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

I lost my virginity in his grandmother's basement, with Star Wars playing in the background.
-O

I was recently dating this guy who I was really hitting it off with, and he seemed really into me. I don't usually seriously date but I wanted to be monogamous with him. He told me he wasn't looking for anything serious since he just came out of a 3 year relationship, and I understand that. One day we ended up talking about how many other people we were seeing. He said 2, and I said 4, but I don't f*ck any of them. He no longer talks to me because I am 'sleezy'…
-Anonymous

This girl that I am currently seeing came over to my house one night and decided that she wanted to stay over. I am still a virgin and she is not, she knows that I am still a virgin and I guess is totally ready when I am ready. Anyways, we start making out on my bed. I try to take her bra off secretly, didn't work, then we just kind of kept on making out some more. I pulled her on top of me and she started grinding the sh*t out of me, I was at "full attention" and after a couple of minutes I jizzed in my pants. The moments after were kind of akward, but I played it off like any smart person would, "I have to go to the bathroom". I don't know about you but getting grinded with shorts filled with jizz does not really feel the best.. Well I guess it's alot better than a zipper on the dick.
-Anonymous

I was seeing this girl one summer while I was home from school but unfortunately both of us were living with our parents so we obviously couldn't be as independent as we would have liked. One night I was at her house and we were drinking and watching a movie but after her parents went to bed we went at it multiple times. She was paranoid about throwing the condoms out at her place and wanted me to take them with me and throw them out, as she said "anywhere but here." Well, being a little drunk and a lot tired, I wrapped them in a paper towel, put the paper towel on her kitchen counter, and turned to say goodnight. Then I left. Without the paper towel. I remembered the next day after each of us was on a train to NY. I left her parents a gift of two used condoms on their kitchen counter.
-BT

My ex and I had spent the night at a frat party with his friends and ex girlfriend from out of town, when we turned in early for "alone time". Things were going along nicely when, in mid-thrust, his cell phone rings, so he stops, DOENS'T pull out, answers it, gives detailed directions to his ex on how to get to his place so she could crash on his couch, hangs up, and procedes as if nothing had happened. I decided that he could pick up where he left of with her instead and left.
-L.A., Purdue University

I had been dating a girl in high school for about a year and a half. One day we were home alone watching a movie in my basement on the projector screen. To be kinky and James Bond-intro ish (I guess??) she wanted to give me a bj with our shadows against the screen while I was standing up. I thought this posture was going to be bad news bears (since she never swallowed). Minutes later I hear footsteps a floor above, realizing it was my dad in from his errands I leaned back to re-pants myself but not before she did a snake-like tongue move, sensitively causing me to shoot a load directly into her right eye.
-Anonymous

I met a girl at a bar while drunk. We went back to her place and one thing quickly led to another. Only problem was my bad case of whiskey dick wasn't going to let me finish, and after a while I was getting very tired. So a few minutes after she climaxes I decide to fake my own. As I start my acting performance she demands I take off the condom and bust on her face. I just stopped dead, completely at a loss for what to do and very confused. She somehow takes this as an insult and gets mad, and starts calling me horrible names and insisting I leave her house. I refuse, as I have no way of getting home and demand I at least get to sleep on her couch. She runs to her friends room butt naked, wakes up her friend, and tells her to throw the "dickless loser" out of the house. The friend, curiously unfazed, smoothly assures her that I will come in her face in the morning, and that we should get some sleep. This was the start of a 2 month relationship I should of ran from when I had the chance.
-Jack

The "There's a Lot of Holes in this Story" Award goes to:

So this guy I know was really kinky. He liked to eat his gf out all the time. One night, they were experimenting, and he stuck four starbursts up her vagina. He sucked four out and ate them all. The next few days she was really uncomfortable down there. So she went to the gynecologist, who pulled out a starburst. She told the guy this but my friend was sure he ate four. So they went to the doctor to figure this out. Turns out she had herpes and he sucked out a "herpes sac". And ate it.
-Varnes, MN

^Varnes, I have a few questions for you. She was uncomfortable for a few DAYS? They went to a doctor to figure out how many he ate? He was eating out a girl with herpes sacs? He didn't realize that herpes and starbursts taste differently? That's all. See you all next week.