“If you're not comfortable enough with yourself or with your own truth when entering a relationship, then you're not ready for that relationship.”—Steve Maraboli, Life, the Truth, and Being Free
Dating can be awkward, especially when we are young and inexperienced. Thus, many—perhaps even most—of us have some serious cringy stories about our experiences in our first relationships. And by seriously cringy I mean the type of stories that make one reconsider how it is that these people are still able to function properly in the real world. The type of stories where we look back and laugh with nervous energy. The type of stories that we block out of our brain and only tell a special few close friends—or in this case, the entire internet. So, without further ado, here are some of the cringiest, corniest, and downright funniest awkward things that people have done in their first relationships. And let’s all feel better about ourselves, as we’re not alone out there in this wicked world of the game called love.
I got my first girlfriend at 18. We'd been hanging out and talking a fair bit and then we went to a friend's beach house with a bunch of other friends to spend the night and party a bit. We end up sharing a bed because she doesn't really know anyone else super well and as we're lying there I put my arm around her and she snuggles up closer.
That was already more than I was planning to do and it went pretty well so I didn't want to push my luck, but then she says, "you know, you can put your hand anywhere you want." I don't want to push my luck too much so I just put my hand on her boob over her shirt and then she says," I mean anywhere."
I think, screw it, I'm in too deep to back out now and go under her shirt. So far so good, but then I do the cringiest thing I have ever done and hopefully will ever do, I give her boob a squeeze and say "noot noot!" like Pingu... She thought it was hilarious, but a couple of my friends overheard it from the next room over and they still haven't stopped giving me crap for it about three years later.
I remember the first time we held hands. She played football on her school team, so I made some comment about how even though I have bigger hands, I still find holding the ball kind of awkward and asked her to show me how she held it.
It was an elaborate ruse to make her hold her hand up, so I could "compare hand size" and not-so-smoothly lace fingers as we put our hands back down. It was kind of cute, minus the fact that I was sweating so much that she took her hand back five seconds later to wipe my sweat onto her pants.
She was a good sport and held my hand again though.
I sat in the car with her for an hour debating whether I should kiss her. I debated out loud too, no joke. I was literally like “I could kiss you now, but should I?” Dear god, why did she ever date me?
There was this guy that I used to make out with that lived on a lagoon. We knew another person that lived nearby, so we could use her paddle boat to pass by the back of his house. We didn't see him out in the yard, so desperate and hormone-fueled young me starts yelling his name to see if he'd come out (this was pre-cellphones).
I yelled and yelled for a long time, doing circles in the paddle boat, and the friend I was with was like "Dude, give it up, he's not home." But he was home, he told us later that his whole family was sitting down to eat and heard me screaming his name over and over like a cat in heat. So embarrassing.
My ex's mom wasn't a big fan of me so I wrote a 13-page paper introducing myself and proving why she should give me a chance…
We weren't official yet so when he held my hand in public I told him we can only do it for five seconds at a time and I would literally count down, out loud, the seconds... Yeahp.
We still joke about it and I still cringe.
This was less a relationship and more a crush... He was walking me to the subway station, and I wanted to hold his hand. I reached for it and he just kind of... kept his hand stiff. So I walked with him with our palms flat against each other's, held out in front of us. Why 15-year-old me, why?
Driving back from the drive-in theatre, she takes her bra off under her shirt because it is uncomfortable and my next move? Turn on my Barenaked Ladies CD and recite all of "One Week."
I don't think I hit the high notes in the purest form as it didn't seem to have the intended effect of wooing.
I was too clingy and insecure. He would hang out with his friends and I'd text him, "Hi, do you remember me?" I was just this psycho. I would not date my younger self.
For some reason, I pretended like I didn't ever eat. I would never eat around them. It makes me cringe to think about it now.
First kiss of the relationship.
I wanted to try and do the thing from the movies where you passionately grab the other person on both sides of their face and pull them into a dramatic kiss.
I ended up smushing his face to the point where he looked like he was sucking on a lemon and got pushed into a glass door.
He was nice about it though. The second kiss was much calmer and sweeter.
I had a crush on a girl and after years of innocent flirting I didn't know how to take the next step so one day I text her "I love them big ol’ boobies of yours" and she never spoke to me again. I still cringe thinking about it. It was just so out of the blue. I was just so stuck in this innocent flirting mode and didn't know how to take the next step so one day I just decided I would take a trust fall and I fell flat and hard lol.
She asked me out over snap by saying "I want to date you." I thought she was joking (I was thrilled because I like her a lot but didn't want to jump into saying yes and have her just be kidding). So I go downstairs and my reply was me holding a bag of prunes and I say "I don't have any dates but I have prunes." I am not proud of my actions and I have no idea how we are dating as of now but yeah, that worked.
I lost my virginity to my first girlfriend in the cringiest way possible. We were in missionary position and the moment it happened I kind of fell on top of her softly and cried out, “There, I gave it to you.” It, being my virginity. I don’t know why but I was emotional about it... yeah. I cringe extremely hard whenever I think about that moment.
I was freshly sixteen at the time and thankfully, my ex-girlfriend didn’t care at all. Hopefully, she never remembers that moment—because it’s seared into my brain.
A girl that I was about to start dating mentioned she really wanted to go to New Zealand at some point in her life (to a group of people, not even just to me), so I immediately priced plane tickets and lodgings to New Zealand for a honeymoon.
Then, unbelievably, before we had actually started dating I told her I had priced our honeymoon. My defense was that if things did work out, New Zealand was so expensive I'd have to start saving then.
We still dated, but only for about two months and neither of us have been to New Zealand.
Asserted my dominance over one of my jerk teachers by grabbing my girlfriend's butt outside his room and making eye contact with him through the window while we made out.
I was pretty emotional. I thought relationships were like the movies. Every moment was supposed to be schmoozy. Made a complete idiot out of my self.
We planned, to the minute, when our first kiss would be. Not too bad, right? We were both nervous and it was both of our first relationships.
I made a website with a countdown clock.
My first girlfriend told me that she would break up with me if I didn't tell her that I would break up with her if she didn't kiss me. So she wanted me to blackmail her into kissing me by having me threaten to break up. I wasn't going to break up with her if she didn't kiss me, so I refused to say that I would. So she broke up with me.
Was walking her home anticipating kissing her for the first time at her doorstep and kept licking my lips because I didn't want to kiss her with a dry mouth. Halfway to her house she looks at me and says "stop doing that." I realized I probably looked really creepy.
We were in seventh grade and had been dating for maybe two weeks. I printed a marriage certificate and showed it to her the first time she came over to my house. She called her mom and asked to go home immediately.
Never talked when we actually saw each other but texted CONSTANTLY when we weren't in the same room.
Uhg. Me and my first boyfriend (being around 13 years old) had no idea how to kiss. Our first “makeout” consisted of us just licking each other’s tongues with our eyes wide open STARING at each other. We did this in public. I will never forget the day an upperclassman laughed at us and said, “DUDE CLOSE YOUR EYES!!”
Well, she said that she thought we would be better off just being friends so I decided that I needed to do some big grand gesture to prove my love—it always worked in the movies so what could go wrong?
I practiced singing the song for weeks on my ukulele and figured that I would wait until after her softball practice was done and surprise her. I sang "You're Beautiful" by James Blunt.
It's a damn miracle anyone talked to me after that.
I wasn't a terrible singer, but I wasn't good. It didn't help that I added intentional breaks in my voice to make the song more emotionally powerful or something dumb like that. After I was done and stood in horror as her friends laughed at me and she stormed away I kind of did a sad George Michael-esque walk in the rain to my car as I contemplated what would be easier moving school districts or just driving off a cliff.
We were not friends after that, it was super embarrassing for her and everyone teased her for months by signing James Blunt songs to her. I definitely had it worse, but high school kids are jerks. It also didn't help that about two weeks after we were assigned as lab partners and she raised her hand and asked the teacher if she could switch partners and the whole class snickered. It seems sweet reading the story, but really it was super creepy and I put her in an impossible spot.
If anything positive came from it, I never had any troubles approaching women at bars etc. because I already knew what the worst possible thing that could happen was so it was only uphill from there.
We had been texting back and forth so I knew going to his house I would lose my virginity. Dude opens the door wearing a full suit for the occasion and escorts me holding my hand into his bedroom. Jesus Christ.
And what happened after was way worse than the suit. Dude had apparently told the entire neighborhood he was getting laid, and three or four of his friends broke into the house through the terrace in the middle of the deed. I promise I’m not making this up. After the whole episode was over, he left to the friend’s party without inviting me. So, he wasn’t really a gentleman after all as the suit had suggested. A couple days later we broke up. At the time I felt horrible, but now it makes for the juiciest story.
First real girlfriend in high school, we used to talk over the voice calls on MSN messenger late at night. She wanted to just hear my voice, and I very quickly ran out of things to say, so she said I should just read whatever book I had around.
She spent the next 30 minutes listening to my "Your new Gateway Computer and how to use it!" booklet.
I was 17. We had just had a fight. I drove to his house and blasted “Scars” by Papa Roach from my car and just stood awkwardly at the end of the drive way waiting for him to come out.
I really wish this weren’t true.
Told her I loved her within the first 24 hours at the school parking lot.
Let my mom purchase custom matching airbrushed shirts of two people kissing, with my girlfriend's and my name on them.
Back in eighth grade, I could not wrap my head around the obvious signals he was giving me that he was not as into the relationship as I was. I was extremely clingy and would draw doodles of us and write the mushiest notes to him on the daily.
I would quiz him on what he liked about me on AIM every night. Fishing for compliments from him constantly. Making up a new pet name every week. My best friend was dating his best friend (who most likely felt the same reluctance due to the intensity) and we would arrange "double dates" that were mostly me and her trying to find a way to corner the boys and make-out, which was extremely creepy behavior, looking back on it.
Reading my journal from that year is horrifying. Wish I could go back and apologize for the cringe. If you're reading this, sorry about that stuff Mitchy-poo.
If a text went unanswered for more than 5-7 minutes, I would hit resend. Again and again. And this was like 2007 so phone plans were not what they are now and I was using my moms which had no texting included. Poor guy and poor parents' phone bill.
After I saw Eric propose to Donna on That '70s Show I went out and got a 25¢ ring from the local Pizza Hut and proposed. At school. In front of everyone. I was 16.
To answer the burning question, she did say yes. We didn't last. Sorry, no happy ending here, just teenagers doing impulsive things.
Started dating three months before Sophomore year ended. Once summer started I completely ghosted her. Skip to the first week of Junior year, I thought we were still together. You can imagine how she reacted when I approached her for a kiss. The shame is still real to this day.
I hit my girlfriend with my car. It was a complete accident. We are still friends and it is a story that still comes up in conversation every now and then.
I was super shy back in the day and I really really liked this guy who had weirdly flirted with me in one of our classes. He told me I looked like some random celebrity when I wore my hair down and how hot she was… so I never wore my hair up again for the entirety of school.
I replied later by slipping a note in his locker but didn’t sign it. A few days after that, I threw in a t-shirt I thought he would like. He didn’t know who it was from until weeks later when he finally wore it to school to see if anyone said something. My BFF at the time did and he realized it was me. Super creepy on my end. We ended up dating for a day before we broke up because we were stupid kids.
Now, 15 years later, we reconnected and are now married. So… totally worked as planned.
Back in the AOL chatroom days, she and I would press play simultaneously on a song from our bedrooms and type out the lyrics as we heard them. It was like singing, but different…
I broke up with this girl and had told her just days before that I had really liked her. We made out and gave each other massive hickies so I got super embarrassed and had to end it after the whole school was laughing their asses off. I told her I’m sorry I lied and that I had a problem lying and that my parents were sending me to a psychiatrist to talk about why I always lie so much. So yeah I lied about lying.
Broke up with her because my best friend told me to, we were perfectly fine together but I guess I kinda worshiped the guy and his advice. He later tried asking her out when we split, we were all 14-15.
My roommate finally got her first boyfriend just before her 40th birthday. She sent him flowers at work on her birthday. He canceled his date with her that night, and I had to stay up all night with her crying.
After the first date of going to the movies (I never put my arm around her because I was too scared), we sat in my driveway, and she didn’t say goodnight because she was waiting for me to kiss her. I did nothing, so she finally kissed me. In defense mode, I lick my lips all the way around with my tongue like Scooby Doo does with the cotton candy in the theme song intro. I even did the “reeheeheeheehee.” Kill me.
Yes this really happened, I was a freshman in high school and she was a junior, I was not ready for this. Kind of creepy on her part, looking back.
Was walking her home in our neighborhood. She says her parents aren't home. I say "Cool, you have the whole house to yourself!" and walked back home, wondering if I'd ever get a chance to touch her boobs.
To answer the big question: yes, I did. Eventually. Then we did more and were pretty bad at it. Then she faked a stalker in order to try to drive a wedge between me and my best friend, so I stopped seeing her. Up and down experiences all around, but hey, I got to do stuff with her for a while (once I caught on, haha).
I wore a floor length leather jacket to our first date because The Matrix was really cool at the time.
I was 15 at the time. My mum bought it for me from a leather shop in Glasgow (which makes the story either better or worse, your choice). There was no second date.
Early in my current relationship, neither myself nor my girlfriend wanted to be the first to say "I love you." To avoid saying it I once said "I like you with all the likes in the world."
I wrote the girl a poem. It included the phrase, "slightly too large nose" and also used the word K-mart.
It was something like this: "With your slightly too large nose and your great big heart, A love like this can't be found at K-Mart."
She started to ignore me at school (this was like maybe one or two weeks after we started dating). I called her house like six or seven times one afternoon after school until her mom picked up, who was basically furious because I had been calling. I explained to her that Alexa was ignoring my calls. I hear in the background.
"Alexa why aren't you answering the phone??" To which she responds, "Because he's weird and he just keeps calling!!"
I hung up the phone and went to my room. I carved her name in my wall with a pen. I still cringe about it to this day.
My first make-out session with someone was with my first girlfriend. We were in her bedroom, turned out the lights and went at it on the floor of her room. After a while a feel something wet on my face, I didn’t want to stop so I just ignored it and carried on.
She notices it too and decides to turn on the light because something is really wet on our faces.
Light comes on and turns out I’d had a massive nosebleed and there was blood EVERYWHERE. I was covered in it, she was covered in it and there were bloodstains all over her room.
If that wasn’t embarrassing enough when she went to the bathroom to clean up her mum caught her in the hallway. She sees the blood and immediately screams. Her assumption was that I was beating her daughter up and I got chucked out of the house.
Took a long time and explaining for me to show my face there again.
Also lost my virginity to the same girl to Kool and the Gang's "Celebration." That was mega cringey too.
It’s true what they say: money makes the world go round. In order to succeed in this life, you need to have a good grasp of key financial concepts. That’s where Moneymade comes in. Our mission is to provide you with the best financial advice and information to help you navigate this ever-changing world. Sometimes, generating wealth just requires common sense. Don’t max out your credit card if you can’t afford the interest payments. Don’t overspend on Christmas shopping. When ordering gifts on Amazon, make sure you factor in taxes and shipping costs. If you need a new car, consider a model that’s easy to repair instead of an expensive BMW or Mercedes. Sometimes you dream vacation to Hawaii or the Bahamas just isn’t in the budget, but there may be more affordable all-inclusive hotels if you know where to look.
Looking for a new home? Make sure you get a mortgage rate that works for you. That means understanding the difference between fixed and variable interest rates. Whether you’re looking to learn how to make money, save money, or invest your money, our well-researched and insightful content will set you on the path to financial success. Passionate about mortgage rates, real estate, investing, saving, or anything money-related? Looking to learn how to generate wealth? Improve your life today with Moneymade. If you have any feedback for the MoneyMade team, please reach out to [email protected]. Thanks for your help!
The Moneymade team
If you like humaverse you may also consider subscribing to these newsletters: