Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me at dating.itscomplicated[at]gmail.com!

 

While dating my first girlfriend, we had gone out to dinner probably at a diner or something. All I remember is that I drank a lot of soda (hey I was like 17). By the time we made it back to her house I had to piss something fierce but she had to use the bathroom too. She politely let me go first. I bolted into the bathroom and took a piss only to find out after I was finished that my pee had been shooting in two directions (WTF) and while one stream was aimed perfectly into the toilet, the other was aimed directly down my left pant leg. I had just pissed myself at my girlfriend's house. Seeing as how I was a loser in high school I wore those pants with the zip off pant-legs so you can turn them into shorts. I slyly unzipped the pant-legs and made them into shorts and then complained all night about "how warm it was inside" in the dead of winter. She never said a word about it but I think she knew.

-Anonymous

While helping my girlfriend get prepared for her summer semester abroad, I convinced her that she will need to get a new watch because Europe is on "metric time".  I said they have 100 hours instead of 24 hours in a day. She says, "Oh yeah, I forgot about that".  Good luck finding your new watch!
-Dan, ND State

So me and my (ex) girlfriend went to Texas (my old home town) to stay for about 3-4 days. And onmy step fathers land he had a single wide trailer for us to use while he stayed in his newly built house. Well one morning after waking up me and my GF decide to start at it again. In the middle of sex she asks me to moan for her. I don’t really do that, but I didn’t care so I did so and probably sounded like a girl doing it because I was faking it. So we get done and I start heading to the shower and outside in the living room (near bedroom door) is my step dad on the couch just laughing saying "well son it sounds like you had fun". Now he probably thinks I sound like a girl having sex.

-E-Brake, Army (deployed currently)

Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me at dating.itscomplicated[at]gmail.com!

 

Recently I was watching the opening ceremony for the Olympics with my girlfriend and her mom. Seeing as how we are in high school we find it hard to keep our hands off of each other. During the commercials her mom leaves the room to go make popcorn and my girlfriend instantly jumps on my face. After making out for a few seconds she pulls away in disgust. Both of our faces are covered in blood. As soon as we discover which one of us is bleeding profusely out of their nose (of course its me) her mom comes back into the room and is welcomed by the sight of her daughter's face smeared with blood. We both ran to the bathroom and cleaned ourselves up and then explained the situation. I would love to know what went through her mom's head during that first second when she saw us...

-Anonymous

 

I broke up with my girlfriend because I was not ready for a child and she was demanding one.  I then knocked-up a girl I had a one night stand with three weeks later.
-M

 

Let me begin by saying I’m 6’1”, 180lbs, and for no apparent reason, my ex-girlfriend that I dated for over 2 years was convinced that I was going to become fat.  Last year towards the end of second semester, my roommates and I were having a bonfire with some casual beers, hot dogs and s’mores.  My then girlfriend decided that she was invited and showed up.  I ate a hot dog, drank a beer, and began preparing another hot dog, when she looked me dead in the eye and asked in all honesty, “Really?..….another hot dog?”  We broke up the next day.  What a great 2 years of my life.

-Anonymous

Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me at dating.itscomplicated[at]gmail.com!

 

So there I was scrolling down the CollegeHumor front page to look for articles to read and my girlfriend walked up to me as I was scrolling pass the "Hot College Girl" article. She proceeded to yell at me because I was looking at other girls.
-Mike, OU

 

My wife and I (both recent college graduates) have a 9 month old daughter together. She's just starting to eat finger foods. We usually give her a little bit of what we have for dinner so she can try new things. One night, we were having omelets for dinner, and I was about to put some on her high chair. My wife stopped me, and explained that the doctor said we shouldn't introduce eggs yet. Aloud I wondered why is that? My wife, a cum laude graduate, responded, "It's probably because of the wheat and dairy [in the eggs]. She might have an allergy."

-Anonymous

 

For our anniversary of over a year, my boyfriend gave me a sack of donut holes.
-Amanda, Texas

My girlfriend just said, "It's scary to think that one day octopuses will become people." When I asked her how that was going to happen, she answered, in all seriousness, "Evolution."
-WS

From what I understand, when a guy has sex for the first time, it usually does not last very long. However, it seems I cannot last that long even if it is my hundredth time. So every time I have sex with a girl for the first time, and I don't last long, I tell her that I have never had sex before. I'm sorry to the roughly seven girls who think they took my virginity.
-Mark, Florida

I tagged along with my girlfriend when her family was taking her to dinner on her birthday. When we were about to leave she was surprised by the staff with a sundae with a cherry on top. She quickly asked "Who wants my cherry?" I stupidly replied yes.... with her father seated across from me...
-Jake, MSU

Almost a year ago I was fooling around with a girl. She got completely naked (with no pushing by me), but before I can get my boxers off, she tells me she doesn't want to do this, puts on her pajamas, and goes to sleep. I guess technically we slept together.
-Peter, Texas

My girlfriend sleeps on the side closest to the wall so that "the monsters" won't get her.
-Kevin A., Ryerson University, Canada

This girl and I were making out with each other for the first time. We were going along fine until she suddenly stopped and pulled away. Now I was 15 at this point and able to grow some solid facial hair, and was proudly sporting some chin stubble. Pulled away, she looks at me and says, "Your chin hairs remind me of my grandpa" and continues to make out with me.
-Anonymous

My (ex-)girlfriend broke up with me about two weeks ago. Yesterday, she got mad at me for letting her do it. I don't understand girls.
-Sean

Recently my girlfriend and I got into a conversation about sex toys. Being adventurous types, we decided we wanted to try out a vibrating cock ring. I went online and found one that looked pretty good and ordered. A day later I got a shipping notice saying that it would arrive at my apartment in three days. On the day it was scheduled to arrive, I waited expectantly at my house, but much to my disappointment, the package never arrived. The next day, I checked the order status online and it said that it was delivered. That's when I notice the company I bought it from had switched my apt number with my street address number, reversing them. That's right, a package with my name on it, containing a vibrating cock ring got shipped to one of my neighbors.
-Peter, TX