the awkward moments guys had with girls they liked, and these stories will make you feel like the Michael Jordan of getting your flirt on.

From the guy who spilled a latte on his jeans and had to wait as the milk in his latte curdled on there to the guy who made things so awkward with his work crush that she had to switch jobs, these stories may make you cringe, but they'll definitely make you feel better about some of your own awkward encounters.

His friend totally salted his game with a new girl.

Was hitting it off with a chick at a party. My buddy randomly starts asking me explicitly if I was still fucking my fuck buddy within ear shot of new girl basically ruining my shot.


Their kayaking instructor put him in a tough spot.

Met a girl on a whitewater kayaking trip. Get drunk around the campfire, end up making out. Next day we swap numbers as everyone is leaving. Start texting. The next weekend we go out on a proper date, which soon morphs into the whole weekend. The next day we're at a kayak rolling class. After the class everyone goes out to dinner. So we're sitting in the restaurant and the instructor turns to us and goes "so what are you two" cue lots of "uhhhhhhhhhhhhhh" and then theres comments from the peanut gallery "are you two an item?" (What does that even mean?) "Who has a key to who's apartment?" And all sorts of stuff like that.


He was so awkward that it made her leave her job.

I had a big crush on a coworker at an old job. We never crossed paths officially in the office so I never had an official reason to approach her. One day we were both sent to an all day offsite diversity seminar and we were the only two people from my office so we decided to befriend each other. It was great, we talked all day, had lunch, laughed, the whole nine yards.
She drove me home because I didn't have a car. When it was time to say goodbye, I decided I would just go for broke and lay one on her. Not just a peck but a full one minute tongue inspection.
Well apparently I missed some signals because we never had another meaningful conversation and she left the industry a couple of months later. Those were some awkward months


He spilled a latte on his jeans, and the milk started to curdle.

With my first girlfriend I played "the cool dude" because I used to skate and could pull it off.
We went for coffee, I spilled my large latte all over my jeans....I then insisted on walking her home because she walked through a dimly lit park in a shitty area, the milk began to curdle and was awful! She didn't say anything, but god I knew she was thinking it.


He thought they were on a date, only to find out she had a boyfriend.

I am in college and back in freshman year I liked a girl in my math class. We sat at the same table and we talked some, and every now and then talk a bit after class. I had no experience with women so I'm hopeful. One day we were having a great conversation, we walked a bit after class and came to this pond, we sat on a bench nearby and kept talking. At some point there was a lull in the conversation, and she just caresses my face, feeling some stubble from a recent shave, I thought "Oh, this is nice." Then she looked me in the eyes and said, "y'know my boyfriend could use a shave." This is how I found out that she had a boyfriend.


They met when he lunged his body into her locker.

I've mentioned this in other threads but here's the story of how I... met(?) my ex.
Get out of sign language class in high school as a freshman, cute girl is getting her stuff from her locker. Tell my friends: "wanna see something funny?" and I run straight into her locker (shoulder first) to make a loud sound/vibration and it scared her like crazy. Couldn't stop laughing at how much she screamed.
Now, as a freshman in high school, everything is funny and my goodness I must have been the most annoying turd. I repeated the process. EVERY. WEEKDAY. For well over 2 weeks. It was funny as hell to me but that is just weird/awkward in my eyes now...
We dated for 2 years


He had the most awkward comeback to her line.

I've got one. So, I was longboarding to the gym after class one day and they have these grates that help drain out the area that are right in the middle of the paths that take up a whole block of cement. You can go over them or you can jump off your board and let it roll and then jump back on once it has gone over the grate. I was feeling kind of confident that day and thought why not risk it. Mistake. The wheel got caught in one of the grates and I had to bail as I was being thrown off. Well, this cute blonde chick wearing a spirit jersey (sorority clothing) ran over to me and said "Omg, are you okay?". To which I replied "Yeah, it happens all the time" and then I chuckled a bit. She gave me a big smile and laughed. After that she offered to help me up and said "It's okay, I won't tell anyone about this". Now I attribute this to me not being in my right mind after taking a decent fall of my board and fucking up my knee and elbow pretty good, but what I said to her was and is still super fucking cringey and I don't know what the fuck I was thinking. I looked up to her and said "You better not" and then she just kind of halfheartedly smiled and walked away.


He had a classic case of a drunk text.

I made out with this really cute girl at a party one time. After the party I realised I had to see her again, howevever we never went to the same parties or anything, and dating is weird around here (Scandinavia) when you're young. Just inviting someone out over facebook is considered weird. Anyways at a party a few days later my drunken infatuation got the better of me, and at around 5am I send her a text saying something like "your cuteb <3" (with some sort of spelling error betraying my intoxication). At 9am she writes "thanks, lol" and I'm just about ready to bury myself, and spend the day attempting to do so with junk food and shame. In the evening of that day however, she writes back saying "ok, that was actually really nice of you". We have been dating for 5 months now.


All right, now, tell me you don't feel better about your own flirting skills.

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