sex diaries

The Single Grad Student With an NSA Buddy and a Roommate Dating a Total Loser

Once a week, Daily Intel takes a peek behind doors left slightly ajar: This week, the Single Grad Student With an NSA Buddy and a Roommate Dating a Total Loser: 32, Park Slope, graduate student, straight, male, single.

8:45 a.m.: Catch a sexy smile from this Joan Jett–looking young woman that I’ve seen a couple of times on the train, instantly wiping away any residual sleepiness that my morning coffee failed to stamp out.
8:50 a.m.: After several furtive glances confirming that she wasn’t actually looking at someone else, I tell myself I should to talk to this girl, which of course I don’t. Spend the rest of the ride rationalizing and debating with myself why I didn’t talk to her. Final verdict: I’m a coward.
11 p.m.: Get home after dinner and drinks with a friend to find my roommate and her recent boyfriend hanging out in the living room. I’m distracted by how many empty beer cans are on the table and by how much I can’t believe she’s with this guy: not handsome, not in shape, not employed, and not in control of his drinking problem. I excuse myself.
11:30 p.m.: My roommate and her boyfriend get ready to go to sleep in the bedroom next door. Everything can be heard through our paper-thin walls. I’m hoping for one of those nights where he’s too drunk to get it up so I am spared the noise.
11:45 p.m.: The familiar loud thumping of my roommate’s headboard slamming against our shared wall as her boyfriend frantically pounds out his three minutes of glory.
11:47 p.m.: Thinking that I really ought to ask my roommate to move her bed away from the wall a little.
11:48 p.m.: Right on schedule, thumping ceases; shelves and their contents thankfully intact.

1:30 p.m.: Get an e-mail from a PR rep I met online asking if we’re still on for tomorrow night. I write back to confirm and give her my number.
7 p.m.: Get home and decide to stay in for the night. I’ve been spending too much money out lately.
8:30 p.m.: Start trolling a dating site for possible connections.
10:30 p.m.: Horrified that I’ve spent two hours mindlessly scanning this stupid site. Think it might be time to abandon my experiment with online dating.
Midnight: Jerk off before bed to half-baked fantasy I concoct involving Joan Jett lady.

8:40 a.m.: Make sure to get on the same subway car in hopes of seeing Joan Jett. She’s not on the train.
2 p.m.: Receive text from the PR rep suggesting that we hit up a bar she knows for happy-hour drinks. Does 6:30 work? Sounds good to me.
6:30 p.m.: Meet the PR rep at a downtown bar. Encouraging signs at the start: She’s cute, confident, and instantly warm.
6:32 p.m.: We grab beer at the bar, then find a table in the back.
6:33 p.m.: PR rep suddenly looks as if she’s seen a ghost. Two tables away sits her best friend’s recent ex-boyfriend with another woman. She calls to him, and he sidles slowly over. Very awkward introductions, followed by even more awkward chitchat.
6:45 p.m.: It’s clear that the PR rep is more interested in keeping tabs on the ex-boyfriend’s date than attending to her own. She keeps stealing narrow-eyed looks across the room while I essentially carry on a conversation with myself.
7 p.m.: Best friend’s ex-boyfriend and his new lady love leave.
7:15 p.m.: Things aren’t better now that he’s gone. She’s doing her share of the talking, but it’s all about what a jerk he is. Time to pull the plug on this disaster.
7:30 p.m.: After walking the PR rep to her train stop, I head home, relieved when I get there to find an empty apartment.
8:30 p.m.: Trying to decide which online experience was worse: tonight’s, or the one with the woman who confessed to sleeping with her college professor freshman year, breaking up his marriage and then contemplating killing herself when he broke things off. Decide to quit online dating.
12:15 p.m.: Consider masturbating, but feeling worn out and disappointed from this latest online train wreck.

8:40 a.m.: Intentionally do not get on the same subway car as before. Joan Jett is not on this one either.
12:30 p.m.: Get a call from the Persian Princess, an old friend and occasional no-strings-attached sex buddy, wanting to know if I feel like getting together over the weekend at her place to watch a movie. We’ve been watching movies together regularly over the past several months since we both became single again. We make a tentative plan for tomorrow night.
7 p.m.: Meet a buddy of mine for dinner at a midtown Irish pub. I thought I had problems, but no: My friend’s dating a woman whose last boyfriend had a nine-inch penis, and hasn’t seemed to get over it. As a result, he can’t get over it either, and has developed a robust inferiority complex. “How do you compete with that?” he says plaintively between sips of beer.
11:30 p.m.: Return home with a healthy buzz. Scour dating site for possible matches. So much for resolute decision making.
Midnight: Roommate and her boyfriend return from a night out. Waiting for the love thumps to start.
12:30 a.m.: Nothing. Must be passed out.

3 p.m.: Get e-mail from friend in L.A. lamenting the fact that I’m not able to make it to Vegas this weekend for his bachelor party. I’m thrilled not to be going. I hate Vegas.
8 p.m.: Trek from Brooklyn to the Persian Princess’s Upper West Side apartment. Once there, I sit in the living room looking through the small stack of DVDs the Double P has rented while she prepares a couple of vodka sodas in the kitchen.
9 p.m.: After chatting on the couch for a bit, the Double P throws in Goya’s Ghosts, an immediately unbearable movie, not to mention a strange choice for getting in the mood.
9:30 p.m.: We have a few laughs poking fun at the film, which soon turns into kissing, followed shortly by some petting before she goes down on me.
10 p.m.: We move from the living room to her bedroom. Sex with the Double P has gotten great recently, and she’s been increasingly assertive. Tonight she introduces really hard biting into the mix, a nice surprise.
1 a.m.: Pillow talk takes unexpected turn when the Double P announces that she wants me to spend time with her and her parents when they visit next week. I’m not sure what to make of this request.
1:15 a.m.: The increasing use of “us” in this conversation is making me nervous. This is precisely the sort of thing we agreed would not feature in our arrangement.
1:20 a.m.: Begin feeling the urgent need to get dressed and go back home before I hear any more.
1:25 a.m.: Impulse to run away instantly crushed as the Double P begins massaging my penis until I get hard, a prelude to round two.

11 a.m.: Wake up with a slight headache. The Double P wants to go for brunch, possibly with friends. I beg off, telling her that I have a lot I need to get done today, which is true, but of course I have absolutely no intention of actually doing half of it.
1:30 p.m.: Back at my apartment. Thinking back on last night with a mixture of pleasure and mild emotional discomfort.
3 p.m.: Receive text from the Double P telling me again how much she enjoyed last night. This is another first. Ugh.
3:01 p.m.: Decide that the Double P and I need to have a talk about where things are going. True to male form, I avoid having talks like the plague, and decide not to deal with this one right now.
9 p.m.: Meet friends for beer at a downtown dive.
9:45 p.m.: Let call from the Double P go directly to voice mail.
12:30 a.m.: Make drunken eyes at a girl down the bar. She wants nothing to do with me.
2:30 a.m.: Head back to Brooklyn by my lonesome.

5 a.m.: Woken up by the incessant buzzing of my BlackBerry. Waiting for me are a series of texted pictures from the party in Vegas, including one of my friend half-naked and sporting gigantic red sunglasses sprawled on a bed washing himself with $50 bills. I don’t even want to know.
5:15 a.m.: Still awake. Contemplate masturbating, but can’t muster the energy. Think I still may be drunk.
5:30 a.m.: Get out of bed to use the bathroom. Confirm that I am indeed still drunk.
7:30 p.m.: Receive e-mail from a teacher via the dating site. It’s quite witty and easygoing.
7:35 p.m.: Check teacher’s profile on dating site. She’s attractive and apparently able to distinguish between ‘there,’ ‘their,’ and ‘they’re,’ a rare talent among those prowling the web for love. Maybe there’s hope there after all.
7:40 p.m.: Send return message.

TOTALS: Two acts of intercourse with unfortunately strings-attached buddy; one act of fellatio; one act of masturbation; two aborted acts of masturbation; one disastrous blind online date.

The Single Grad Student With an NSA Buddy and a Roommate Dating a Total Loser