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

 

After dating my boyfriend for 3 months, we finally had sex and I stayed overnight.  The next morning when I awoke, I was covered in itchy red welts.  I thought maybe I was allergic to his laundry soap but when he flipped the mattress over, a population of insects began scurrying for cover.  He exclaimed that he knew he had bedbugs but he thought he had killed them all because he left the window open and it was "really cold" that night. :/
-Sarah

 

A friend of mine used to be a boxer and he asked me if I wanted to spar one day. It sounded fun, so I told my girlfriend I was going over there for the afternoon to box with my friend. I assumed she looked worried and upset because she thought I might get hurt. Turns out, she thought we were "starting a fight club." 
-Brandon, SLU

 

When I was 16, I was chatting online with my girlfriend. The conversation went to her family and she told me that her dad had just bought a truck. So I asked what kind and she said Chevy. Then I asked what color it is. She told me it was Silverado.

-Anonymous

In my freshman year of college, I met a girl that I hit it off with right away. We got along amazingly together and things heated up quickly. The day before I planned on asking her to make us official, she broke things off with me, as I was recovering from tonsil surgery, in order to date some other guy she met over Thanksgiving break a week beforehand. Left heartbroken, I moved on with my life and made a decision to transfer back closer to home to help out with some family issues. However, after I made this decision, her and I began talking again and things went back being great between us. Once summer came along, we started a long distance relationship and had some of the most romantic moments I could ever imagine. After a few months of dating we started talking, and since the family troubles were simmering down, she begged and pressured me to return to the school I transferred out of. I was slightly hesitant, but in the end decided to transfer back as she promised to love me forever. Following winter break, I signed my new lease and waited for her to show up four days later. With two days to go and eagerly waiting for her to show up, she called me to say she was breaking up with me and refused to give me a reason because she "didn't want to kick me when I'm down." The female gender confuses me.
-Anonymous

 

My boyfriend insists on sleeping completely naked. When we first started dating, I woke up in the middle of the night to stretch my arms and totally credit carded his asshole. It was disgusting. Two years later we're still dating, but now sleep with separate comforters. :)

-J, Western Michigan

 

My fiancé recently moved into a new house.  Because his class schedule is pretty full this semester, his parents and I decided to move some of his things and help him unpack while he was in class one day. (I realize now that unpacking my fiancé’s things with his mother while he isn't home is just asking for trouble but hindsight is 20/20.)  His mom opened a box and pulled out some mint flavored lube…and then some of my most scandalous lingerie…and then a vibrator.  She said, "Well I hope these are yours and not his."  His dad replies, "I bet they both enjoy them."  Sadly, the earth did not open up and swallow me even though I prayed for it to.

-Anonymous

 

My girlfriend moans at me for being too clingy and calling her too often, then when I don't she moans at me for acting weird and not giving her enough attention.

-Anonymous 

 

I'm an art student studying jewelry design so it's pretty much guaranteed that any girl I date is going to get some handmade jewelry. For Christmas I made my girlfriend a beautiful silver and cloisonné enameled necklace. It was one of my finest pieces and took days to complete…Unfortunately, she was more excited about the leopard print Snuggie my parents bought her as a joke.
-Anonymous

One night recently I went down on my girlfriend until she came. When I came up and was ready to have sex, she got mad at me for letting her orgasm so quickly and then angrily rolled over and went to sleep.
-Rob, Cali

 

I was watching the x-games the other night with my girlfriend when she asked me when carrot top started snowboarding… she was talking about Shaun White..

-Tyler