sex diaries

The College Dropout Hooking Up With a Spoiled Brat From OkCupid

Once a week, Daily Intel takes a peek behind doors left slightly ajar. This week, the College Dropout Hooking Up With a Spoiled Brat From OkCupid: Female, 22, Fairfield County, Connecticut, former Ivy League student/current couch potato, single, straight.


10 a.m. My dog barking at the neighbors wakes me up. I just relocated to my parents’ house after a hasty decision to take time off from my Ivy League premed education for personal reasons. I think I was just ready for a hiatus from the constant pressure, crippling anxiety about med school, and a variety of issues with my roommates; plus, after a painful breakup last year, I still don’t really feel like myself. I’ve always been a straight arrow, but this week, I’ve been doing a whole lot of nothing and trying to forget that there’s anything wrong, mostly with the help of sweet, heavenly cannabis. I feel totally lost and know I need to get it together soon, but I’m trying to just let things ride for the time being.

4:15 p.m. Am walking the dog and start thinking how lonely I will be over the next few months, since I know almost no one in town. All of my college friends are still back there, and nearly all of my friends from high school are elsewhere. The dating scene at my school pretty much consisted of going to this one bar and hoping for the best, and I don’t know how well that strategy will work in the suburbs. Have the brilliant idea of creating an OkCupid profile to meet people. Had previously been a little skeeved out by online dating but am now curious. A friend had a decent experience for a few months in another city using it. Guess I’m jumping in.

5 p.m. I’m kind of into this. Already got five messages! This will be entertaining


 4 p.m. Talking a little bit with a few guys on OkCupid that seem like they wouldn’t be too horrible to meet in person. I’ve gotten more than 50 messages but have only responded to eight guys. My somewhat arbitrary criteria are guys who (a) don’t have any mirror pictures, (b) have intelligible and interesting profiles, and (c) write something that makes it clear they actually read/related to my profile or that actually makes me laugh. This website is so self-indulgent and creepy. I also have no idea how to date, in general, because my love life was basically a series of semiserious relationships until last year. I think I went on three “real dates” in all of college, and that’s probably more dates than 90 percent of my friends, so I feel like a fish out of water. At the very least I’m enjoying the flattery, and casual dating might be a good way to keep myself busy.

6 p.m. Call Boy Toy/Dealer. He lives in Connecticut, and we spent the last few weeks I was home over the summer smoking and having sex for hours at a time. I used to firmly think that sex without love could never be as good, but he cleared me of that misconception pretty quickly, and we always had a lot of fun together. He has a black Jeep, and I think about texting him to suggest that he do me in there, but I restrain myself. We’ve only hooked up a handful of times, but for some reason, we’ve really been spanning locations: shower, floor, etc. I’ve talked to him pretty recently, but he’s definitely being dodgy, and I don’t know why. He doesn’t answer or call back. I’m pretty bummed, since I could really use a friend with benefits to waste time with. I just want to smoke, screw, and bake away all of my problems.


11 p.m. Notice that a few of my “recent visitors” on OkCupid are of the female variety. Start thinking about the hypothetical possibility of talking to other girls in a not strictly platonic way. I’ve never been seriously interested in the same sex, but I guess the possibility intrigues me, especially because I only ever masturbate to lesbian porn. I’m not sure if this is normal, because I would never talk to most of my (uptight) friends from school about this stuff, but I’m probably not going to act on it anyway.


5 p.m. Text Paralegal looking to spend a night away from my well-meaning but suffocating parents by going into the city to his apartment. He invites me to sleep over and hang out with him. Done. We’ve had an on and off friendship since high school, but we’re really close, and consequently I put up with a lot of stuff I shouldn’t. He always flakes on plans and generally tries to be as emotionally distant as possible, although I have elicited a few “I love you“‘s in the past. He’s also the first guy I ever went down on (junior year of high school in my car at 2 a.m.), so I have a special place in my heart for him. We’ve drunkenly hooked up a couple of times since then but held off on sex because we both know it would change everything. Nothing has happened between us in the past few years though. Fib to my parents about who I’m visiting in the city.

10 p.m. I give him some of his favorite cheese when I get there (I always make fun of him because he only eats Muenster) mostly as a joke, and after some mild awkwardness, we are on his couch watching TV and drinking whiskey. His friend comes over to join us, tequila shots ensue, and we go out.

1 a.m. Back in his apartment smoking weed and watching Game of Thrones. I try to control myself, but it only takes a few minutes before I climb on top of him. Things move into his bedroom, and we’re both verryyyy sloppy. Clothes are off. I make him turn on the National and run my hard nipples up and down his back. At some point, we mumble words back and forth about a condom, but all of a sudden, he goes soft and says he doesn’t want to have sex. I try to go down on him to help things along. Nope. WTF? I sleep on the couch, pissed off but surprisingly comfy at least.


9 a.m. Feeling silly about last night, I go back into his bed to try to reconcile, assuming we will have morning sex. I attempt to subtly grind my butt against him. He’s not having it. I get really confused and upset. Go back outside to think. Mildly freak out. Wonder if he might be gay. We have always been really close, and I know he is attracted to me, and now he won’t close the deal despite my obvious hints. After I basically drag enough information out of him, he reluctantly admits he has been seeing someone and doesn’t want to do “the wrong thing.” I am livid and somewhat heartbroken. I steal some of his weed on my way out the door, out of spite and necessity. Whoever claims that females aren’t affected by blue balls is an idiot.

11 a.m. Walking around Grand Central, dazed and confused, mango juice in one hand and coffee in the other. I realize I left my ID, debit card, and $40 at his apartment. I had them stuffed in my bra because of a lack of pockets, and they probably fell under his bed last night. Text him and ask him to mail them to my parents’ house ASAP. I am such a mess.

Noon Angry and at new heights of sexual frustration, I go through my phone and text a few people I know in the city to delay going home to my parents. My options are seriously dwindling, but on a total whim, I text two alumni from my school that have told me to “text them if I’m ever in New York.” Investment Banker is a 2011 grad I hooked up with during homecoming a few weeks ago, and McDonald’s Guy I met last year at a bar. We shared some romantic Chicken McNuggets but never hooked up and have loosely kept in touch even though he’s seven years older. Investment Banker is working all day. McDonald’s Guy invites me to walk his dog in Central Park with him in a few hours, but I don’t feel like waiting around. Guess I’m on the abstinent train to Connecticut — lucky me! Ask McDonald’s Guy for a rain check, but I can’t tell if seeing him would be too weird even for me.

1 p.m. Text and Snapchat the whole way home with a guy from OkCupid, a D.J. I may actually be interested in because we’ve been talking for a few days and he seems funny and normal and cool. Clearly it is time for me to move on from the guys of my past. He wants to watch a movie and smoke, and I’m reasonably confident he’s not a creep or psycho, so we’re on.

7:30 p.m. After making stuffed chicken breasts for my family for lack of anything better to do, heading to the D.J.’s house to watch Savages. Panic on the way over that he will either be 40 and bald, or a dangerous psychopath.

8 p.m. Pull up to a huge mansion. He’s 24 and lives in his parents’ guest house, which has a life-size racing game and his studio inside. Is this a joke?

8:20 p.m.We smoke a little and start to watch the movie. Casual cuddling ensues. I haven’t done this since high school. First an arm around me, then hands under my sweatshirt and under my jeans.

9 p.m. I make him turn off the lights and TV and put on music because I am so not feeling Blake Lively’s annoying voice in the background. He fingers me for a few minutes, and I’m fully intending to lose myself in whatever happens, but I soon realize it’s getting late and I have an early day tomorrow, and I’m also a little freaked out since I hardly know this guy and am still bummed about HSF.

9:20 p.m. Make excuses to leave, and feel weird about the un-reciprocated, non-climaxing one-sided touching. Why is there no protocol for these situations? Go home feeling exhausted, a little depressed, and equally frustrated.


10 a.m. Text from D.J. Not sure if I wasn’t feeling last night because of him or because of me, so I hold off on texting him back for now.

2 p.m. Make a date with someone from OkCupid who has tons of shared interests. We’re going to hike and smoke, and I’m sure it’ll be fun, but I’m still pretty apprehensive about this whole concept. My main concern with this site after last night is that I don’t have a good indicator for whether or not I’ll be attracted to the guys, either because they aren’t accurately represented or because it’s just complicated. Wish I had a way to tell if a guy was going to be good in bed or not. The jury is still out on whether this profile will last another week, but at least I’ve gotten some entertainment and weed out of it.

5 p.m. The potential for new guys in my life has made me think about my ex a lot. We dated for a year when I was a sophomore, and I was nuts about him. Things were so effortless when we started hanging out that I never thought twice about it, and the sex was always great. Sometimes I still really miss what we had, and it doesn’t seem fair that it can be so hard to find. Plus, I think the regular orgasms were keeping me sane.

10 p.m. Catchup Skyping with ex. Still feel so warm and fuzzy about him even though it’s been a while. Kick myself for deciding it was a good idea to catch up.


5 p.m. Text from D.J. He wants to hang out later. Since I’m still a simmering pot of sexual frustration, I bite.

10 p.m. Pull up to his house, and he’s smoking a cigarette on his balcony. We go to his studio, and he packs a bowl and attempts to teach me about electronic music.

10:30 p.m. We move to his bed, and I take off his shoes and straddle him. I guess the mood was off last time, because this time I’m totally engrossed and loving every second. He gets me off with his hands first and then enters me torturously slowly. He comes all over me. Bliss. I can’t exactly put my finger on why sex is so much better high, but every sensation seems like it’s magnified, and I’ve been needing a cathartic orgasm all week. Plus, it’s nice to be with a guy who at least mostly knows what he’s doing (probably because he’s older, but maybe because he’s a manwhore? I’m used to the bare minimum of skills from wasted “frat bros” my age).

Midnight He goes outside to smoke a cigarette, and I decide I want one because Boy Toy once said he smokes them after sex to “calm his s—t down.” It’s not that great. Also realize that this guy is kind of a jerk, not to mention a spoiled brat, but I’m not sure I care.

12:30 a.m. On his couch, barely touching, but I’m still so turned on, I initiate round two. He pulls my hair, and I lose my mind. This time he comes in my mouth.

2 a.m. Back in my own bed, still kind of reeling from before and too jittery to sleep, I find some trashy porn on RedTube and try to get off as quietly as possible (can’t shatter my parents’ image of their perfect little girl!). Repeat three times and pass out.

TOTALS: 2 acts of masturbation; 1 act of cuddling; 2 acts of manual stimulation (received); 1 act of fellatio; 2 acts of intercourse; 2 rebuffed offers of sex; 3 acts of smoking pot.

OkCupid Sex Diary