Rebound: I Slept With a Crazy Woman

Sometimes you choose to have sex even though it's a terrible fucking idea.
Publish date:
April 17, 2012
rebound, Dating, casual sex, anonymous single guy, M

Weekend Prince/Whiskey

It's Sunday night. It's nearly midnight. I'm alone in my apartment and feeling, well, stupid. There are times when you can see a wreck coming, but you can't avoid it. Your curiosity draws you toward the oncoming collision and your mental steering wheel locks up. Maybe that's too figurative. How's this -- sometimes you choose to have sex even though it's a terrible fucking idea.

I have not seen A (trying to maintain a professional work relationship), B (business trip), or C (sinus infection) for the last few days. Boredom and the aforementioned curiosity led me to make plans with a former coworker, D. Let's go ahead and call her Crazy D. We met up about six hours ago. She just left my apartment. I feel like I can breathe again.

I can't help but think I would've been more inclined to avoid Crazy D if things had gone better on Friday night. That was the night I had arranged for a party at a bar called Sweet and Vicious for my friend Dan and his fiance, Louisa. They recently decided to take the leap and I envy them. They possess one of the few relationships I observe regularly that seems to run smoothly.

I'd like to say I made arrangements with Sweet and Vicious and set up the Facebook invite simply because I love Dan and Louisa. I do, but I also had a secondary motivation. Louisa has a friend named Lauren, who is very beautiful.

We've met a few times and we've always gotten along really well. Lauren's one flaw is that she's been engaged for the last four years. She hasn't told me that. In fact, I wouldn't know she was in a relationship at all if Louisa hadn't told me. Alas, Lauren still plans to eventually get married to her fiance. She told me this after we had flirted and smiled knowingly at one another for most of the night.

She said that she and her fiance weren't like other couples -- that they respected each others' space and were best friends. They were just waiting for the right moment. I just nodded.

I looked at my phone during the long walk home. I had four texts from Crazy D. The first was inquiring about how I was doing since my breakup. The fourth was a mishmash of characters that was neither question, nor statement. "Crazy" is not a jab; it’s an observation.

Crazy D seems to have some sort of mental breakdown every time she drinks too much and that’s quite often.

Here's an example of one such breakdown: Two years ago, I introduced Crazy D to one of my close friends when I was first dating X. I got a call from my friend a week later as I was waiting for my baggage at JFK, having just returned from a business trip in Los Angeles. He was whispering. I told my friend to speak up, but he said he couldn’t, because Crazy D was currently in his bed. It was 8:30 pm.

My friend continued whispering that he had met up with D for happy hour drinks. After D had about four or five cocktails, my friend said she was blathering about all kinds of nonsense. She then threw herself at him.

He told me he wouldn't have called, but Crazy D’s post-coital comments were so strange he had to tell me. Apparently, while lying next to one another, she revealed to my friend that she had feelings for me. He said it was the weirdest after-sex chat he's ever had. He called me a "Fucker" as if it were my fault and then told me he had to hang up before she realized he was making a call.

D drunken text-messaged my friend for many weeks after that. Misspelled and desperate were the nature of these correspondences. He showed them to me. They came in between 11 pm and 2 am and often were requests for him to come take her away. She wanted to be rescued. Her second and third texts to me on Friday night, also misspelled and nearly inscrutable, had a similar tone.

On Saturday morning, I texted her back ...

Me: Did you get home alright last night? You texted me and sounded pretty faded.

Crazy D: Yeah. Thanks for checking up on me. I'm good. Fun times!!!

We traded a few more messages throughout the day before D asked if I wanted to have drinks. Crazy D is a former college athlete and will participate in any Zog Sports league you put in front of her, so Isuggested we watch the Knicks on Sunday afternoon at a bar near my apartment.

The superficial justification was that it would be a nice way to catch up. It was wholesome -- daytime and watching sports. Nothing would happen, I told myself.

Of course, it would be a lie to say I couldn't foresee another outcome. The situation might also allow D to drink during the game to the point of horniness, while not to the point where she reached her patented form of incoherence. We could then have a fun -- a Sunday hookup that was more of a physical activity than an emotional one. In other words, it was wishful thinking of the worst kind.

The next day I made my way to Bounce, where Crazy D and I were meeting. A few weeks earlier, I had my male friends come over for a housewarming/excuse-to-drink bourbon party at my apartment.

As a joke, one of my friends brought whiskey and a pack of Weekend Prince. He and I had joked about what we called “Bodega Boner Juice,” i.e., so-called male enhancement supplements that are sold next to the register at corner groceries. Before I left the house, I noticed the package still sitting on my counter. Why not, I thought.

The third quarter of the basketball game had not yet concluded when Crazy D asked if she could see my new apartment. She had only four or five beers in two hours. I hoped she was still in relatively good shape. D locked arms with me en route to my place as we headed down 5th Avenue. She told me X and I together never made sense and that it was wonderful that I was now free to do whatever I wanted.

As soon as we entered my front door, the dance began. The frantic, biting kisses. The removal of clothes. The scrambling hands. I turned the game on my TV to drown out any noise, because I am a good neighbor.

D and I then climbed into my bed. More groping. Things progressed to the point where she felt it was time to reveal that she had her period. Still, she wanted to "taste" me.

She may sometimes be unstable, but D brought the ideal amount of enthusiasm to oral sex and finished me magnificently with her hand. We both drifted off into a nap as the final seconds of the game ticked down.

When we awoke, it was 9 pm. I was aroused. Could it be the Weekend Prince?

Crazy D asked if I wanted her to blow me again. It felt like an odd move -- too much, too soon and slightly desperate. Who blows someone twice on the first date, I thought. It seemed surreal. Still, I did not say no.

Crazy D stuck around for another hour after she finished me for the second time. The conversation was mostly small talk just like nothing had happened. It was all pleasant enough until we were standing in the doorway saying our goodbyes. Two quick questions and I realized I had made a grave error.

Question #1: I've been wanting this for so long. How long have you knew?

Me: Um, I'm not sure. Today was great, though.

Question #2: So how many girls are you dating? I don't want to just be another piece of ass.

Me: OK ... You're not.

I told Crazy D that I am dating “a couple girls.” I told her I'm trying to be as honest as I can with everyone. My tone was a mixture of surprise, confusion and panic. She smiled and kissed me. She said she couldn't wait to see me again.

When the door closed behind Crazy D, I shook my head. I saw this coming. I must not lead on Crazy D or give her another inch. However, I'm not sure how to ignore her without feeling guilty. After all, in the last three hours, the girl did blow me twice.

Single Guy is a newly unattached 30-something living in New York City. These are his real journal entries, which he'll be sharing here on a weekly basis.