We've all gotta go through the awkward 'first dates' at some point in our lives, and most of the time, it's better to get it over with early on. But sometimes a mixture of immaturity and lack of experience make for the most cringeworthy dating situations...
Taking The Girl To The Woods Makes For A Sketchy Situation
“On the first date with a girl, we decided to just drive around after dinner. We had a great time exploring and found this creepy road back in the woods that was closed and I decided I wanted to be a rebel and go around the barriers, but she got a little freaked out and objected.
That’s when I realized from her perspective some guy had picked her up and took her back in the woods in the middle of nowhere on the first date; Unintended creepiness but a had a second date!”
Breaking Up During The Previews Of The Movie…
“I had my first boyfriend in middle school. We didn’t last long, but when I decided it was time to break up I was at a loss as to how one goes about ending a relationship. I turned to romcoms for cues and came to the conclusion that I ought to set up a date and break up with him at the end of it.
We planned on a movie.
I arrived early and took my seat. He came in a little later, handed me some Junior Mints, and sat beside me. The previews started and I got really antsy, so I turned to him and told him I was breaking up with him.
The end result was us sitting together awkwardly and very upright for the whole movie- with me munching on the gift candy, of course.”
Don’t Kiss With A Runny Nose…
“When I met my first boyfriend I really didn’t have any experience at all; Old fashioned first kiss, first boyfriend situation.
Once we got in between the sheets one day and I assumed we needed to kiss passionately. Really passionately. I was a bit sick at the time (running nose). Lights out and I began to kiss him like a maniac. Only to notice after a couple of minutes that I was tasting snot.
I smeared snot all over his face. The poor soul didn’t say anything about it. We went to sleep. Never mentioned it. Thank goodness…”
Maybe Talk To Your Date Next Time?
“On my first date, I went to the movies with this girl and I thought it was going great. We laughed and joked about the movie and stuff. After the movie had ended is when everything went wrong.
See I had never been in this situation before so I really didn’t know what to do after the movie was over. I could have asked if she enjoyed the movie or tell her we should do something like this again but no. I decided the best course of action was to walk out the movie theater and say nothing at all.
The worst part was that she even said bye to me as I was walking out the door. This was a second chance! I could fix everything if I just turned around and said anything. Dumb old me, turned and said ‘yea see ya’ and kept on walking right out the door.
This still keeps me up at night.”
Middle School Phone Calls Are Always Awkwardly Quiet
“I called a guy in middle school. Freaked out for ages, went through an actual script (including with a friend), and finally worked up the nerve. In my head, I was going to ask him about a movie we’d talked about a few weeks earlier, ask him to see it with me, he’d say yes, and voila — happily ever after.
In reality, it went down like this:
‘H-hello? Is Brian there?’
‘Yep, this is Brian’
‘Hey, uh, it’s, um, Kristen’
‘Oh…hey, what’s up?’
‘Um nothing, you know…so uh, have you seen Fast and Furious yet?’
‘Yeah, just saw it last week with Rob’
I had no idea what to say because in my script, he hadn’t seen it. The silence was DEAFENING. He and I both stayed on the line for (not exaggerating) probably close to a minute. It doesn’t sound so long, but imagine staying on a completely silent line for an actual, entire minute.
I can’t even remember what happened after that point; if he said bye or I hung up or what. I think my middle school self blocked it out to prevent further trauma.
This is also the same guy who came up to me and asked for the time once. Unbeknownst to him, I sucked at being able to read time on analog clocks (such as the wristwatch I was wearing, which was more of a fashion accessory than anything of practical use). I got flustered, stared at my watch so long that he actually asked ‘Well?’
I shouted ‘I don’t know!’ and walked off quickly from him. Ugh…”
He Went All Out For Valentine’s Day
“I was friends with this girl and eventually asked her out and she said yes. Now I had asked her probably about two days before Valentine’s Day. The day before Valentine’s Day she told me that she had got me a gift for Valentine’s Day and that she was sure I would absolutely love it. Then she asked if I got her something and I said of course.
The thing was I had absolutely not gotten her a present. So I kind of freak out that I need to get her something. This was made worse by the fact that she was now my girlfriend so obviously, some dumb box of candy hearts would not cut it. So I begged my mom to take me to the store and I eventually got her this cool looking glass rose and a teddy bear. The total was like $80 and I spent basically every penny I had to pay for it. But I was glad that I got my girlfriend something cute and was sure she would like it.
So the next day at school I give her the gift and she was stunned. She asked me if I had bought this last night and I said no of course not I got it a couple days ago since I knew I was going to ask her out. I thought heck yeah I am awesome. I totally played this right.
Well, she looks at me embarrassed and hands me my gift. It was a bag of M&Ms. So I had to play it cool and act like this was a really cool gift. Meanwhile her friends were right there watching the whole thing unfold and totally started laughing at what happened.
It was really awkward after that and we broke up not too long after. Still one of the most awkward moments of my middle school career.”
“Never Ask For Your Date’s Food, No Matter What!”
“I was 16. I took a girl on a date. She seemed nervous as I think it may have been her first date ever.
We went to dinner for pizza. She ordered 2 slices. After she finished the 1st slice, we talked for a good 20 minutes. I thought she was done and asked her, ‘Hey so are you done with that?’ She looked at me funny and said ‘Uh yea, sure’. I happily said ‘Ok, can I eat that so it doesn’t go to waste?’ And she said ‘uhhh yea sure’. I went ahead and finished it.
10 years later we randomly ended up living in the same city hundreds of miles from our hometown and reconnected. We went out a few times (as friends, as she had a boyfriend), and one night she proceeded to lay into me how I ‘stole her 2nd pizza slice’ and I was rude and didn’t give her a chance to finish it. I thought I was fair in asking her but I learned a great lesson: never ask for your date’s food, no matter what.
And even though I thought I was fair I still cringed at the thought of her harboring ill feelings for 10 years about a pizza slice.”
Locker Notes To End The Relationship?
“My awkward 14-year-old self, went to a junior high dance stag, like the rebel that I am. I end up dancing with this boy most of the night and he asks me if I want to be his girlfriend and after I flipped my heart out and anything remaining in my chest cavity I sheepishly said yes.
After 50 hours of phone talking and a few group dates, I decide I don’t like him anymore. Either that or I was frightened of him. I was afraid to break up with him in person so I slipped a note in his locker. Probably two or so days later he calls me like normal and I’m like what the heck? I don’t think he got my note!
So instead of telling him over the phone, I slip ANOTHER note in his locker and he calls me the next day and informed me that he had, in fact, got the first note but he still wanted to be friends which is why he called.
I had to go to school with him for another 5 years.”
Toys-R-Us Isn’t The Best Place For After The Date…
“I have always been a fairly self-sufficient person. I never saw the ‘need’ to have a relationship, but at the behest of some people that worked in the shops next to mine (I was working at the mall), I asked out this incredibly nerdy, kind of handsome, giant man.
He was interesting and intelligent. We had fun while we were working at our respective stores (we would often step into the center of the path between our stores and chat and whatnot during slow times. I was surprisingly excited that he agreed to go out sometime with me. We scheduled a dinner date, followed by stargazing.
The day of the date arrives, and we meet up at Olive Garden (his suggestion, not mine!). We eat our dinner, and it seems as all is well. We finish our meal and notice it is suddenly snowing, so we decide that stargazing is out.
There’s not really much else we can do, so I start thinking of random places to go.
We end up going to Toys-R-Us and he does not look like he’s having fun. I’m checking out the random toys and looking through video games and he’s standing there looking sullen and completely turned off. I decide that we should leave, and he surprisingly gives me a kiss before he leaves.
I never heard back from him again, and our friendship never recovered. I heard from several of my friends at the mall that he was completely turned off at the idea of Toys-R-Us. I thought it was a cute idea.”
If You Lie, Don’t Post Photos Online!
“It was getting close to prom and I didn’t have a date, so I asked this girl out that I wouldn’t have asked otherwise.
3 days to prom and the girl I really wanted to ask out broke up with her boyfriend. I thought, ‘golden opportunity right here’. Obviously wasn’t. I asked her to prom, she said yes, and then I made up a story to my first date about how I forgot I would be out of town during prom weekend. She was upset but believed it.
Ended up having a really crappy time at prom, basically the worst date of my life. But it doesn’t end there. Obviously, we took pictures at prom, and stupid me decided to put them on Facebook, where girl #1 could see them. She saw them.
Long story short, neither of those girls ever want to talk to me again. Looking back I laugh at how stupid I was, but that was probably the most jerk-worthy moment of my life.”
Making Her Ex Jealous Turns Into An Awkward Confrontation
“Junior year of high school, I had a boyfriend who I really loved. He broke up with me and ended up with this other girl who he was going to take to the Spring dance. I didn’t want him to see me going to the dance alone, so I asked a friend of mine from work–who went to another school & had a girlfriend–if he would go with me.
What I wanted was just for my ex to see me with someone else, but I didn’t want to date anyone else, so I figured my friend would be safe as he had a girlfriend.
My friend, however, thought I wanted to date him and had a Very Serious Conversation with me about how he wasn’t going to cheat on his girlfriend.
When I get nervous, I start laughing…so I basically laughed in my friend’s face. I didn’t mean to. He probably thought that I was laughing at him thinking I wanted to date him, but what I was truly laughing at was the absurdity of the whole situation.”
Girls Don’t Like It When You Repeatedly Kick Their Seats
“When I was like 13-14, there was a really cute girl in my class that was very much into me during summer school. I loved the attention but didn’t really know how to handle it because I wasn’t used to that sort of thing. Other classmates/mutual friends would tease her for staring at me, and she’d reply along the lines of, ‘He’s interesting. Why do you care?’
Towards the end of the summer, she wrote down her AIM screenname on a piece of paper and gave it to me. I was ecstatic. I would wait for her to log on every day and she would wait for me. Her obsession with me made me obsessed with her.
Our class went on a field trip to the local movie theater on the last week of school, and I sat with my friends while she sat with hers directly in front of me. I had the impulse to continuously kick/push the back of her chair and I loved the way she’d react (slightly annoyed but very flirty); after like the 15th kick, however, she stopped responding and was ignoring me. I didn’t know when to stop, clearly.
In her eyes, I went from this mysterious guy with a sense of humor to a creeper stalker freak who has the social skills of a toddler.
Her AIM messages turned from infatuation to disgust. She went from obsessing over me to being annoyed at my very existence.
Now, many years later, I still cringe at my course of actions. I somehow managed to turn my biggest fan into a hater in about a 20-30 minute span. Beautiful girls make me act like an infant child.”
Why Do Guys Tell Their Parents When They Have You Over?
“When I first got with my partner he was still living with his parents so I used to go round there and we’d hang a sheet over the top bunk to hide us in the bottom.
One time we’re both naked, going at it and the door opens.
His dad strikes up an entire conversation about god only knows what while my boyfriend is poking just his head around the blanket, then his dad asks, ‘Where did you get a BlackBerry?’
‘That’s my girlfriend’s phone’
‘Oh did she leave it here?’
‘No she’s here’ … awkward silence
Apparently Legend Of Zelda Was More Important To Him Back Then
“When I was in grade 8, I went for a bike ride with a girl from my school. We went to the park, hung out and kissed too!
We get back on our bikes and head home. When we get to her house and she says ‘My parents won’t be home for a couple of hours, do you want to come in and hang out?’ to which I said ‘No, I’ve got to go home’ thinking all about how I wanted to play Legend of Zelda.
It wasn’t until I was sitting in my room, playing Zelda on my N64 did I realize the terrible mistake I’d made.”
Never Give Your SO Your Password…
“I gave my first girlfriend (we were 15) my MySpace password so she could make my page awesome, which she did. It had the Beatles’ Yellow Submarine cover as the background and all sorts of doohickeys. Anyway, we had a decent relationship, but then things ended a couple weeks later.
Keep in mind, she broke up with me.
A few months later, I decided to look at my actual page rather than just checking my profile.
Tiled across the background was a high-quality photo of a very tan and oiled dude with muscles, wearing a leopard print banana hammock.
I was angry, but she thought it was hilarious. It had been there for weeks without my knowing.
She also thought it was hilarious when she called to say she was late on her period and had had her sister take her to the doctor where she found out she was pregnant. We hadn’t even had sex, but I panicked and started thinking about how my job at Wendy’s wasn’t gonna cover all of the expenses.”
The Worst Kiss Ever?
“I’m 17, she’s 15, we met online. Thankfully I wasn’t murdered. We meet up to see a movie and being a fat guy with a mushroom cut, my mind is blown she is interested in me.
Halfway through the movie I work up the courage and put my arm around her. She leaned in. Yeah, cool guy now, I’m thinking.
A few seconds later she leans in for a kiss and I’m like ‘it’s time’, so I lean in for what I intended to be a kiss but instead blew a raspberry on her lips and turned away nervously hoping this wouldn’t be stuck as the worst first kiss ever.
The Cop Thought He Was A Creeper
“I had been dating a girl for a few months in high school, she was 15 and I was 17. On my 18th birthday I picked her up and we went to a baseball field, parked, and just talked for awhile. Nothing crazy was going to happen, we were just talking. Right behind me I see the flashing blue lights and am told to put my hands out the window. Then instructed to walk in reverse towards the officer’s voice. He asked what we were doing, I told him, he didn’t believe me. As soon as he found out I was 18 and she was 15 he decided I was a pedophile.
He made me call up her parents (we borrowed their cell phone thankfully, 15 years ago!) and her dad explained the situation to the cop. He still didn’t believe me so he made me drive her home while he followed. When I dropped her off he even waited behind my car to make sure I wasn’t taking advantage of her or something.
Her dad invited me in but I felt so sketched out that I just went home, the cop followed me the whole way.”
Don’t Bring Another Date To Homecoming When You Already Have One…
“So I was all broody and angst-ridden, and I decided that I didn’t want to go to school dances just to go, that I would only go with an actual girlfriend. So girls are asking me left and right to go to homecoming with them, (I assume just so they could go to Homecoming, I don’t think any of them actually liked me) and I keep saying no. Homecoming passes, then I get a call from a friend at a different school who complains that she’s never gotten to go to a dance and could I take her to homecoming at her school? I don’t want to go but I feel bad for her, and after some hemming and hawing, I say sure.
She lives in the country and I can’t drive outside of town, but she says that’s okay, we’ll just meet at the dance. So I go to the dance and meet her…And she’s brought another date. Seriously. No explanation. No nothing. There’s just another guy there.
I wasn’t offended. The other guy was cool. I wasn’t interested in this girl or anything. I just couldn’t figure out why I needed to be there if he was.
She apologized afterward on the phone afterward. I guess the other guy wasn’t speaking to her, so that might have been more serious. To this day, I don’t know why. Did he ask last minute and she liked him but didn’t want to cancel with me? She was with a bunch of dateless friends. Did she just want to have extra guys for them to dance with?
I’ve found her on Facebook, and I’m tempted to ask, but then, I think it’s probably kind of weird talking to women on Facebook about awkward things that happened 20 years ago.”