The Sex Diaries

Reputedly, New York is the sexiest city on earth, a place of beautiful women, powerful men, and lots of hotels. Whole industries are predicated on this state of affairs: Real estate is the ultimate aphrodisiac, the nightlife never stops pumping, and fashion is, after all, a technology of seduction. Everyone looks great, but is anyone really getting laid around here?

We asked six New Yorkers—from a recent college grad to a sexually frustrated father of three—to track every sexual encounter, thought, and arousal for a week. Here’s what their examples showed us: exactly how gay cruising works, that white-collar professionals do indeed masturbate in the office bathroom, and that subway rides are primarily spent fantasizing about co-riders. The young’uns are far more insecure about being single than are thirtysomethings, and it seems that the urbanites with kids are having more sex than singles. Yes, you read that correctly: Shacking up, even with little devils, greatly increases your action. Because even the sluttiest young single spends the majority of his or her nights alone. Here’s how the city that never sleeps, sleeps around.

Illustrations by Omnivore

THE TOTALLY SINGLE, VAGUELY ALCOHOLIC RECENT COLLEGE GRAD WITH A ROOMMATE
Female, 23, publishing assistant, straight and single.

DAY 1
7:30 P.M. Best friend calls and recounts the “out-of-body experience” of her wedding-dress fitting. I am simultaneously jealous and totally grossed out.
7:50 Sister calls and makes excuses for her husband’s weirdness at dinner last night. I don’t want to have to make excuses for anyone else.
10:58 Roommate finally comes home from last night’s date. Hate her. Can’t even look at her.
11:20 Roommate catalogues every second in hot and heavy detail. Hate her more. Go to my room.
11:45 Details of roommate’s date find their way into my fantasy. Is stealing other people’s sex lives wrong? Decide it’s no worse than porn. Proceed.

DAY 2
7:15 A.M. Wonder if roommate can hear vibrator through thin wall. I can’t hear hers. Guess not.
7:35 Shower, dress. Party tonight after work. Woke up too late for cuteness.
10:08 Sister calls, gushes about some new guy to set me up with. Experience with sister tells me that a ton of compliments equals ugly.
6:00 P.M. Babysitting. Seven-year-old: “Are you married?” Jesus Christ.
7:45 Meet friend and brother. Cute brother.
8:15 I have this problem: I meet a guy and instantly gauge our potential sex life. All signs with cute brother point to a decidedly vanilla future.
9:02 Begin to drink too much.

DAY 3
7:15 A.M. Am an ass. Had far too much wine and got blackout-drunk. Can’t remember anything. Thankfully am in own bed. Alone. Inventory: Phone? Check. iPod? Check. Keys? Check. Wallet? Wallet? No wallet.
9:05 Meet friend in front of work. She went home with an older man. She also lost her wallet. Maybe I am not the only idiot in the world.
10:30 E-mail cute brother. Admit defeat, apologize for behavior. Am told I kept touching his face while talking to him. Like, a lot. Cute brother uses the word eccentric to describe me. Am mortified.
11:00 A.M.–4:59 P.M. Mortification.
5:01 Flashback: I made out with a stranger. Perhaps he stole my wallet? He did not give me his number. Not surprised.

DAY 4
9:00 A.M. Decide not to e-mail cute brother anymore.
1:15 P.M. Lunch with engaged best friend. Friend, 23. Fiancé, 38. Resolve never to marry for money.
5:30 L train. Pregnant girl: “Eric and I are too in love to have a plan right now, y’know?” You’re pregnant! You need to have a plan!
5:45 C train. Pretty blonde: “I lovelovelove not working. Being married is the best.” Friend, “I know. You want to go to yoga tomorrow around eleven?”
10:45 P.M. Text old boyfriend comment about Lost. “Worst episode ever!” No response.
11:10 Still no response. Spiraling into freak-out of new girlfriends, reasons he hates me, me being lame and desperate. Give up. Bed.

DAY 5
7:35 A.M. Text from ex: “Seriously. What a waste of an hour!” Maybe am not the biggest loser on the planet.
5:58 P.M. Straight home after work; have grounded myself after Monday’s debacle. Fix drink, snack; put in movie.
6:15 Friend calls. “Can I come over? I’ll bring beers.”
6:40 Let friend in. Cute friend. Used to sleep with friend. Friend holds my hand up six flights to my door. Realize any attraction is long gone.
8:00 Friend out the door.

DAY 6
12:30 P.M. E-mail from cute brother.
7:00 Dinner with roommate and friend. All tables are filled with couples holding hands and kissing.
7:40 I notice the couple to my left has not finished one round of drinks in 40 minutes. It’s true—couples don’t drink as much as singles! If I had a boyfriend, I wouldn’t have blacked out and lost my wallet!

DAY 7
2:45 P.M. Brunch. Meet friend-of-friend publicist who has been touted as “perfect for me.” He’s a name-dropping, social-climbing ass.
3:45 P.M. He goes to the bathroom. I give his business card to the waitress, who’s been eyeing him.
5:00 Drunkenness ensues.

Total: Two acts of masturbation, one makeout session.

THE SEXUALLY FRUSTRATED DAD
Male, 43, Wall Street trader, Bay Ridge, married, three kids.

DAY 1
7:00 A.M. Wake up feeling frisky. My wife says, “Let’s all go to early Mass.”
7:30 P.M. She tells me she really wants to make love with me. It’s too early; the kids are still up.
9:30 She says she’s tired, just snuggles, and falls asleep. Oh, well.

DAY 2
7:00 A.M. Wake up kind of excited, but it’s time to get everybody up.
7:15 Get a nice flash of tits before my wife goes into bathroom.
9:00 P.M. Been a long day and I really want her, but she won’t be home from work for three more hours.
MIDNIGHT Think I said good night to her. May have dreamed it.

DAY 3
6:30 A.M. Awake to put on coffee. She is comatose.
4:00 P.M. Go for a drink. See a bartender friend. She is really hot, but not my wife.
8:00 Home and missing her—another late night.

DAY 4
6:55 A.M. Bring wife coffee in bed. Get a nice kiss for it.
4:00 P.M. Stop for a drink again.
7:45 Surprise! She is home early.
9:00 This is going to be a good night. It is. To be blunt, we have oral sex, both of us, one at a time, then sex with her on top.

DAY 5
7:00 A.M. Get up to make coffee with a big smile on my face. Bring it up to her and give her a big kiss.
11:30 P.M. Manage to wait up for her. Ask if she wants to fool around. Can’t. She got her period this afternoon.

DAY 6
7:00 A.M. Coffee and kiss.
5:00 P.M. Exchange a few playful e-mails with her, even though it’s not going anywhere.
MIDNIGHT Get a good-night kiss.

DAY 7
7:00 A.M. Awake to get bagels, and then we go separate ways with kids.
5:30 P.M. One hour till dinner guests. Frantically cooking.
11:15 Her friends finally leave. We clean up, kiss, and go to sleep.

Total: One act of fellatio; one act of cunnilingus; one act of intercourse, woman on top.

THE WEST VILLAGE CRUISER
Male, 38, magazine editor, West Village, single and gay.

DAY 1
8:00 P.M. Attend 12-step meeting. Run into attractive, Über-muscular acquaintance.
10:00 Start sex journal. Could be humbling. Haven’t had sex in … some time.
12:30 A.M. Log on to a recent discovery: Xtube.com. Watch a twentysomething couple having bareback sex.

DAY 2
7:30 A.M. Involved dream about Über-muscular acquaintance. In dream, he takes me to an estate on the Maine coast. Think it’s more of a real-estate fantasy.
11:30 A.M. Text messages:
D: Hi, this is D, we met along the river 2 years ago and went to ur place … Maybe we could meet again I am in ny again and have fun. Ok?
Me: D … Can u refresh my memory? Send a pic to my e-mail.
D: My computer here can not load pics. I m tall brown, 35, more pass. I was walking along the river close to Christopher. I’m French.
Me: Well—why don’t we grab a coffee?
6:30 P.M. Go to gym. Stare shamelessly at two other men in the free-weights area—a humpy blond and a tall Italian. They don’t notice.
8:00 Text from D raises my spirits.
10:00 D shows up. Sweet, moderately cute fashionista. I have no recollection of meeting him. Worse, we both seem to be bottoms. To my relief, he is on his way by 10:15.

DAY 3
10:00 A.M. Walking my dog, I pass a very handsome, tall man with black hair and a black Lab. We smile and nervously say hello. Turn to look at him after a beat. He keeps going.

DAY 4
3:15 P.M. Get out of work early. Would take the dog out but it’s raining. Log on to Manhunt.com instead.
9:30 Take long walk with friend from 12-step meeting. My terrier won’t leave his dachshund alone. Major humping.
12:30 A.M. Xtube.com. Watch a Greek twentysomething undress for someone (presumably older) holding a camera.

DAY 5
8:00 P.M. See The Lives of Others with friend; am nostalgic for an ex in Berlin.
11:00 Friend walks me home to check out a Website; laughs that I left Manhunt on. We make fun of people’s profiles for a while.

DAY 6
1:00 P.M. Am cruised by a cute Jewish guy with a shaved head. We swap numbers and share a chaste peck.
9:00 The cruising guy calls.
9:30 Cruising guy comes over to play Scrabble. I win. We fool around: blow jobs for both of us. He’s not perturbed by my disclosures (sober, HIV-positive, yadda yadda … ), but I doubt there’ll be another date.

DAY 7
5:15 P.M. Go to gym. Chat up hot guy in sauna. He’s friendly but doesn’t seem too interested.
6:00 My dog is, as usual, very interested in me. Wet kiss.

Total: Two acts of masturbation; two acts of fellatio: one given, one received.

THE FRUSTRATED SINGLE GIRL
Female, 27, high-school teacher, Park Slope, straight.

DAY 1
5:45 A.M. Alarm goes off, proving that my Cillian Murphy dream isn’t real. Hit snooze.
7:05 Scan subway for attractive men.
11:55 Hear students talking about their active sex lives in the hallway.
1:00 P.M. Discuss with colleagues whether Leo is hotter in Titanic than in The Departed.
7:00 Talk to a friend on the phone who is fighting with her husband.
8:12 Google pictures of Zach Braff for twenty minutes.

DAY 2
7:00 A.M. Try to think of the last time I had sex. Am sad when I have to use my fingers to count the months.
11:30 Read People magazine on break. Fantasize about Jonathan Rhys Meyers.
3:00 P.M. Spot hot man outside.
3:02 Abort! Man is completely unattractive up close.
5:00 Whistle “Love in an Elevator,” by Aerosmith.
9:00 Browse through personals on Craigslist and am disappointed that all of the men seem either old or disgusting.

DAY 3
8:30 A.M. Have long, inappropriate conversation with male colleague. Am proud of myself for doing as magazines say and practicing flirting on a less attractive man.
NOON Construction worker screams a comment about my ass. I yell obscenities.
2:30 P.M. Read e-mail from a one-night stand from the U.K. Is coming for a visit in May. Put in saved-box.
3:45 Who am I kidding? I respond that I would be happy to “meet up.”
6:00–11:00 Grade papers.

DAY 4
7:00 A.M. On the subway, sitting next to the hottest guy ever. The one day I didn’t have time to shower.
8:35 Eat a doughnut in the faculty room. Feel guilty about it.
NOON On my way to subway, a piece of wood flies in my eye. I will now be single, fat, and blind.
3:00 P.M. Spill water on my blouse. At parent-teacher conference, a student’s father stares at my breasts.
4:00 Look in mirror. Have swollen eye, no makeup, and dirty hair.
9:00 At home, dejected and miserable. Go to bed.

DAY 5
7:15 A.M. Flirt with a cop who pays for my bagel. I give him my number, but more out of obligation, and hope he doesn’t call.
10:30 Talk about dating with my student teacher. She gives me makeup tips.
NOON Eat salad.
7:00 P.M.–1:00 A.M. Girls come over to drink beer, watch girlie movies.

DAY 6
1:30 P.M. Wake up.
9:00 Go to friend’s birthday dinner. Am introduced to countless friends’ new significant others.
9:03 Sit on the side with one other single girl.
10:00 Am tipsy. Begin listing reasons why I am single to a friend’s boyfriend. He sits and listens, obviously afraid to answer.
11:00 Eat my food. Ogle the waiter. Some girl I don’t know tells me that he is too blue-collar. Decide I don’t like her and think bad thoughts.

DAY 7
11:00 A.M. Brunch with girlfriends. One of my friends discusses how she got hit on by an old man in a wheelchair.
8:00 P.M. Talk to my gay cousin about his love life.
9:30 Talk to friend about her new boyfriend. I met him Saturday and he was amazing: a Match.com find.
10:05 Look at Match.com.

Total: No sex all week.

THE POST-STARTER-MARRIAGE DIVORCÉ
Male, 31, advertising executive, Greenpoint, straight and living alone.

DAY 1
MIDNIGHT Start sex diary. Think about having sex with writer of this article.
2:00 A.M. Wonder if I’d end up going home with a random chick at a bar and having sex. Some chick gives me the eye, but I decide to ignore it.
4:00 Walk home from train. Think about masturbating. Don’t do it. Think about scheduled drinks with a girl tomorrow night. Wonder if we’ll end up having sex tomorrow night. Mental note to change my bedsheets tomorrow.
4:20 Consider looking at porn online. Don’t.
NOON Think about masturbating in shower but don’t.
2:00 P.M. Cute blonde was two places in front of me at the grocery store. Look at her lips and think about what it would be like to kiss her and wake up next to her in the morning.
5:00 Masturbate.

DAY 2
2:00 A.M. Hook up with girl that I meet at a club. Friend-of-a-friend. No penetration, oral only.
2:00 P.M. Realize I don’t know this girl’s name. Girl leaves.
4:00 Masturbate after girl leaves.
6:00 Friend comes over for drinks. Some canoodling.
8:00 Friend leaves. A kiss-with-no-tongue good-bye. Is my breath okay?

DAY 3
8:30 A.M. Find condoms in coat from Day 1.
1:15 P.M. Share elevator at work with cute blonde. Think about making out with her.
1:30 Have job interview. Think about all the cute girls I could potentially have sex with.
3:00 Co-worker makes joke about Viagra.
4:30 Erection at work for absolutely no reason. Wasn’t even thinking about sex.
11:15 Girl sends me text. Wants to hang out tonight. I tell her no.
11:20 Get erection while imagining the girl coming over.
11:25 Masturbate.

DAY 4
8:00 A.M. Wake up with erection.
3:30 P.M. Get uncomfortable erection at work. Fantasize about co-worker. What are her nipples like?
3:35 Masturbate in restroom at work.
8:30 Home. Take shower and masturbate.

DAY 5
8:00 A.M. Wake with erection.
10:00 Fantasize about co-worker.
4:00 P.M. Go to gym. Consider masturbating in shower at gym. Wonder how many people have. Gross.
8:00 Watch movie. Think about hard nipples and cold skin.
11:00 Home. Send text to girl from Day 3. Wonder if I can get her to come over for a booty call.
11:30 She’s reading a book. I decide not to ask her.

DAY 6
8:00 A.M. Wake up with erection.
9:30 Fantasize about girl on subway.
MIDNIGHT Get propositioned by girl at bar. Don’t go home with her.

DAY 7
8:00 A.M. Wake up with erection.
9:30 Think about having sex with girl on subway.
MIDNIGHT Flirt with multiple girls at bar. Do not get numbers and do not go home with any of them.

Total: Five acts of masturbation, one act of fellatio.

THE MILF
Straight female, 35, theater director, East Village, mother of a 13-year-old, in long-term relationship.

DAY 1
9:00 A.M. Woke up to the sound of my kid watching South Park a few feet from our bed. Boyfriend Matt chews kid out for this and other pent-up grievances.
NOON Kid goes to meet a friend. I go to work. I miss Matt.
5:00 P.M. Kid and I meet Matt at restaurant. Matt and I stare at each other throughout dinner and kiss every so often.
6:00 Kid goes to meet another friend, so Matt and I walk home alone. We kiss some more while walking. I whack my lip painfully against his front teeth.
11:00 Watch art film with Matt after kid goes to bed. Despite disturbing images of rotting, long-dead prostitute, I give him a blow job, and we have missionary sex.

DAY 2
7:00 A.M. Send kid off to school.
4:00 P.M. Get nails done. Wonder if Matt will think dark red is sexy or trashy. Opt for clear polish.
6:00 Kid is at his dad’s this week. Susan, who lives upstairs, comes over. Her relationship is falling apart. Matt goes to the other room while I listen. I give her a hug and she cries.
MIDNIGHT Make love with Matt: missionary, then doggy style. Nice not to have to do it quietly.

DAY 3
7:00 A.M. Matt wants sex, but I’m too sleepy.
1:00 P.M. One of the first days of spring. Lots of guys look at me hopefully. One says, “Can I walk with you?” I tell him, “No, I’m going to meet my boyfriend.”
2:00 Lunch with Matt. He’s depressed about money worries. Some talk and hand-holding.
11:00 Matt falls asleep stroking my breasts while we are watching a boring indie film.

DAY 4
9:00 A.M. Wake up to find Matt already gone.
4:30 P.M. Surprised to find Matt home. Tired, we lay down to take a nap. Have missionary sex instead.
9:00 We go for a drink at a quiet bar. So nice to spend time with him alone.

DAY 5
9:00 A.M. Cuddle with Matt for too long, rush out late. Forget my cell phone.
6:00 P.M. Kid doesn’t have his viola for his lesson. Called me eight times on my cell, which was at home.
9:00 Meet Matt for dinner in Koreatown.
MIDNIGHT Matt wants me to come to bed, but I get obsessed over finding a modern parallel to Shakespeare for something I’m working on.

DAY 6
9:00 A.M. Wake up to find Matt upset over an old e-mail of mine to a photographer. I’ve posed for a lot of art photographers, but I don’t pose nude anymore because he has an issue about it. Matt upset that I told the photographer this. “Don’t make me out to be petty,” he says.
NOON Would like to call Matt but think he’s still mad at me. The nudity issue crops up every so often.
9:00 P.M. Meet Matt at a bar. Frost of earlier today seems to have melted.

DAY 7
9:00 A.M. Didn’t want to orgasm, but then Matt goes down on me and I reconsider.
8:00 P.M. Go to friend’s father’s birthday party, look at his 50th wedding-anniversary picture. Matt says, “I want to stay with you that long.”

Total: Two makeout sessions; one act of fellatio; one act of cunnilingus; four acts of intercourse: one doggy style, three missionary.

For more sex diaries,
read Daily Intel.

The Sex Diaries