Women Reveal The Most Obvious Romantic Hints That Flew Over A Guys Head
Romance is a wonderful aspect of life. Whether you are still in the honeymoon stage of courtship or have been in a relationship for years, experiencing love is unlike anything else. However, not every relationship has a smooth start. In reality, relationships can be pretty tricky to navigate… especially during the period when the couple is still learning how to communicate with each other.
For many women, something as seemingly simple as getting a guy to understand their feelings and emotions can be an obstacle in itself. Sometimes, even if women voice their concerns loud and clear, some men still aren’t able to take the hint. Just take it from these women and men who recently shared the most obvious romantic hints that have flown completely over the guy’s head.
#1 Not Playing Games
I invited him over to my place to play some ‘games’ with me. I bought all his favorite snacks to surprise him and prepared what I thought to be a fun time together. I knew he was into playing video games, so I figured it would be a good way to connect. His response? I have my own console and games at home, maybe we can play online together… The guy literally couldn’t take a hint.
#2 Moustache You A Question
There was a boy in my chemistry class with a cute mustache he was growing out for Movember. We had been casually chatting for a few weeks now, and finally, I mustered up the courage to tell him that I’ve never kissed a guy with a mustache before and wondered what it felt like. He said, “You know, neither have I” and walked away. That one hurt.
#3 Killing The Mood
I completely undressed in front of him, undid my hair and told him I was going to take a bath. I even lit candles and shut the lights off. He followed me in, got my hopes up, and then just sat there fully clothed on the toilet talking to me about serial killers. For 30 minutes.
#4 No Room For Change
My husband and I were childhood friends and we reconnected when I was in college. A few weeks into dating, we were hanging out alone at his parents’ house. Then this happened:
Me: “I haven’t seen your bedroom in a while.”
Him: “It hasn’t changed.”
Eight years later, we still laugh about that one.
#5 A Miscalculation
When I was in high school, a girl from my class said I should come over and study in her bedroom with her.
I was like, “Nah, I don’t care if I fail the math test anyways.”
Also, I DID fail the math test.
#6 A Cold Encounter
A long time ago, I ran into my extremely fit, extremely attractive neighbor one night and we got into a conversation about how terrible our fridges were. After a few minutes, she asked me if I wanted to come in and check out her fridge. I was like, dang; this lady really wants to talk about her fridge; I guess I’ll be a good neighbor and listen for a while.
So, I went inside, and she proceeded to show me her fridge while standing close to me. I remember thinking wow, this lady has no concept of personal space. I honestly thought she just wanted to talk about her fridge.
I left about five minutes after entering.
#7 More Of A Tea Guy
I asked a guy out for coffee… 12 times. He would always just respond with, “I don’t like coffee much.” When I would invite him to get lunch or dinner, he’d always invite another one of our mutual friends to join in because he thought I was inviting him as a friend.
#8 Birthday Suit
My boyfriend might be the most oblivious person I’ve ever met. I’d already been flirting with him hard for months and he still wasn’t getting it. So, on his birthday, I sent a very aggressively flirty text, along with the bikini emoji that said: “Oops, looks like I lost something…” The whole conversation was dumb, but I thought it was obvious enough…
It wasn’t. Pretty sure he thought we were joking around, so instead of a steamy response, I got a, “Haha, nice one.” I got frustrated and just said, “I’m sending you nudes now, happy birthday.”
He got so flustered. It was so cute that I couldn’t be mad about my failed attempt.
#9 One-Player Game
A girl I knew found out I lived relatively close to her. She suggested that she should come over one night to play PS4 and grab a cup of tea.
I told her I only had one controller. She hasn’t talked to me as much since…
#10 Untangling The Signs
Before I started dating my husband, I went swimming at his apartment and asked to take a shower after so that I could rinse the chlorine out of my hair. I asked him to untie my bikini top because “I couldn’t reach it” and he did. I let it fall and turned around to face him topless, but he just left me alone and shut the door behind him.
He was a decent guy; I give him props for that.
#11 Thirst Trap
I went out with a girl from work to a lounge. I was 19 at the time and she was 22. She ordered a beverage and asked me if I wanted to try some. I happily accepted.
Instead of letting me sip from the cup, she took a big swig, pressed her lips against mine and let the liquid pour into my mouth. Then she did it one more time. Clearly, I wasn’t getting the hint so she left it at that.
I’m an idiot.
#12 Missing Hints Over Milkshakes
I was really into this girl in high school. After finals week was over, a few people were going to get milkshakes. As everyone was leaving, she told everyone she was just going to go home and that nobody would be there. She then turned to me, and in front of all of our friends, said, “Hey, why don’t you come by to keep me company?”
Stupidly, I said no and walked back to my house.
#13 Showered In Regret
I spent the day at the beach with a male friend. We were flirting and having a great time the whole day. We headed back to my house and we both needed to shower. I said something along the lines of, “You know, it’s hard to wash all this hair by myself sometimes,” since my hair is long as heck.
“Luckily I don’t have that problem!” he responded.
A few days later, he straight up asked me if I was inviting him in the shower with me. I said yes. He was so upset with himself, but it was cute to watch.
#14 Didn’t Catch That One
I was hanging out with a girl one Friday night and we were talking about trips we’d taken around the globe.
She mentioned that she got a pair of Pikachu undies in Japan and asked me if I wanted to see them… I told her, “Nah, that’s pretty weird,” and then left like 15 minutes later.
I still look back on that moment and get flushed with embarrassment.
#15 Benchmark In The Relationship
It was a long time ago now so I don’t remember the exact hints we were throwing at each other, but my high school sweetheart and I were super into each other for MONTHS, and we were both completely convinced that the other had no interest beyond friendship.
I’d throw out a hint and think maybe she picked up on it, but then I’d just convince myself that she was just being friendly. Apparently, she was doing the same.
This went on for more than a month or two, much to the agony of our mutual friends. Eventually, they got so sick of us fawning over each other that they lured us to a secluded bench in a park and handcuffed us both to it. They said, “We’ve had enough! She likes you, and he likes you! We’ll be back in a half hour and you better be dating by then!”
We spent the next 29 minutes making out.
#16 Missed Goal
In my junior year of high school, I was taking a girl home from the hockey banquet. We got to my car and I said, “Hey, let me know how to get back to your house from here.” She replied, “We’re not going back to my house…”
I drove her back to her house.
#17 Didn’t Work Out
I brought a girl over once and we were planning to go to the gym. I asked her if she wanted a bottle of water before we went. She said yes and I gave one to her. I turned around and she took a sip, then poured the water on herself.
I, thinking it was an accident, grabbed her a napkin and said, “Mistakes happen.” She then asked me if I can wipe off the water for her. I then said, “Why can’t you do it? We haven’t hit arms yet.”
The look on her face was literally so sad.
#18 Stripping Down To It
This one girl would constantly FaceTime me for three to five hours at a time. She would get “comfortable” and say things like, “I’m getting hot” and even change in front of me… I didn’t realize she was insinuating something until years later when she told me she had a crush on me.
Now, we’re good friends and she has a boyfriend, but I still get the feeling that she may still like me.
#19 Hot And Cold
In college, a female friend was staying with me. She went to take a shower and called for me, saying she couldn’t figure out how to make the water hot or cold. She asked me to come in and help. She sat there, butt naked and smiling. I helped make the water the right temperature and left.
#20 The Naughty List
I went to a party dressed as Santa and the moment I stepped into the room, a girl walked up to me.
The first thing she said was along the lines of, “Hey Santa, do you have a package for me?”
Me, being the awkward boy that I was, responded with, “Depends if you’ve been good.”
She then said, “Oh, I’ve been a very naughty girl.”
Then my unsocial self responded with, “Oh no… definitely none for you then,” and walked off.
#21 Message Through Massage
On our first date, we started talking about massages me up for some reason. I said something like, “Guys only give girls massages to get them in the mood.” He laughed and agreed.
On our second date, I made him dinner at my place (which should have been a hint enough, but he missed that one). We moved to the couch to watch a movie. I got tired of waiting for him to make a move, so I just said, “My neck and shoulders are killing me… How about giving me a massage?”
Well, it was the best massage I’d had in a long time.
#22 Chores Trump All
I’m a girl. My crush asked me out on Valentine’s day, but I had to run errands. So stupid.
#23 Pizza Is The Key To Her Heart
My coworkers wanted to go out after work. I lost my car to a fire a week earlier so I asked if we could head to a bar within walking distance. One girl offered to give me a ride home from whichever bar we decided to go to. We ended up at a bar that was literally a block from my house.
As the night wound down, she offered multiple times to give me a ride. I kept refusing and told her I was fully capable of walking. But she kept asking anyway, so eventually, I gave in.
As I got out of the car I said, “Welp, see you tomorrow at work,” and went inside. Five minutes later, I got a text from her saying that she was hungry. I glanced around my kitchen and saw a pizza box my roommate left out from earlier that day. So I texted back that I had some cold pizza. I finally got the hint when she showed back up in her PJs.
Exactly two years later to the day, I mentioned cold pizza in my wedding vows to her. January will be our fourth anniversary.
#24 Eskimo Kiss
I’m a guy but I have to share because I’m still so mad.
She literally put her face up to mine so I could kiss her and instead I rubbed our noses together and laughed.
I’ll forever be haunted by that.
#25 Bed-Time Stories
I had a huge crush on this guy for the longest time We worked together and every time I saw him, my heart would stop. I would bat my eyes at him say flirty things every chance I got.
We eventually became closer friends and about a year later we are hanging out in his basement getting tipsy and watching a movie with his roommate. I ended up getting a little too tipsy and started puking in his bathroom. I really didn’t want to have to drive home in this condition. Luckily, my crush offered me to stay the night at his place. He still had no idea I was into him; we had never held hands, kissed or even done anything remotely romantic but I thought success! We could crash in his bed and he could just platonically cuddle me to sleep.
I had been in the bathroom cleaning up and when I came downstairs to his room, he was laying on the couch. His bed was empty and he said I could sleep there. While this was a very polite offer, it was not what I had imagined was going to happen so I blurted out, “You could sleep in your bed too. I don’t mind, I like sleeping next to people, it helps me sleep.” I silently prayed that my tactic would work. Luckily, it did, and he crawled into bed next to me and read me bedtime stories until I fell asleep.
We didn’t cuddle and he didn’t even realize I came onto him that night until I told him a few days later. A year and a half later, it must have worked a little since we fall asleep together every night now.
#26 Nama’stay Here
After having no success with my “usual tactics” of awkwardly smiling, I attempted a more straightforward approach. I was at a bar with one of our school organizations and was eventually persuaded to go saddle up next to a guy. Instead of noticing my low cut dress, he continued his bickering with some other guys.
Somehow, hot yoga got brought up, and I blurted out “I’d love to watch you do hot yoga!” He had no idea what to do with me and the night ended with him going home despite me begging him to stay out with me. I ended up sending him a Facebook message with my phone number saying, “You don’t have my number and I think you need it.”
Six years later, we’re now married, but he still doesn’t know what to do with me.
#27 Sobering Kiss
I had kissed my now-boyfriend while extremely tipsy for the first time. I ended up forgetting my charger at his place and I texted him a day or two later asking him to drop it off at my place. He brought it over and I invited him inside to chat for a little while. I wanted him to kiss me again so badly, but he just was not catching on.
I kept getting closer and closer to him on the couch. I strung my legs over him and we even got into a tickle fight. Our faces were probably four inches away from each other for God’s sakes. He left after a while and just told me to have a good night.
I texted him later on that night saying he should come over. It was pretty clear after that.
#28 Brace Yourself
I used to have braces and this one girl who I was into looked me in the eyes and said, “I’ve never kissed a guy with braces before.” I didn’t get the message and just responded with, “Me neither.”
#29 A Lesson For The Long Haul
When I was in college, I took a film class. I sat in the back row and a girl sat next to me two seats over. During the first class, the teacher took attendance. I was first and she was second because we had the same last name. The teacher was like, “Oh, are you guys related?” I said, “Yeah, but obviously she doesn’t like me much.”
Later on, we went out for a break and when we came back in she sat next to me. During the course of the semester, she would lotion up my hands, give me massages and rest her head on my shoulder during movies. The teacher even said we were lovebirds. No one had ever made my heart flutter so much, but I’m a shy person and never made a move. I still think about her to this day.
#30 Streaming Rejection
I asked a guy to come over to watch Netflix one night. He said that he only had an Amazon Video account.
I’m not sure if the hint flew over his head, or if that was just rejection flying over my head. Either way, no Netflix or Amazon happened and I think I ended up just sitting at home with the cats.
#31 Not Cashing In
In high school, a girl was way into me. One day, she asked me to come over and take her coins to Coinstar for her so she could give her brother money for his birthday. She came out of the shower in just her underwear, showed me her prom dress and said, “Now I just need someone to ask me to prom.” I gave her the cash from my pocket for the coins and started to walk out. Took me a solid year to realize.
#32 Picture Perfect
We had been friends for a couple of years, he was studying cinematography, and he had an assignment: nudes. And I did it. I posed like a painting, naked, for him. Four months later, he finally kissed me.
#33 Not The Smartest Bird
I sent my now-husband an Awkward Penguin meme that said something along the lines of: “Realizes a girl is flirting with you… two days later.”
He responded with “That’d be me if a girl was flirting with me.”
Anyway, seven years later, he figured it out.
#34 Coated In Signs
A guy friend once lent me his coat, which he wore every day. I sent him a picture of myself in just his coat, with it unzipped a little so that it was relatively revealing. All he said about the picture was, “Oh wow, how strange.”
We are getting married soon, but damn was he dense.
#35 Just Need Some Guidance
With my current boyfriend, I asked him where the library at our college was and he told me the directions. I told him I got lost easy and asked if he could help me find it. We met at the coffee place next to the college and I held his hand. I also tickled him so he would hug me and we even shared a drink. It took him a week to realize I was into him. Five years later, we still haven’t found the library.
#36 Not The Killstreak!
My wife started to slowly pull my shorts down as I’m playing video games. I tell her that she’s going to ruin my kill streak. I got punched in my privates that day.
#37 Different Tastes
When I first met my girlfriend, we were tipsy at a party together. She came over and asked if I wanted some of the strawberries she was eating. I don’t really like strawberries, so I naturally said, “No thanks.”
Thankfully, I caught the next sign of her pulling my face in for a kiss and we have been together since.
#38 Fighting For Love
Before we started dating, I honestly thought he was gay… BUT, long story short, I would massage his back and he would massage mine. Sometimes, we’d even get into wrestling matches… But it all flew right over him.
#39 Quite The Trip
I talked to a guy for over a year. We hung out and had a sleepover, during which we planned a week-long San Francisco trip together. He then asked, “What day should I tell my girlfriend that we’re going?” Apparently, the dude had no idea I liked him and was dating other girls the whole time.
#40 Toying With Him
My wife made a small plushie toy and gave it to me for my birthday, back in the university before we even started dating. I had no clue that it might have meant something more than just a birthday gift.
#41 An Awkward Tour
I went on a date with my now-husband. Afterward, I offered him a tour of my apartment that conveniently ended in my bedroom. I even sat on the bed. He got awkward, gave me a kiss and went home…
10 years later and I still tease him about that moment.
#42 Foot In Mouth
I was in a shoe store, casually chatting with the female clerk. As I was checking out, she said, “So, can I get your phone number?” Idiot me thought she was asking for promotional stuff. I responded, kind of arrogantly, “Why?”
She just looked at me dumbfounded and replied, “Uh, so I can call you later…”
She didn’t call me later.
#43 An Icy Response
On my first date with my now-wife, we walked around my childhood suburban neighborhood. I was 22 at the time, home from college for Christmas break.
At some point, we sat on the porch and she said, “My legs are so cold!”
I replied, “Yeah, same.”
Then, she said, “Feel my thighs, feel how cold they are!” while placing my hands on her upper thighs.
I replied, “Yeah, wow, they’re cold.”
I mostly got the hint at that point but still didn’t make any move. I gave her a single peck on the cheek before she went home though.
#44 Hooking It Up
A cute guy came into the bar that I worked at and I didn’t charge him for at least half of his beverages. He would see his tab at the end of the night and be like, “Oh wow, only 40 bucks! Crazy, I’ve been here all night!”
We have been together for almost seven years now and have a two-month-old daughter. It took many more aggressive hints to get to this point.
#45 Giving Him Space
I was the clueless one. My boyfriend literally went on and on about how if we watched movies at my place we’d have to cuddle since he had no couch and only a tiny bed. I was super into him and just kept saying stuff like, “Yeah, that’s okay, I can sit on the floor or something to make space.” Eventually, he realized that I was a complete brick and took it upon himself to make moves on me, instead of waiting for me too.
Ok. At 17 I met this girl and she said come over. Let’s hang out. It’s 2 am. We hang out near her house. And at 3 am, she’s like, “Let’s go upstairs and have some coffee.”
I said “no. I’m good. I’m tired. This was fun. Let’s do it again ok?” And just left. She never responded to me again.
#47 Lost The Battle
After having met my now-girlfriend, I discovered she hadn’t seen Game of Thrones. That night, she texted me asking, “Do you want to watch Game of Thrones together?” I responded with a link to the first episode and asked, “Let me know when you start.”
I later found out she was asking me to come over to “watch the episode” with her.
#48 Dry Cleaning Is Expensive
Early interaction with my boyfriend-
Me: “That suit looks great on you. It would look better on the floor.”
Him: “That would wrinkle the suit.”
#49 At Least He Got An ‘A’
I look back on it now and see how I totally missed the hint. In college, a girl in my class came over to study and when it got late she ended up wanting to stay. I had a couch in my room and said she could sleep on the couch. When I was getting ready for bed…
Her: “I usually have a hard time falling asleep. Do you want to lay down together and watch Netflix with me?”
Me: “Nah, I got a test tomorrow”
But hey, I got an A on that stinking test.
Christina if you’re out there, I’m not gay, I’m just oblivious to hints.
#50 Do You Need A Written Invitation?
He asked if I had a boyfriend and said he was nervous to try to start something with me. I explicitly said no I don’t and you shouldn’t be. Yet he does nothing. Eventually 4 months later we end up going out, and we’re still happily together now!
#51 Bless His Heart
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 ‘screw 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’d ruined it all. About 5 minutes later, I got a text saying:
“That was meant as a friends kiss, right?”
Lol, bless his heart.
#52 Last One In’s A Rotten Egg
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 (my bathing suit was underneath my clothes).
He runs past me, full sprint, and cannonballs into the pool.
#53 Up High!
I put out my hand for him to hold and he high fived me.
#54 Signal Fail
Geesh… in middle school my best friend and I watched Scrubs all the time. We’d do a Todd high five in the hallways whenever we’d see each other, and one time the girl I had a crush on put up her hand like she wanted a five, so I smacked her hand as hard as I could and snapped… turns out she was waving to her friend behind me.
#55 Um, Hello?
Me: So you’re saying, if I like this guy, I should just be straightforward and ask him out?
Me: Ok, do you want to go out with me this Friday?
Him: Ya, just like that, it was perfect.
#56 Such A Gentleman
I love to share this one: 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 kid you not he said, “Well where would you sleep? I can’t kick you out of your bed.”
#57 Crawling Out Of Friendzone
Back when my boyfriend and I were “just friends”, there was a night I spent at his apartment after hanging out together all day. I was going to sleep on the couch, but I managed to talk my way into his bedroom.
To get myself into his room, I think I said his roommates or his neighbors were too loud. He got back up to get me a pillow and a blanket so I could sleep on his floor. I had taken off my bra and had asked to borrow his sweater at this point. After a while, I joked that he was hogging all the blankets up in his bed. He finally invited me up.
So then I said I couldn’t sleep, and suggested we stay up together to watch a movie… Netflix and chill.
I had just read that Jurrasic Park was a good date movie, so I suggested we watch it on his phone (without mentioning the date movie part. I was beyond nervous at this point.
So we’re in his bed, he’s holding the phone above our eyes, and I decide to lean on his shoulder and slowly begin the process of inching closer to him. We laid there all night, curled up yet barely touching, neither of us breaking the spell for so much as a peck on the cheek. We fell asleep.
He wouldn’t end up asking me out until more than 5 months later. We re-enacted this scene on a hotel bed after sneaking up a bottle of wine from his office Christmas party. This time, I decided to stop being so shy. After a few sips of white wine, I finally felt brave. I looked up into his eyes and kissed him.
We’ve been together ever since, and we’re moving in together in a few weeks.
#58 Must Have Coffee
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 jerk walked right past me and looked for coffee in the kitchen.
We’ve been married 10 months now!
He claims he totally knew my intentions but knew being a gentleman would get him farther, I say he’s full of it.
#59 Just Can’t Take A Hint
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]! I was just like “Ah thanks very much, very kind of you to say that”.
If only I knew.
#60 He Won’t Be A Third Wheel
Back in college, my now significant other of 4 years would walk me home from class at night. I finally mustered up the courage to ask him to “come upstairs and have some wine with me”. Hard no. Ok, he’s not into it.
Two months later, he invites me and my friends to a party. He’s blackout drunk when we show up, and tells my friend that he’s in love with me and got wasted because he was nervous about seeing me. She convinces him to tell me, knowing that I was also into him.
Curveball: Told me that he was really into me, but didn’t want to mess up my relationship. Uhrm.. what relationship? Ya know, that guy from our class that you always talk to and giggle with. Uh… Matt? As in Matt with the boyfriend, Matt? …Oh, well that strangely explains a lot.
#61 Just Be Super Obvious
This actually happened to me:
Her: Guys are terrible at picking up on hints.
Me: Tell me about it, we’re useless at it. What you need to do is be super obvious, like grab his hand and drag him into you.
Her: Like this? (She grabs my hand and starts dragging me away).
Me: Ha! Exactly like that, that’ll definitely work. Bye!
It only clicked to me two days later but I was in already in the cold-shoulder zone by then.
#62 Creepy Eyeball Shot
I was hitting on my now boyfriend of three years. I was complimenting him on how handsome he was and how he had beautiful eyes. I told him wanted a closer view of them so he texted me this really creepy 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 best 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.
#63 It’s Not About Saving Money
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.”
#64 That Must Have Been Some Movie
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: I don’t know? 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 years later when I critically thought about that situation.
#65 It Took Years?
When I was in senior in high school during prom season, there was this girl in most of the classes I was attending. We were good friends, had a lot in common, and were both the top of our classes. I also happened to think that she was very cute. One day she and her friend approach me during lunch.
Girl: Hey, don’t you wanna ask me something?
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.
I didn’t get the hint until years after. But I did end up going to prom with the fellas. I’m a fool.
#66 Baseball Vs. Baths
We were married for two full years before I finally understood that if she took a bath at night, I was going to get some.
I watched a lot of baseball while she lay sparkling clean in bed alone.
#67 That’s A Dumb Rule
I was staying the night at a female friend’s house. I had a huge crush on her and it was the first night sleeping in the same bed.
Her: Just so you know, jeans aren’t allowed in my bed. You have to take them off.
Me: Hahaha that’s a dumb rule. *Keeps them on*
That one still stings.
#68 That’s Nice
I was sleeping over at a friend’s after a party when the pretty girl I had been talking to all night suggested we sleep on the pull out couch together so neither of us had to take the floor.
We lay down:
Her: “You have great lips.”
Me: “That’s really nice, thanks.” *Rolls over and goes to bed.*
#69 The 64 Version Is Better
We were playing Super Smash Bros on Nintendo Wii together.
Her: Maybe we can play some real smash later..! *winks*
Me: You mean like the Nintendo 64 version?
Not my proudest moment.
#70 No Nintendo, Nothing Else To Do
A girl I was interested in (we’re now married for almost 20 years) took me to the pharmacy to fill a prescription of birth control pills, then says to me that she’s house-sitting for one of her parent’s friends and we could go there tonight if I wanted. I said, “And do what?” To which she replied, “Anything that you want.” To which I replied, “Do they have a Nintendo?”.
They didn’t have a Nintendo, so I didn’t go over and hang out.
She still brings it up to this day.
#71 Sweet Set Up Man
Not a lady, but a girl once asked me ”so where are you sleeping tonight?”, and I was just like “at home, I live 5 minutes away so that pretty sweet”. And it was pretty sweet until the day after when my friend told me that I’m stupid.
#72 Don’t Like Texting
Guy here. A girl I like (whose number I don’t have) recently asked if I like texting. I replied, “not really”.
#73 What’s The Secret?
Once a guy complimented me on my perfume and said something like, “you smell nice, is it Victoria’s Secret?” And I said, “It’s not from Victoria’s Secret, but I have something from Victoria’s Secret I can show you instead,” he said, “what?” Like not a sexy “what?” Like a genuinely confused one.
#74 The Tattoo
I was flirting with this boy I had just met at work. We were texting and I told him I had just gotten a new tattoo. He asked me where, and I said, “you’ll need to come to find it sometime later this week.” His response: “why can’t you just tell me where it is?”
I once flashed a guy in high school and he said: “those look weird.”
#76 Teach A Man How To Cuddle
My current boyfriend and I started out in this weird friends that flirt stage. I was trying to find a way to get him to make a move. One very hot evening (middle of August) we were sitting in his backyard with a few of our friends drinking beer. I sat on the SAME lawn chair at him, kind of wiggled in, and said, “I’m cold”.
He left me alone in the chair and proceeded to build a giant fire. It took like an hour. When he was finished making the fire he sat back down in a DIFFERENT lawn chair.
#77 Take A Hint
My husband went to a party at a friends house. The hostess asked if he wanted to see her lingerie collection, then said he should come sit on her bed with him. He said no thanks and chilled with his buddy before coming home and telling me all about it. He didn’t believe me when I said that she wanted him. This lady has tried to sabotage our relationship and failed miserably because he can’t take a hint. I found this hilarious.
#78 What A Knob
Me: I think you’re really cute and I like you. A lot.
Him:… uh, thanks.
Accepting this unrequited crush, I decided I was happy being friends with him.
However, 3 months down the line he spent hours comforting me after a disastrous night and then finally confessed he had feelings for me, going back 6 months. When I asked why he didn’t say anything when I told him my feelings “but I wasn’t sure you liked me”
That was 4 years ago, he’s still as cute and dense now, and is fast asleep next to me.
#79 Snuggle Please?
Before our third date, she said I could stay over at her place if it got late. So we’re watching a movie on TV there, and at the end of it, I said “I guess I better let you head off to bed. I’ll take the couch.”
She literally had to say “I was hoping we could snuggle” before I got the hint.
#80 Beach Bums
We were leaving the beach, and I decided to try the change the suit under the towel trick. Keeping eye contact, I told him if I messed up and flashed him, I hope he likes what he sees. He promptly turned around to give me privacy.
“I”m going regret this garlic if we kiss later.”
We didn’t kiss later.
#82 The Wrong Way
There was a time when a girl came all the way to my house from the subway. She said she didn’t live close to me but wanted my company. When we got to my place, I said bye and waited for her to call an Uber home. Later that day, it hit me that I had screwed up. I was never able to properly talk to her again.
#83 What A Ride
I was at the county fair when I was 16 and I ran into this girl that I had a huge crush on. We used to ride the bus together every day before she moved. Apparently, she was visiting that weekend and was at the fair with some friends. We ended up on the Ferris wheel together and she was holding my arm.
When we got to the top, she said, “Wow, I’ve always wanted to kiss someone on top of the Ferris wheel!” She then looked directly at me. I looked her dead in the eyes and said “Yeah, me too!” then got off the Ferris wheel, said goodbye, and went home.
I think about this moment a lot.
#84 Nighty Night
We were laying in bed together, making out, and I took off my shirt. And my bra. And my pants. “I’m taking these off. They’re so uncomfortable!”
He said, “Oh, okay. Well, good night!” and rolled over and went to sleep.
I changed my underwear in front of him and he still had no idea what to do.
#86 Take A Break
Before my husband and I started dating, we worked at the same grocery store. One day I worked up the nerve to ask him if he wanted to take lunch with me. He said, “Yeah, no.” I walked away feeling rejected. He later realized I was asking him to take a lunch break with me, and not asking him if it was time for him to take his break.
#87 One For The Ladies
As a guy, here’s a hint to the ladies: if it’s a hint, it’s too subtle.
#88 Send Nudes
#89 One For The Ladies
Me: “Want to see a movie with me?”
Him: “Sure! Who else is going?”
Worst part: Several months later, after we finally got together, he told me that he wished I had asked him to that movie as a date.
#90 Still No Idea
This was a hint that a girl dropped on me, I think. We were hanging out by the ocean, sitting on a park bench, when she put her leg on top of mine, hiked up her dress to show me her thigh tattoo. Then she put my hand on her leg. I didn’t react at all. I think I just short-circuited. But afterward, while I was walking her back, she kept asking me where my place was because I live close to there.
I still don’t know…was she hitting on me?
#91 Young and Naive
When I was a kid I had a crush on my friend Frankie who I knew also had a crush on me but we were both 12 and shy. I found a form-fitting shirt that said “Frankie’s firecracker” on the back and would wear it to hang out with him all the time, he never noticed the shirt.
#92 Get A Scoop
I kept trying to get this guy I knew to come over for some ice cream. I bought two pints and we had been talking and snapping and he LOVES ice cream. I would try and get him to take one since I only bought two because of a BOGO offer. I brought it up a few times, whenever he was in my area, I would tell him to come over and pick up some ice cream.
He never got it. Ugh.
#93 Get A Scoop
In high school, I was popular but never dated anyone. I always thought no one really liked me that much so I’d talk to all the girls in my class and would be generally nice to them. The last week of school I had so many girls ask me why I never asked them out. I was really confused and would respond with, “I didn’t realize you were interested.”
#94 Regret x 100
The first guy I was ever into, we go to his place and I lay my head in his lap. 30 minutes go by, no move yet. So, I take it upon myself to say “I’d like it if you kissed me now.” He looked surprised but in a good way, or so I thought.
He laughs and said good joke.
I fixed this hot girl’s computer in the dorm. She said, “wow it would be handy to have you around I should get your number” to which I replied, “yeah, it probably would.” I was annoyed because I didn’t want to do more tech support for people. It only took me half a day to realize that she was asking for more than just tech support.
#96 Can She Be More Obvious
I put my hand on his crotch through his pants and he still wasn’t sure if I was into him.
#97 Netflix And Bail
We were texting.
Me: Ugh I’m so tired I just want to Netflix and chill
Him: Aww… what are you going to watch?
Me: I don’t know, you should come over and help me choose
Him: I think Netflix recommends movies based on your past choices
Texted him “we should make out” and he didn’t respond.
I told him I was home alone for the weekend because my parents had gone away and that I was scared. I told him to come and hang out with me to keep me distracted.
His reply was, “lol that sounds boring.”