sex diaries

The Rebounding Financial Analyst

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week: the Rebounding Financial Analyst: 24, male, Soho, single, straight.

6 a.m.: Wake up, am viciously hung-over, and decide it’s necessary for a personal day.
9:30 a.m.: Go to deli, flirt with Asian counterworker. She calls me honey like always, and like always, I ignore the big rock on her finger when I picture her naked.
10:29 a.m.: Think about my ex. We were on-again-off-again, and I broke it off four months ago, after two years, because I knew it wouldn’t work out. For the time being, I’m not looking for anything, but I’m not closed off to the possibility.

10:30 a.m.: Facebook my ex, see she’s attending same party as I am on Saturday and desperately hope she doesn’t end up going. She’s winning the breakup, and it’s killing me. Also, because the breakup was 80 percent my fault owing to many issues, including infidelity. When I broke up with her, I knew she was absolutely the girl for me, but my immaturity is not conducive to faithful, long-lasting relationships. Does this make me damaged goods?
3 p.m.: Get Gchat message from former intern who I used to sleep with regularly when she was at the office. Realistically, she was a rebound after I ended things with my ex, but she took “no-strings-attached” to mean that she could like me beyond casual sex. Luckily she lives in Chicago now, so I can get away with one-word responses.
3:40 p.m.: Get a message from a Staten Island girl on dating site. She claims to be a model, a claim about which I am immediately dubious.
5 p.m.: Call hipster girl I’ve seen a couple of times and leave voice mail. She’s cool, and we got along great the two times we’ve been out. See if she’s free tonight for dinner.
11 p.m.: Get out of dinner date, and realize I am horribly awkward while sober on dates. Mental note: have beer before dates. Also realize that despite us getting along, she’s not nearly as good-looking as my ex.
11:05 p.m.: Realize that none of the girls I’ve seen recently are as good-looking as my ex, who I’m still disgustingly infatuated with. Debate whether I subconsciously have lower standards while single, or I’m still self-loathing because I wasn’t a great boyfriend. Decide it’s both. Detour to the liquor store.

10 a.m.: Board flight out of Newark to Florida. Am visiting a platonic friend from college, though I suspect the odds of us hooking up are greater than 50 percent. Plus, the weather blows in the city.
5 p.m.: Finally arrive due to delays. She has a ridiculous place that she’s living in, but she is subletting rooms from an older woman. I’m put in a guest room.
Midnight: At a club, smoking-hot girls everywhere. Debate whether it is kosher to hit on them, even though I’m with a platonic friend.
1:30 a.m.: On way home, making out with college friend.
2 a.m.: Stumble into my guest room, hook up, but no sex. She also does not reciprocate my hand play. How selfish.
2:35 a.m.: After drinking most of liquor-store purchase with roommate, masturbate and finish only through concentration.

1 p.m.: Walking around town, college friend tells me that camel toes are in fashion there. Immediately see three traumatizing examples of this.
5 p.m.: Party at college friend’s house. I was excited when she told me about the gathering, but now, realizing that there’s no booze and the people suck, am much less enthusiastic.
11 p.m.: Go to bed early. Since she doesn’t want to seem like a whore to the older woman who owns the house, she says she’ll come by the guest room when the older woman goes to bed.
2 a.m.: Pissed, she didn’t come by.

11 a.m.: At the beach, drinking beer, in the water, making out with college friend. With all the making out and no sex, I feel as if I’m 16 again.
11 p.m.: Same story as the night before, this time I say I’ll come by her room at 1 a.m.
1 a.m.: HOW IS THIS OLD WOMAN STILL AWAKE? WTF, how can a 50-year-old woman be such a cockblock?

8 p.m.: Back in NYC in time for work. It was a great trip, and I would do it again, even with the zero percent chance of getting ass.
11 p.m.: Too exhausted to beat off, though three nights of non-release is built up.

8:20 a.m.: On way to work, LL Cool J’s “Doin It” comes on my iPod. Realize I haven’t gotten laid regularly since the intern. Again decide to lower my standards.
8 p.m.: Off work, my buddy calls and says, “Let’s drink.” I agree, because I always bow to peer pressure.
11:30 p.m.: Enjoying boys at favorite spot, talking to a girl who I have only the slightest interest in because she seems slutty. Her friend is sloppy drunk, so my girl takes her home, but not before getting my number.
Midnight: She texts asking if we’re still there. I hope she wants me to come over, and respond immediately. No response.
2 a.m.: At another bar, hammered, talking to two new girls with friend. Pissed I got the uglier one. Glance over and see my buddy making out with his girl, and realize I got the prude one, too.
2:01 a.m.: Immediately go in for the kiss. If it’s 2 a.m. on a weeknight, and I’m this hammered, my game really devolves to Swing for the Fences and Hope for the Best. She isn’t totally appalled.

1 p.m.: Gchat with hipster chick from last week. She is noticeably less interested in talking to me than she was on prior occasions, reinforcing my theory that I am more charming when tipsy.
8:30 p.m.: At a buddy’s music show in Brooklyn, a girl with awful teeth starts talking to me. She’s skinny, it’s dark, and I’m getting drunk, so I go along with it. Order another beer.
11 p.m.: At show, aggressively making out with girl. She grabs my groin and ass, I reciprocate enthusiastically.
11:30 p.m.: End of show, try to get her to come home with me (she’s visiting NYC and staying in New Jersey), but she balks. I bail, and give her my number. Unless she quickly changes her mind on the subject of fucking, I doubt I’ll answer if she calls.
Midnight: After make-out session, restrain myself from sending texts to former hookups. Instead, masturbate before sleep.

TOTALS: Two acts of masturbation; five acts of making out with three women; zero acts of intercourse; two valiant late-night attempts to hook up with college friend, valiantly aborted thanks to middle-aged homeowner’s sleep schedule.

The Rebounding Financial Analyst