33 People Share The Most Cringeworthy Thing A Significant Other Has Done In An Attempt To Be Romantic

Found on AskReddit.
American Pie / Amazon.com
American Pie / Amazon.com

1. The old foot trick.

When my husband and I first started dating he had never been with a lady and he was pretty clueless about what to do. We were alone one day and I was super horny so we started making out on the floor and I unbuttoned my pants hoping to get some finger action, but instead he starts rubbing me with his foot. I was like ok sure maybe he has a foot fetish and I go with it. Then he puts his big toe in me and just kind of leaves it there. I asked him about it later and he just said he was crazy nervous and had no idea what to do.

2. If you’re trying to get your boyfriend to have sex with you, don’t pretend to be a troll.

My ex crawled under my bed and attempted to get me to have sex with her while she pretended to be a troll.

3. A romantic guy if I’ve ever heard one.

He gave me a picture of “him.” It was an old pic of him and his ex cut in half. He cut it right in front of me and put the other half back in his drawer.

4. Wish someone would have told her that tampons are not sexy.

My ex-girlfriend sent me a video of her putting a tampon in. The caption was “I wish it was you.” I have no idea why she thought that would be sexy, I gagged.

5. A girlfriend who could have easily doubled as a serial killer.

After a long week of exams, I came home to take a nap before we went out for the weekend. My ex lied to my roommates to get a key to the place and proceeded to watch me sleep for 4 hours to make sure I wasn’t “disturbed.”

6. A massage from her mother-in-law.

For Valentines Day one year my ex husband got me a full body massage…with his massage therapist mother.

One hour of straight cringing.

7. A lap dance that ended in a broken nose.

My girlfriend when I was 16 tried to give me a lap dance while I was editing her English paper. She threw her head back and broke my nose. At 16 that was still kinda hot.

8. Literally whispering “sweet nothings” into her ear.

He used to think that whispering sweet nothings into my ear meant literally whispering the phrase, “sweet nothings.” Took me about a year before I couldn’t keep a straight face anymore.

9. Baby talk needs to really stop.

She tried baby talk during sex. Once. I had to stop and couldn’t finish.

10. An unexpected surprise…

One time my friend told my girlfriend at the time that I had a surprise for her the next day. In reality, I didn’t want her to know I was taking my drivers license test so that I wouldn’t have to be embarrassed in the event that I fail and have to tell her that or surprise her with my drivers license if I pass. But she thought the surprise was that I was going to propose to her. She wore a fancy dress and everything. She started crying when she heard me telling my mom on the phone that I didn’t pass. At first I was thinking “wow I was right to try to keep it a secret……damn…” But no “I…I…sniffle..thought you were gonna propose to me…”

11. A needy girl that does not know how to reciprocate.

I had a girlfriend who made it clear that birthdays were very important to her and how excited she was for the present I would get for her. I talked to her sister about what to get her and foolishly bought an $800 purse for her. She was very happy and I was looking forward to receiving my birthday present from her in a few months. She got me a Groupon for a colon cleansing. W T F.

12. A disturbing way to show one’s affection.

My boyfriend knew a girl in high school who’s ex once baked her a loaf of bread as a present. After she ate a piece, he told her that he had cut himself and bled into the dough so that a part of him would always be inside her as a symbol of their love.

13. A guy who was focused a tad too much on his unborn children.

Oh, I got one! Back in my first year of university (I was 18 or 19) I started dating a guy who turned out to be 15 years my senior (although he said he was 26). At first I wasn’t particularly attracted, but he was persistent, so we talked a fair bit on the phone before actually hooking up.

So, the first time I slept with him (at his place), one of his friends came by and he introduced me as “the mother of his future children.”

Shortly after that, the school year was over and I was going abroad for the summer. He showed up at the airport with a hand-written love note and a gift. Well, that’s nice, I thought, as I tore open the packaging, but I was confused to find a pair of baby booties and a newborn’s hat. The note inside said, “Something to remind you of our future babies.”

14. A casual romantic suicide threat.

Ex told me that if I broke up with him he’d kill himself. He did it by putting his hands on my shoulders and staring into my eyes.

I broke up with him a couple weeks later. He’s still around, but I’ve moved to a new area code.

15. Boyfriend who is bad at serenading decided to publicly serenade.

My ex during Valentine’s day decided to surprise serenade me with a guitar outside my dorm window. The thing is, I lived on the fourth floor and he decided to do it at 8AM. So, he was on the street and bellowing to me at the top of his lungs so that I could hear from my window while waking up everyone in the building. Everything would have been dandy if he were a good singer. But he’s not. There were so many people walking back and forth staring at him. He couldn’t hear me when I was yelling at him to stop. It was just an awful situation. This was the same ex who wrecked his front bumper because he dropped his car too low.

16. An anal surprise.

My one girlfriend hobbled into our bedroom excitedly. I was about to ask why she was limping when she shot onto the bed, got on all fours, ass facing me, and shot a rubber cork out of her ass. She said she was training for anal, but it just felt like a circus stunt gone wrong.

17. 15-year-old dark romance.

When I was 15 my ex wrote me a poem about how he and I should commit suicide together. He was a strange one.

18. When romance quickly turns into stitches.

When I was dating my now-wife, I was getting ready to leave her apartment for the night and decided to turn my goodnight kiss into a surprise romantic dip-and-smooch. The surprise was that I accidentally slammed her head right into an end table.

19. Poorly planned sexy time.

Had an ex who thought that it would be hot to surprise me by getting Hershey’s syrup, whipped cream, and a banana to make a sundae IN HERSELF.

Do you want yeast infections?…because that’s how you get yeast infections.

She got a yeast infection.

20. A semen-embellished gesture.

Draw a heart on the dinner table… with his semen… and surround it with candles.

21. One of the most romantic World of Warcraft dates to have ever been.

Actually, it was pretty cute and I loved it at the time because it was dorky as fuck… Still a little groan-worthy.

Back in high school my ex and I played World of Warcraft with our friends – we did an in-game “date” where he had me put him on auto-follow and asked me to keep my eyes closed. Then he took our characters to this “hidden” spot with a pretty waterfall, pond, pretty view etc. and we proceeded to have a “picnic” with our characters.

Thinking about it makes me hide my face in my hands, but we both knew it was dorky and was just a little fun. I’m just glad we went on real, regular dates too or else that would’ve been a problem.

22. A clever play on “the elephant in the room.”

Came into my house last night and found a stuffed elephant sitting on the table. While I’m contemplating why the fuck there is a Babies-R-Us elephant on a plate, my now fiancée says from the doorway “I think it’s time we address the elephant in the room” and dropped to one knee with a ring box. I’m still giggling over that one.

23. Some people just don’t know what’s sexy.

Daycare worker, told me she had a kid on her lap and came thinking about me, got the kid wet.

I ended it shortly after that.

24. And the winner of the least-caring ex goes to…

When my grandfather passed away, my ex comforted me by asking if I ever cheated on her. She was full of romance.

Edit: for those asking, I never cheated on her. Even after the break up I stayed by her side because we have a child together. I did end up moving on and finding an amazing girlfriend though, but I did stick around for a few years and was still being accused of cheating.

25. An abusive boyfriend with an inflated sense of self-worth.

While he was getting lowered into a police car for domestic violence, the last words I ever heard from him were “but I bought you Midol today!!” Apparently he thought this was a romantic gesture…

26. And the winner of the backhanded compliments goes to…

During an encounter of a sexual nature with a girl I was seeing at the time she whispers “you’ve got the 3rd biggest penis of a man I have ever been with.”

27. The ol’ tuba trick.

An older guy that I had known for a while as friends and I decided to go to out one day and after a lovely day, went back to his house to hang out & talk. He is a VERY accomplished artist and as I was looking at his artwork, I hear him call my name and I turn around and he slides out from behind a wall, all “Risky Business”-style (but on a rolling chair & thankfully with his clothes on) and starts to serenade me on his tuba. I just stood there with the most uncomfortable smile I’ve ever held in my entire life, waiting for the serenade to end. I still squirm to this day thinking about how uncomfortable it made me.

28. But how much does the thought really count?

My ex told me to come over because he wanted to fix me a romantic dinner. I went over there and he was just sitting on the couch stoned playing video games. No water boiling on the stove or anything.

…I guess it’s the thought that counts?

29. A guy who thought he could seduce by salaciously eating a Krispy Kreme donut.

My wife has the story of all stories:

She had divorced and tried the online dating scene. She met a guy on a local site that had the username of “KrispyKreme”. She had talked to him a few times and decided that he was alright. She invited him over and had her cousin standing by incase he was a creeper.

The guys username of “KrispyKreme” was obviously because that’s where he worked at the time. He at least owned it and showed up with a dozen donuts as a gift for her. After an hour she felt pretty comfortable and sent her cousin ahead so they could visit alone before she would be leaving to join her cousin at a family function.

That’s when KrispyKreme turned into “Mr. Tickles.”

The playful tickling led to the floor where he got on top of her. With his unyielding powers of seduction, he grabbed a donut from the box and began to eat it over the top of her….seductively. He tongued the middle of it and took large bites, offering his glazed covered fingers to her to lick off. She said little crumbs and pieces of frosting were falling on to her face and she was too stunned to even do anything.

When he offered her fingers to her, she turned away like a toddler refusing baby food. He simply shrugged and went on with the show.

As he wrapped up the donut and looked down at her, he did the only thing a man in his position could do.

Eat a 2nd donut.

At this point, my wife had enough and got up and kicked him out. The last thing he said to her is “Well call me later k?”

To this day, I ensure that I never eat a donut without helping her relive that magical moment again, and again, and again.

30. A beautiful card made out of…cigarette butts.

Hope I’m not too late – MY TURN TO SHINE!

My ex gave me a homemade A4 sized card ,bright pink (no less) for Valentine’s day. He decorated the card with aGINORMOUS heart made completely out of cigarette butts.

Yepp. The entire thing was a collage of different cigarette butts that he “took the time to smoke cos he lurvez me.” It was then sprayed with his cologne to make it smell more “him.”

We were 16. The relationship lasted for 6 months.

31. Latin is a romance language too…right?

My ex girlfriend got turned on by the romance languages and heavy accents. Luckily for her, I took 4 years of Latin in middle and high school. Unfortunately it’s not really a speakable language, however I memorized a few things for class assignments.

I seductively whispered the pledge of allegiance and the opening paragraph of the Caesar’s Gallic Wars in her ears more times than I can remember.

32. The ol’ diddle the earlobe trick.

During a nice little foreplay session my wife randomly diddled my ear lobe like it was a clit. She was pretty into what was going on and I guess she just did it on reflex. I pulled away, looked at her quizzically, then we both cracked up and ruined the passionate moment. Fuck it, sometimes humor is great before sex anyway.

Now ear lobe diddles are a big part of our comedic foreplay arsenal.

33. No, it’s typically not cute to try and seduce anyone with the word “chlamydia.”

A girl I used to sleep with contracted chlamydia from someone else and then claimed we both had it. She went to the doctor and get the pills or whatever, claiming she ha enough for both of us. Then her proposition: “Come over and fuck me while we are both still dirty, then we will take the meds together.” I already got tested and didn’t have it, though. Bye bye bye bitch. Thought Catalog Logo Mark

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Charlie Shaw

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