41 Hilarious Times A Guy Was Clueless That A Woman Was Flirting That Will Have You Laughing Out Loud

1. Google To The Rescue

One time I was texting my bf and told him that I bought a vibrator for the nights he was away at work or something rather. His exact response was, “Oh, cool, what colour?” I sent him a pic of it and he replied with “can you put it up your butt too?” I sent him a text replying, “come over and find out” and he replied two minutes later, “nevermind, I just Googled it.”


2. Yeah bro!

Put out my hand for him to hold and he high fived me.


3. Rehearsing

Me: so you’re saying, if I like this guy, I should just be straightforward and ask him out?

Him: ya

Me: ok, do you want to go out with me this Friday?

Him: ya, just like that, it was perfect.



4. “Friend’s Kiss”

My then-not-boyfriend and I were waiting at the train station on my train home; he would leave with the bus after it arrived. My train came and I thought ‘fuck it’ and kissed my then-not-boyfriend on the mouth. Immediately after, I jumped on the train, on which the doors then closed. I didn’t see his reaction nor felt it so I sat pretty anxious on the train, thinking I ruined it all. About 5 minutes later, I got a text saying:

‘That was meant as a friend’s kiss, right?’

Lol, bless his heart.


5. Cannonball!

Last summer I was doing my best to seduce who is my current boyfriend. We were going swimming at a friend’s house, and while they were changing into their bathing suits in the house, he and I make our way to the pool.

I take advantage of this moment to strip in front of him, as sensual as possible. (Bathing suit was underneath my clothes.)

He runs past me, full sprint, and cannonballs into the pool.


6. Caffeine Comes First

Halloween morning 2014, he knocked on my door to drive me to work. We had been friends for a month and he wouldn’t make a move, so I answered the door in a T-shirt and cat ears and absolutely nothing else; that bastard walked right past me and looked for coffee in the kitchen.


7. As Dense As A Black Hole

I knew this girl for a year and kinda had feelings for her the whole time. We got close for a few weeks and one time I’m watching some films at hers. It gets late and I start to head out, she says “I don’t want you to go.”

Thinking she was just feeling lonely or whatever I follow her upstairs and we get in bed… and do nothing. Lights go out, we start going to sleep. I’m sitting there the whole time thinking “damn, I wish I had the balls to make a move” but don’t.

Then she sits up, takes her top off in a way I couldn’t possibly miss, and lies down again. Still, I don’t get that SHE’S trying to make moves on ME.

10 minutes later she finally gives up and just kisses me. She mocked me about this for months after.


8. When’s Later Tho?

Hint: “Want to have sex in the shower later?”

Response: “sure!”

~later, in the shower, waiting forever, door left cracked open… I give up.~

Question: “Why didn’t you come into the shower??”

Response: “Oh! I didn’t know you wanted me to!”


This has happened more than once.


9. James Bond Strikes Again

I told him he could come home with me after the movie and show me a move we saw during a sex scene. He didn’t go home with me. I don’t think it was because he found me unattractive, but I can’t be sure anymore.

The movie was one of the latest James Bond flicks where he sneaks onto the enemy boat and manages to sex up the lady in the shower on the way. I also wouldn’t have dared say something so bold if this wasn’t our fourth date and we’d already progressed to making out during that movie. I thought it was the logical last step, but he just kissed me goodbye.


10. “Best Friends”

When me and my fiance were in high school we were “best friends,” which of course meant I was too big of a chicken to tell him how I really felt. Well, my move was to always take the seat in front of him and purposely have my thong showing while we had lectures. This went on for all the classes we had together, and we had a lot. I finally had to confess how I felt to him before he left our hometown for college after three years of this game. It turns out he was a chicken too. He said those four years were the biggest tease imaginable, it’s hilarious to talk about now.


11. Thank God For Hugo Weaving!

Sighs So I’ve actually had sex with a girl before realizing she was actually into me.

She knocks on my dorm room door wearing a miniskirt and carrying a chocolate cake (a whole chocolate cake) and says she just baked it and was wondering if I’d like to try some. I tell her that I’m not a big fan of chocolate (crushing her) but was intelligent enough to add that I’d like try it anyway. We set the cake aside. I invite her in and she asks what I’m up to.

I tell her the truth, that I was about to start watching V for Vendetta, and she squeals that she loves that movie and asks if she can watch it with me. We lay down on my unfolded futon and start watching it together under a blanket (this was in the dead of Boston winter).

We’re watching the movie and she starts making all these comments about Hugo Weaving. “I love Hugo Weaving so much.” “God, Hugo Weaving is so hot.” “Man, Hugo Weaving makes me so horny.” And all this time I’m like “yeah he’s a great actor I loved him in the Matrix.”

Maybe 20 minutes pass by and all of a sudden I feel her rubbing up against me and she’s, well, touching herself. “Sorry, I hope you don’t mind, I just got really horny and couldn’t help myself.” And here I am thinking I’m the luckiest dope in the world and I’m so glad I picked a movie that had Hugo Weaving in it. Of course, I say something like “oh, uh, that’s OK. I understand. I have actresses that really do that for me, too.” And I do absolutely nothing because I still don’t get that she’s coming onto me.

Another ten minutes of this pass before she just turns to me and asks “Can I suck your dick?”

And my mind– my very underdeveloped pathetic mind– my very first thoughts were “Hugo Weaving is such a great wingman” and “Damn talk about being in the right place at the right time.” It took me another year before I realized it was all a ruse to get to me and I could have been watching any damn movie at all the whole time with more or less the same result.


12. Thanks for the compliment!

This girl was sitting with our group of boys and saying “if I was to get with one of you, it would be you [my name]” And I was just like “Ah thanks very much, very kind of you to say that.”


13. A Closer View Of His Beautiful Eyes

Hitting on my now boyfriend of three years. I was complimenting him on how handsome he was and how he had beautiful eyes. I wanted a closer view of them so he texted me this creepy ass shot of his eyeball with his eye as widely opened as possible. He legitimately thought that’s what I wanted. After our first date, I immediately started talking about potential future dates and how much fun I had with him. I stayed out so late that I missed my friend’s party. However, because I didn’t hug him properly and asked to split the cost of the meal, he thought I wasn’t actually interested.


14. This Girl Is A Genius

When my gf and I first started talking she kept leaving hints saying if I wanted to come in for a night cap or if I was too tired to drive, I could stay the night and share the bed. But since I wake up at 4 am for work I told her I was pretty tired and I think I’m gonna go home and it’s not that far of a drive. When I arrived home, I found this link from her


15. Hmm, That’s Interesting

I was laying down on a bench with my head in his lap talking about our previous /experiences/ (this was high school) and he told me he had never had a bj before. I told him, with my head in his crotch, that I could blow his mind. Nothing. Crickets.


16. Didn’t Realize It Was A Date

Asked a guy for his number after a Meetup. Went on a date with him that he didn’t realize was a date until his friend that we ran into texted him to apologize for crashing it. Currently sitting on the couch next to him, 3 years later, looking at dogs that are available for adoption. He eventually caught on.


17. Password Sharing

I started talking to a guy who was behind on Game Of Thrones. So I offered to give him my HBO password so we could watch it at his place, thinking it would be a good excuse to hang out. He ends up marathoning the show without me. We’re dating now, but he sure as hell better not watch season 7 without me.


18. The Thoughtful Fool

A long time before my husband and I started dating we were partying in my apartment. He said he was going to crash on the couch. I told him “you can come sleep in my bed.” I shit you not he said “well where would you sleep? I can’t kick you out of your bed.”


19. Don’t All Funny Girls Do This…?

After many moons of trying to get this guy in bed I straight up humped his leg in an act of horny desperation. He thought it was hilarious. Years later he asked me why we never hooked up.


20. Killing The Mood

I have a pole in my living room. So one day I dressed like a school girl and waited for my boyfriend to get home. He walks in and I started doing some pole tricks and he literally walked past me into the bedroom to change. I was like ‘uh hellllooooo I’m trying to fuck’ and he said ‘oh I just thought you were dressed like that’.

He kinda killed it.


21. Padded Or Not?

I was at a party drinking with a guy I had a bit of a crush on. We were joking around and I told him to touch my boob because he jokingly accused me of padding my bra (since they’re quite large).

He DID touch them for a second, but then he just kept going on with the conversation. I figured he wasn’t interested and I got over it.

I think he realized his mistake cause he always made it a point to like everything I post on Facebook.


22. The Movie Lover

I was the guy.

Her: Let’s hang out after school, nobody is going to be at my house

Me: Ok cool

Drive her home and hang out with her.

Her: Hey I have a finished attic I like to hang out in and watch movies

Me: Ok cool

Go in the attic where a couch, sheets on the floor, and a TV on a stand are chilling. Turn on some random movie and she proceeds to cuddle on me.

Her: So what do you want to do?

Me: Idk random chatter about movie

Her: My last boyfriend couldn’t last more than 2 minutes with me. No guy has actually.

Me: Oh I could do better than that

Her: Oh yeah? ;)

Me: random chatter about movie

This is not a fire drill folks, this actually happened. She ghosted me pretty hard after that and I didn’t really understand why until fucking years later when I critically thought about that situation.


23. Just Being Friendly

My ex-boyfriend was pretty reserved and had limited experience with girls when I first met him. It took forever for it to click with him that I was into him. I would convince him to sleep over at my place or let me sleep at his to “snuggle.” I would wear nothing but a t-shirt and panties. I would literally press my body up against his and talk to him with our faces an inch apart. I would whisper in his ear and rest my hand on his thigh an inch away from his package.

It took over a month of this before he realized I wasn’t just being “friendly!”


24. Saving On Water

I was living with my then-boyfriend a few years ago. Feeling a little flirtatious, I suggested we could take a shower together, you know, to save water, wink wink.

His response? “Why? We don’t pay for water.”

Shut. Down.


25. Prom

When I was a Senior in High School during prom season, there was this girl in most of the classes I was attending. We were good friends, we had much in common, we were at the top of our class. Also, I thought she was cute. One day she and her friend approaches me during lunch.

Girl: Hey, don’t you wanna ask me something?

[Raises eyebrows]

Me: ………..I don’t know, what?

[She and her friend gives each other a look]

Girl: Are you going to prom?

Me: I’m not sure, I don’t have anyone to go with.

End scene.

I didn’t get the hint until years after. But I did end up going to prom with the fellas. I’m a fool.


26. A Discussion Of Clear Hints

So my former best friend and I (sadly we do not talk to each other any more thanks to an ex-girlfriend) were very close. So close even, that I fell in love with her and she apparently was with me.

So we met more often during the evening, sometimes late at night, watched movies, hung out. She got way more direct with me about being interested in me. When she was dressing up for a party and had n bra on because she was just sitting at home, she suddenly started telling me that I would not need to leave the room when she was changing clothes all of the sudden, she went all cuddly on the couch when we watched movies and I was literally thinking “I could make a move but I am very happy with the friendship I got” We even went partying and a dude started dancing with her, when she all of the sudden said something to him, pointed at me and the dude ran off (probably said something about me being her boyfriend) but I my train of thought was “She probably was not interested in that guy”

The Apex of my failure, however, was that one night, we ordered some food, hung out and we talked about the scenario, that if a person insists on someone to sleep at their place even though he/she knows the other person is not too far away from home, that is clearly a hint.

Later that evening, I was about to go home, it was late at night and I had to walk 25 minutes max. So it was not that far. She said “You know, you can sleep here, we are all alone” (since she was living with her mother who stayed at her boyfriend’s place most of the week) and I literally said, “Nah, I am good, it isn’t that far anyways.”

Those two conversations were apart like, 5-10 Minutes.

A bonus on top of my cluelessness: For her 21st birthday I gave her an iPhone. In front of all people, she went to me, hugged me, said that there is only one thing to make this moment perfect and looked me deep in the eyes. I did nothing.

Seriously. If I would have had a time machine, I would have kicked myself into reacting right now. Since it could have been the best relationship in my life.


27. WoW!

When I was 18 and foolish a girl once asked me if I was into ‘role-playing games’

I said of course! And promptly started showing her my WOW account… she left pretty soon after.


28. Keep In Mind Dudes Invented This Term

I asked him if he wanted to go to my dorm for Netflix and chill. We watched Parks and Rec for two hours and then he went home without touching me once.


29. Tipsy Is What It Takes

Texting him every day: he thought I was doing it in a friendly manner. Calling him cute names: he thought I was kidding. Asking him to judge my outfits: he didn’t think nothing of it. Making bets with him, the loser had to have something done which always revolved around sex: just joking.

I had to tell him I would have liked to have sex with him when I was tipsy, for him to realize I liked him. In the end, I’m glad I’ve had something to drink that day, or we wouldn’t have been together for 7 years.


30. Across The Country For A Cuddle

Not a lady, but I had this girl visit me and sleep with me in the same bed on four different occasions…from half across the country.

I thought we were just friends.

Ten years later I was taking a shit and it dawned on me that she didn’t travel across the country just to sleep ffs.

I feel bad for the girl now, because I was really into her too.


31. Don’t Insult A Man’s Couch

Him: “I don’t want to pressure you, but it’s pretty late and I think you should spend the night. My couch is super comfortable and I can make it up for you if you’d like.”

Me: “Maybe I could sleep in your bed with you.”

Him: “I promise the couch isn’t bad.”