Single Girl, Incredibly Amused by Men.

The dating world is an Observationist’s dream…filled with plenty of freaks, weirdos, and awkward moments.

Feel free to email me your own amusing dating stories: datingdiary2009@gmail.com

26th January 2010

Post

BILL

Bill and I have been friends for 10 years.  The summer of our 16th year of life, I was on a Teen Tour (these are very popular with jewish teens in the Northeast) with Bill’s best friend Janet.  Bill was at the Penn State Summer Program with my best friend Harry.  When we all figured this out, we couldn’t believe it.  When we started our Junior year of high school that fall, Harry and I took the train down to New Jersey to visit our new friends.  And that was the first time I met Bill.

The second time I met Bill I was at a frat party and it was my third day of college.  We saw each other from across the room, and that was that.  We spent the next four years practically attached at the hip, prone to drunkenly fooling around, and fighting openly and often, much like George Costanza’s parents on Seinfeld.  We were always falling in and out of love with each other, but never at the same time.  Finally, at the end of Senior year, Bill found himself a girlfriend.  Shortly after we graduated from college, I found myself a Frank.

I have the distinct memory of introducing Frank to Bill for the first time and Bill pulling me aside to tell me “You’re not going to marry this guy.”  I remember responding with “I might.”  And he said “You can’t.”  That was the first time Bill had ever let on that his feelings for me might be deeper than the childish passion we had ever let on to the other.

Fast forward to present-day.  Bill now lives in LA, where he is finishing up an Entertainment-MBA program.  He texted me this weekend as I was leaving a party on the LES: “Are you out?”  I responded that I was, amused that he would be asking me this from LA.  His response to me though, was to come meet him at some bar on 34th and 9th.  I didn’t believe him.  I mean, come ON, who lives in Manhattan and goes out near Penn Station?  No one.  But he was there.  I found him at some sushi/sake place near 34th and 9th and was so surprised and happy to see him!  It had been almost a year since we had last seen each other.

Towards the end of the night, he starts kissing me.  This is nothing new.  We used to fool around all the time in college.  Then he drags me into the bathroom, locks the door and starts making out with me aggressively.  Usually this is around the time when you get that feeling in the pit of your stomach, that “OHMYGOD I WANT YOU!” feeling.  But that wasn’t happening.  Part of me is afraid that I’m losing my sex drive at this point.  Regardless, we continue to make out until he asks me if he can come home with me.  I hesitated.  We had never slept together before.  I told him that I hadn’t sex in a long time, and that I wasn’t sure that my lack of judgment in that department would make a good decision for me.  He was like “Hey, it’s me.  It’ll be fine.”  And I knew he was right.  So we hopped in a cab and went back to my apartment.

Once upstairs, we opened a few beers and talked.  We talked for an hour.  We talked about how many times we had done horrible things to each other—In college, he would make out with me and then take my roommate home with him.  I slept with his best friend from high school one summer.  He slept with a few girls in my sorority house.  No matter what I did to him though, there was always a double standard.  He could do whatever he wanted, with whomever he wanted, but I always had to be the pristine virgin waiting for him to come around.  Well fuck that!  I was never that kind of girl, and I’m still not.  Especially not the virgin part.  The conversation ended with him admitting that we’ve been friends for 10 years, he always compares other women to me, and he’s so attracted to the independent, successful, beautiful woman I’ve become.

And then we had sex.

It wasn’t very good!  In fact, it was so disappointing, that I think it made me awkward afterward.  The worst part was that he clearly LOVED it.  He kept telling me how great I was.  Oy.  This was bad news.  Then we fell asleep, and I realized how much I hate having someone else in bed with me!  I wanted to sleep like a star fish all sprawled out across my bed.  And in the morning, it was worse.  I just wanted him gone.  I wanted to wake up and go about my routine and do whatever I wanted!  But I couldn’t.  Because Bill—wonderful, funny, smart, driven, best friend Bill!—was lying next to me and wanting to have sex with me again.  And so I did something that I HAVE NEVER DONE.  I told him I was not in the mood!  Who am I?!?  I’m never not in the mood!  This was bad.  But he is Bill.  And we had some laughs and he got dressed and I kissed him goodbye and managed to shout after him as he was leaving: “Call me the next time you’re in New York!”

WHO AM I?!