Dating someone? Well great! Send your craziest, funniest, most embarrassing dating related stories to me using this cool automatic submission form!

 

IT’S THE 69TH ISSUE OF THIS COLUMN! WOO-HOO!  It’s a big deal because like the number 69 is funny, you know? Cuz like it has a sexual connotation???  …I thought you’d be more excited about this…well, this is awkward…

-Jason

My high school ex-girlfriend friends every person I become friends with on Facebook.

-Mike

So I had been going out with this girl for about one and a half years and one day after class i came home to find out she was pregnant. This would be bad enough, but also we're both girls….

-Jess

I got layed because I had a hawaiian lei laying around in my room.

-Andrew K

I tried to stay with my high school girlfriend when we both went to college. We were only a couple hours apart so it wasn't too bad, but I got a little over-excited at the prospect of parties and casual sex so I decided to break up with her. We had been pretty serious and I knew she wouldn't take it well so
I planned to stop by her school on the way driving back home for winter break. That way I could do it in person and it would be right after all her finals so she wouldn't be all stressed out while she was trying to study. After a long, very tear-filled conversation she asked me why I was telling her this now. I said I wanted to talk to her during the break so it wouldn't affect her grades. I was hoping to not come off as completely inconsiderate.  Turns out I got the dates wrong. It wasn't the weekend after her finals, it was the weekend before finals.

-G B

Several years ago when I was in high school, I was enjoying getting intimate with a semi-serious girlfriend. About 2 months into our relationship, we decided to get intimate while it was "that time of the month". Being complete idiots about the situation, we decided it would be best if she left her tampon in and held the string while I did my thing. This worked for about 30 seconds, and then realized that it was failing miserably. Unfortunately, 30 seconds was long enough for her to drop the string, and it got stuck up in her. After trying for literally a half hour to get it out, we decided it would be best to wait it out but not to go to the hospital because "that would be too embarrassing" (her words not mine). Several hours later of continuous panic, stress, and frustration, we were running low on options. Just as I was beginning to persuade my girlfriend to go to the hospital, my mom came home. My girlfriend thought it was a better idea to ask my mom for assistance to get it out then to go to the hospital. Needless to say, my mom ended up pulling a tampon out of my girlfriend's vagina that got stuck up there because of my dick.

-Anon

My ex girlfriend used to blush so much that after we fooled around she would have to take a cool face clothe to her cheeks before we could go back upstairs, or else her parents would catch her red cheeked.

-Phil