10/10/2013 08:27 EDT | Updated 01/23/2014 06:58 EST

My Awkward One Night Stand With a Friend

I'd known of Jake for years. We were from the same town, belonged to the same Temple and knew the same people. But it wasn't until we wound up in the same law school that I actually met him.

We became fast friends. His very powerful and giving father had died when we were teens and I always wondered how his only son would turn out living in such a big shadow, with such big shoes to fill. Jake was not interested in being his father and was down to earth, funny, smart and kind. He was also interested in me and he was the "perfect" fit. Jewish, white, rich, educated, the whole package. There was only one problem: I wasn't attracted to him in the least.

He quickly wound up dating a demanding, spoiled, Jewish American Princess. He told me she was threatened by me, and didn't want him around me. I had never done a thing to her but due to the "rules of dating" that still perplex me, our friendship suffered. We stayed in touch and saw each other sporadically. After a few years, he broke up with her, and we became closer. Soon after, I moved and while we again stayed in touch, we obviously saw each other less.

I don't know why I decided on this, but once when I was visiting back home, I was determined to sleep with Jake. How would I know if I was really attracted to him if I didn't try?

He surprised me by going shopping, in a high end mall that I could not afford, and treated me to a lovely seafood dinner where I drank far more than necessary, mainly because I knew what was going to happen next. He took me back to his apartment and before my intoxication wore off, I made it clear he could "make a move."

See more essays from The Purple Fig

It was odd and unromantic. His place was a mess, his bed was unruly and his gentlemanly ways went out the window. He was focused on sex and sex with me. I hoped he would be a good kisser, a knowledgeable and talented lover. No such luck. We started to make out while lying on his bed and I am almost positive I tolerated it thanks to the alcohol. I quickly moved the process along and we were naked in no time. It lacked intimacy, and passion, which was expected. But it also lacked lust, ease, and pleasure. Needless to say, he came quickly and it was over. I wasn't disgusted, just unfulfilled.

The next thing I know, he is unnerved. His condom supposedly wasn't on securely, or leaked on him, I was too drunk to remember and too drunk to care. I knew he had not come inside me so I was not concerned. He asked if I was on birth control and I said no. That is when he really freaked out. He said we had to go to the drug store immediately and get the Plan B pill. He told me to dress quicker and rushed me out of the house. His state of panic, of unnecessary alarm was hilarious to me.

I tried to calm him down, reassure him, and when that didn't work, I just kept laughing, told him he was insane and that he was overreacting.

Did he honestly think I wanted his child? Did he honestly think he had gotten me pregnant? Had he never been in this situation before? He bought the pills and watched me take one. This was getting absurd. I told him I had to go home and he said he would call to remind me to take the other one. Seriously?! Sure enough, when he called, I told him I had taken it. Crisis averted.

We are still friends. We never discuss that one bizarre evening. I know he is still interested and while the idea of being with him suits many of my needs, the lack of attraction and now from experience, knowing the lack of romance, passion, talent and knowledge he would bring to the table, I don't see how I could. Perhaps if he remained a workaholic and I had mind-blowing sex with erotic and attractive men on the side, it would work. I've made my own rules thus far, who's to say that your husband can't be your best friend while someone else gives you the orgasms? Isn't that real marriage anyway? And they wonder why I'm still single.

By Janna Goldstein

The Purple Fig is a community where women share personal and relatable stories; no ego, no shame. We're about life, love and all of the stuff that makes us yearn, squirm, and giggle. These stories make up the authentic and intriguing journey of a woman.

Sign up for The Purple Fig newsletter coming out every Monday.

Visit The Purple Fig

On Facebook

On Twitter

Modern Hollywood's Casual Sex