Rebound: The Erotic Adventures of a Newly Single Guy

Single Guy is a newly unattached 30-something living in New York City. These are his real journal entries.

Apr 3, 2012 at 1:00pm | Leave a comment

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ENTRY #1: IS SHE REALLY GOING OUT WITH SHREK?


Up until last month, I was in six straight years of monogamous relationship. The majority of that time was spent living with my partner, one woman for four-and-a-half years and the last woman for a year-and-a-half, including a short period of time being engaged to the former.

Now, for the first time in recent memory, I am single again.

My new apartment is empty and relatively unfurnished, but I've busied myself with shopping for essentials, setting up utilities and separating shared accounts with my ex, who we'll refer to as X. These mundane activities, along with exercise, my job in the media industry, and drinking with friends have been the best ways to avoid thinking about X.

X and I decided it would be best for me to move out on a rainy Monday night after months of the same argument. The honeymoon period was over and there wasn't much between us left to fight for. Over the following days, we went about our normal routines despite the fact that I was leaving work in the afternoons to look at potential apartments.

Meanwhile, the arguments had stopped. The routine was like usual. We'd come home from work. She would cook dinner. I would clean up. We would watch the shows we DVR'd and settle in together on the couch. We even had sex one evening. It was awkward though -- like we had just met that day.

We didn't much discuss my move and she never told me, "Don't go." One night, we planned to talk about it, but she didn't come home from a work event until midnight. She was drunk and apologized. I shrugged it off.

By Friday, I put an application in on a loft near my office. On Sunday, she returned late and drunk from another work event. She passed out. Her cell phone buzzed with activity. I picked it up at 11:30 and read a text from a guy we'll call Shrek (this is the nickname one of X's friends would later use to refer to him). It said "Goodnite beauty."

When she woke up at 3 am to go to the bathroom, a stream of paranoid inquiries, one after another, welled up and spewed out of me. She eventually admitted that she worked with Shrek and she had a "crush on him." That felt very sudden. I was confused.

Every day I don't talk to X, I'm feeling better. That was interrupted earlier this week when she called about the lease on the apartment we had shared, where she is still living. She was offering to let me out of the lease and return my security deposit. She wanted me to send a letter to the landlord immediately, letting him know I had left. I needled her as to why this needed to be done so quickly.

Eventually, she admitted that she was considering having Shrek added to the lease. The conversation left me feeling ill.

Fortunately, after I got off the phone, I met up with my friend Ian to attend a burlesque show at a polished club near Washington Square Park called Le Poisson Rouge. It was there that Ian would provide me with vital information I vaguely already knew, but needed to have hammered into my brain as a driving plan of action.

As we settled in and awaited the ladies, I leaned in and told Ian about the way my relationship with X ended. He seemed to study the words I uttered as if he'd heard them before, nodding every once in a while to indicate he knew what I would say next.

Ian lived in London working as a commercial director until he moved to New York with his wife about 15 years ago. The wife and his retreating hairline is the only indication of his true age. When he's not working, he often spends days smoking weed and playing "Modern Warfare." When I finished my tale of woe, he immediately launched into a pep talk he claimed to have given to nearly all his friends. Now, it was my turn.

He started by telling me that prior to his wife, he was a serial monogamist. He would have two- or three-year relationships, one after another. The conclusion of those relationships was rarely initiated by Ian. He was an accommodator and due to that, he was often the dumpee. That or he would simply discover infidelity and have to move on.

It was always crushing at first, but he developed a method for dealing with the pain quickly and effectively. Ian told me it was called "Dr. Frosty's 3-Point Plan." "Frosty" being the nickname Ian was given by his chums in London, because of his passion for a cold pint.

Dr. Frosty looked me dead in the eyes and laid out the prescription:

1. You must stay out later than you normally would.
2. You must drink and consume more substances than you normally would.
3. You must have sex as much as you possibly can, sometimes with women you wouldn't normally want to have sex with.

The Doctor claimed that if I followed these guidelines, it would take me 3-4 weeks to get over my breakup.

The dancers began coming out on stage. They were real women with curves -- teasing and jutting out their hips, stripping down to pasties and thongs. Ian's words rang true. I was already following the first two steps fairly closely. The third step is the one I need to work on.

ENTRY #2: GOT TO GET THEM INTO MY LIFE

I walked to the office last Tuesday morning expecting my day to be a fairly routine. By 10 am, I found myself in the midst of a conversation over instant messenger with a female co-worker who was inquiring about my emotional state. We'll call her A.

A is witty, slender, dark-haired, and pretty. She has always been fairly open with me about her personal life, which always seems to involve a rotation of unreliable guys. Since she's been candid, I felt comfortable telling her about my split with X and that I had set up a date that Friday with a woman we'll refer to as B. I even mentioned Dr. Frosty's three-point plan.

This led to A and I to debate whether step three was actually practical and if it might only complicate matters. At some point in the conversation, I decided to stop being coy and made my move. I asked A if she had ever considered having sex with me.

A didn't pause when I asked. She freely admitted she had lusted after me since she was an intern. I replied that I had always been attracted to her as well. Before long, we were discussing hypotheticals. By afternoon, we were planning for real and talking about how if we slept together, we had to keep it a secret from everyone.

That night A came over around 9 pm. She had a nervous energy that she channeled into declarative statements. She told me that I was not ready to date. She told me that I need to be on my own. She told me that I was still reeling from my breakup. I nodded. Then I kissed her. She tasted like red wine.

Before long, we were in my bed and I was peeling off her clothes. A stopped me when I tried to go down on her. She said it's too intimate. She was wet already anyway. I awkwardly put on a condom for the first time in over a half-dozen years and slid inside her.

The condom took away most of the sensation, except warmth. I worried about keeping my erection. Meanwhile, A made short, squeaking noises that made me think I was hurting her. I stopped for a moment and asked if she was OK. She dug her nails into my ass cheek and demanded I keep fucking her.

Around 2 am, A asked what I wanted from her. I said, "This."

She seemed agitated, then disappointed, then hurt. I reminded A that she had instructed me to not date. She told me she just didn't want to feel disposable. I told her I knew what that felt like, and nothing would make me more disappointed in myself than treating another person that way. I'm not sure A and I will have sex again, but I think we'll remain friends.

A left my apartment before I woke up the next morning. When I got into the office, I opened an email from X. She wanted to meet to give me my security deposit. It should have bothered me. It was the official end -- the last of the breakup logistics. Instead, I just felt relieved. I was glad to have my money back.

That was Wednesday. Today is Sunday. In the intervening three days, I had one date and one hookup.

Friday night was the date with B, a director at her company at the age of 28. She is the type of smart and confident that can scare off some men, but I found her company over dinner to be fun and engaging. She made me think, and I like that. She's also cute, which doesn't hurt.

She doesn't drink, so I wasn't sure what to do with her after dinner. She suggested we walk and talk. It seemed like a novel idea. When we arrived at her apartment building, we gave each other perhaps the most asexual goodnight kiss I've ever been involved in. I've kissed some of my male friends in jest with more passion.

After that, we still agreed to meet for a second date at a restaurant we both wanted to try. The politeness of Friday evening gave way to a raucous Saturday. A friend in the East Village threw a party, and his girlfriend was keen to have me meet her friend who we'll call C.

C is a soft-spoken, buxom blond, who had recently returned to the States after a rough breakup with a Spanish boyfriend she met while studying abroad. C and I became quick friends after being introduced and I was soon mixing her custom cocktails.

As the night wore on, we got increasingly drunk and I playfully mentioned how much easier it would be for her to stay with me, rather than returning home on the Metro North. She agreed as long as we both promised each other we would not be be "naughty."

As it turned out, we did not have sex. You could say it was because we kept our promise, but I suspect the real reason is most likely because I did not have non-latex condoms. During moments of acute desire while we groped and kissed at one another, she reminded me her vagina is allergic and we would have to wait until we were properly equipped.

Before she left to meet friends for brunch the next morning, we made plans for a date the following week. She mentioned she might be open to staying over again. She also urged me to purchase non-latex condoms.

Today, around dusk, I was walking home from a bar where I had met up with friends to watch the Knicks game. On the corner of 18th street and 5th Avenue, I was approached by a perfectly average, well-groomed middle-aged Englishman, carrying a shopping bag. We had the following dialogue...

Englishman: Do you know where I can find the bar Splash?

Me: Sure. It's on this street on the south side right up ahead.

Englishman: Do you know if it's fun?

Me: I've never been, but it always seems to have a line.

Englishman: Where do you usually go?

Me: Um, lots of places.

 Englishman: Where are you going now?

Me: Home

Englishman: Would you like me to come with you?

I paused for a beat. The question confused me. Why would he want to come to apartment, I thought. Then it hit me. Sodomy. I turned and continued home.

You've got to envy the gays. They have a system.

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.