16 AWFUL Dating Horror Stories (That'll Make You Feel Better About Your Love Life)

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most embarrassing dating stories

You think YOUR dating life sucks?! Look at mine and feel better.

My dating life is one that is filled with the most embarrassing dating stories, mind-bending torture, and batsh*t craziness. I will be the first to admit that part of it is my fault; I shouldn’t have chosen the guys I did as dates.

Part of it is also my fault because I did what I could to push some away. Between all the horrible mishaps I’ve had while dating, I know for a fact that at least some of these situations will make you feel better about your dating life.

For your entertainment, I decided to talk about some of the most hilarious (in retrospect) and most embarrassing dating stories in which dates have gone awry in the past and why they’ll make you feel so much better about your life on a whole.

1. One of my exes said downright idiotic things.

I swear to all that is holy, I’ve had a guy tell me that my eyes were as green as lemons. When he realized that lemons weren’t green, he changed the metaphor to roses... because roses are more romantic. I was hoping for an intellectual, here. This was not what I got.

2. I almost got arrested for listening to him.

I hate to say it, but this has happened multiple times with me. I had one idiot jump the turnstyle and get me to do it; I ended up paying a $100 fine. Another time, I had the idiot driving me home... while drunk. (I blame myself.) I should’ve dated better, more logical men.

3. I've had several people get arrested in the middle of our date.

Yes, this has happened to me, too. Seems that me getting almost arrested for dating a guy mid-crime leads to my date getting arrested. Amazing, isn’t it?

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4. His ex threatened me.

Because the only way to seriously make sure that your exes really stay away from you is to have an ex who wants you dead. This has happened to me twice, and both times, I’ve let the ex have him.

5. His mother threatened me in an “angry girlfriend” type of way.

I hate to say this, but I’ve dealt with this way too many times to count on one hand. There are a LOT of women out there who have Jocasta Syndrome and a lot of guys out there with a palpable Oedipus Syndrome.

There have been at least three or four times where my exes had moms who had angry girlfriend-type outbursts upon hearing that I was dating their son. After a while, I realized it was for the best if they continued to “have” their sons. (Yes, it felt that bad.)

6. He had a psychotic break.

Because nothing tells you that you’re meant to be better than a growling, howling man of 23 years of age. The important take away from this is that psych wards exist for a reason — primarily because they are meant to protect me from my exes. 

7. He told me he was a werewolf or an angel.

I swear to God, I had a guy who claimed that he was Inuyasha and that his kid sister was going to be the only one who could “break the spell” that was on him. Somehow, this ended with him growling while rolling on the ground, while the girl employed every single anime angel trope imaginable.

I played along until they were clearly “satisfied” with the level of lunacy they were displaying. All I could remember thinking was, “This is my life now,” and “I can never watch Inuyasha again.”

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8. He puked during a date.

I had one idiot get blackout drunk during a date and he ended up vomiting in the middle of karaoke. Of course, this sh*t happens to me. Why wouldn’t it?

9. I also puked during a date.

Happened to me twice, shortly after I got dumped by my ex-fiances. A guy who was into me proposed to me during one really bad date. People cheered, I calmly walked over to him, grabbed the engagement ring, put it on, threw up, and walked away — all while people were telling me what a great guy he was.

10. He had a poodle-squeezing moment.

I had one ex who owned a poodle. We never had sex until that night. I burst into laughter after he orgasmed 20 seconds after he got it in. He reacted by grabbing his pet poodle, making squeaking noises, and rolling around in his bed saying “I’m lame,” while grabbing his pet poodle.

The poodle made whimpering noises while he rolled in bed with it during the “lame” moments of the date, for what it’s worth. I walked away after the first 15 minutes of it.

11. Then, there was the guy who kept asking me to go to the bathroom in front of him.

Hint: I didn’t go, and he got pissed that I didn’t need to pee in front of him.

12. One of my dates came to our first date high...an hour and a half late.

Nothing wrecks your self-esteem more than having a guy who doesn’t feel like he should see you sober the first time around. Trust me on that.

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13. I also dated an aspiring rapper who was so bad in bed that I got bored and kicked him out of my room.

Yes, I hate oral sex. Yes, I told him this multiple times. He started singing during our sexual encounter (I kid you not!) and I got fed up and booted him out of my room because he kept going down on me.

Yes, I kicked him in the face, too, because he wouldn’t get away from my vagina even when I told him to stop. Also, his singing sucked and it made me happy I kicked him. My dating life sucks like that

14. His wife showed up.

Yes, this happened to me, too. No, there’s nothing I could say or do to explain how sorry I was that my date was married or that I didn’t know he was married. For the life of me, I can’t understand why so many men see me as side chick material.

15. He pooped his pants during a date. 

This happened because my date decided that nothing impresses a girl like eating brussels sprouts. He had IBS and hadn't slept in 48 hours. Somehow, this meant that I'd be amazed by him eating food he was basically allergic to.

This ended with him sh*tting himself on the corner of 34th street and 5th. I asked him if he was okay. He replied, "F*ck my life into pieces, this is my Chinese fork." Yes, drugs might have been involved. No, I couldn't see him as long-term material after seeing him sh*t himself in public.

Did I mention that he also started meowing at the Punjabi music in the taxi shortly before he sh*t himself? No? That happened too. I just want you to know that your dating life isn't that bad. 

16. I threw up on him.

Because apparently, this guy didn’t understand that feeding a girl eight rum and cokes would cause Pukefest 2008. I also vomited on his laptop, his Xbox, his clothing, his floor, and, of course, his face. Why? Because f*ck dating, that’s why.

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