sex diaries

The College Student Dating Older Men

Once a week, Daily Intel looks behind doors left slightly ajar. The College Student Dating Older Men: 20, female, Manhattan, single, straight.

Day One
12:03 a.m.: Ex–Pseudo Boyfriend responds to a mass e-mail I’ve just sent out to tell me I left some clothes at his place. We’ve just ended an eight-month on-and-off hook-up. We had the best sex I’ve ever had. And not much else.
12:04 a.m.: Start to think about times spent with him, which makes me horny. Too bad he’s hundreds of miles away.
12:08 a.m.: Worrying. My worries: adjusting to New York dating, which means meeting guys in places other than frats, and thus being less drunk than I would be normally. And that I’m not gonna find a guy who is as good in bed as Ex-Pseudo. I have no idea what I’m looking for, but I’m definitely looking.

11:44 a.m.: At work. Thirty-year-old Lawyer Dude I met last week at a bar and then had coffee with. He texts me to see if we’re still on for dinner tomorrow night.
2:47 p.m.: Lawyer Dude texts again to ask if I want to get dinner tonight instead of tomorrow night, but I already have dinner plans with a girlfriend.
6:28 p.m.: Lawyer Dude e-mails me asking if I plan on going out after dinner. I say probably not, because I’m tired. Christ, he is starting to seem a little too eager to hang out. When attractive and successful guys act this eager, I assume something must be a little off about them. This probably explains why I’ve spent the past eight months having tons of sex with the most unattractive, out-of-shape successful guy possible.
7:30 p.m.: Dinner with my friend at an adorable Belgian café in the village. She tells me about how she was really attracted to this guy and wanted to have sex with him, but when the time came she couldn’t metaphorically get it up (this is what we say when we have a hard time getting in the mood).
11 p.m.: On the subway home I see a cute guy, who sits directly across from me when the car is empty. We make flirtatious eye contact. I entertain the idea of spontaneously leaving my name and number, but in reality would never actually do that.

7:25 a.m.: Lawyer Dude e-mails me asking how dinner was last night and confirming that we’re still on tonight for the millionth time.
7:37 a.m.: I wait till the message comes through on my BlackBerry so I have an excuse to give a one-word response.
3:45 p.m.: The day could not be more slow. So I fantasize about Ex-Pseudo pinning my hands above my head and having his way with me.
6:20 p.m.: Meet Lawyer Dude for a pre-dinner drink downtown.
7:15 p.m.: Beginning to feel weird about the age difference when I realize that he’s not even an eighties baby. He asks me if I’m having a good time for the third time tonight, which is starting to irritate me.
8:30 p.m.: It’s freezing out, so he suggests we take a cab to a bar. I realize this is just his way of making a move on me as he goes in for the kiss almost immediately. I’m attracted to him, but kissing him feels awkward. Maybe this is because I’ve only had three glasses of wine so far. I need to grow up.
9 p.m. : He invites me back to his apartment and I tell him I can’t because I have to get up early for work, which is somewhat true. He asks if we’ll hang out again and I say I don’t know, that I’m a little weirded out by the age difference. I try to convince him that I’m not worth his time but that path doesn’t work really, so I flat-out tell him that I’m still incredibly immature and that doesn’t seem to bother him either. I tell him I need to sleep on this.

6 p.m.: Arrive home from work and [find] my roommate Vanessa. She tells me that her old friend is visiting and that we have to show him a good time.
10:15 p.m.: Head to a dive bar with Vanessa and her friend, who is actually pretty cute. I’m not sure whether she is interested in him, though, so I don’t flirt with him. Vanessa sits in between us. A creepy, greasy man sits on the other side of me and attempts to initiate conversation. I have no problem acting unfriendly. I don’t believe in karma.
10:40 p.m.: Greasy Man finally gets up and leaves, and a cute guy in a green polo asks if he can take the seat. Pleasant conversation.
11 p.m.: Decide I’m not that interested. I don’t like guys who are really into tattoos and keep talking about all the ones they want to get. He didn’t seem very intelligent either. I tell Vanessa and her friend good night and head home to bed.
11:17 p.m.: Old friend texts me … we used to have a lot of sexual tension but nothing ever happened. We make plans to hang out this weekend. I wonder if it will be completely platonic as usual.
11:30 p.m.: Realize this is one of the few nights I’ll have the apartment to myself, so I decide to try to get myself off before bed, but fall asleep.
12:22 a.m.: Wake up to a buzzing BlackBerry, with my hand down my pants. It’s a booty text from a guy I haven’t hooked up with in about four years.

11 a.m.: Cute guy in my office walks by my cubicle for the fifth time that morning, each time making brief eye contact.
1 p.m.: I hear him talking in the kitchen later and decide he has an annoying voice. I need to be less critical.
1:31 p.m.: John, my high-school sweetheart and the only guy I’ve ever been in love with, sends me a long e-mail apologizing for the way things were left off between us. Our relationship had been going really well, but I didn’t want to be in a committed long-distance relationship throughout my entire college experience, so after freshmen year we called it quits. We had always been together over summer and winter vacation, but then he said it was too hard for him to do it this year if we weren’t dating anymore, which upset me.

2:13 a.m.: Ex-Pseudo’s best friend, who is also one of my closest friends, drunk dials me telling me how much he misses me. He does this frequently when he’s drunk. He’s a known man whore and I am essentially his emotional booty call. We had a brief affair behind Pseudo’s back, but he messed up badly and I’ve put him in the “just friends” category ever since.
10 a.m.: Brunch with two of my closest high-school girlfriends. My one friend has been dating the same guy since freshmen year of high school. She sickens me.
9 p.m.: Bar-hopping with my other roommate, Steven, who is my only legitimately platonic guy friend (no attraction on either side). He is, of the four, also the only one I’ve never been involved with.
9:30 p.m.: Steve observes that we are probably not very approachable since it looks like we’re on a date.
11 p.m.: We head to an apartment party with people from college. Most of the guys there are frat brothers of Ex-Pseudo, leaving me essentially off-limits … oh well. Everyone is a lot friendlier when thrown together in the big city.
12:20 a.m.: Leave the party alone and drunk dial Ex-Pseudo’s man-whore best friend, but he doesn’t answer. I am at a point in life where I am afraid to sleep with guys I really care about because I’m afraid they won’t treat me as well after. I never had anything to lose with Ex-Pseudo.

10:30 a.m.: Wake up with possibly the worst hangover I’ve ever had. Steven and I decide to get some fresh air and brunch to nurse our hangovers. Miserable morning.
9:30 p.m.: Meet up with some girlfriends at a bar nearby. It’s full of couples canoodling in the dark corners. Jealous.

9:15 a.m.: There are so many hot guys on the floor below mine. I should have picked a different department.
4:30 p.m.: Text from best guy friend from high school. I had a crush on him for the longest time, and then we had the most anticlimactic hook-up ever. He might be coming to visit. I don’t offer my couch because I don’t want him to think I’m trying to hook up with him. I don’t want any confusion.

TOTALS: Two acts of masturbation, one aborted; one makeout with Lawyer Dude; zero acts of intercourse; two received, and ignored, booty-call text messages; numerous texts with former hook-ups.

The College Student Dating Older Men