New York’s Sex Diaries series asks anonymous city dwellers to record a week in their sex lives — with comic, tragic, often sexy, and always revealing results. This week, a single woman, 36, film business, straight, Upper West Side.
DAY ONE
9 a.m. “You are so loved.” It’s written on my coffee mug. But am I? Alex, a guy I’ve had about five dates with, is coming over tonight. We’ve never so much as kissed. He is cute — 39, reminds me of Danny Castellano — but seems sexually timid. Every date has ended with teenagerlike awkwardness. Sexual bravado is important, but not everything, right? Anyway, we’ll see how it shakes out tonight.
5 p.m. I’m home early to cook some dinner for Alex — I work in the movie business, on the production side. I’m making eggplant Parm. Bought a nice bottle of wine and fresh flowers, too. Tonight will make it or break it.
6 p.m. Long shower. Shave legs, pits, inner-butt (just in case). Moisturize everywhere.
6:45 p.m. Open the bottle of wine and get the food ready. The wine tastes very, very good.
7 p.m. Alex arrives just on time. He brings another bottle of nice wine. He looks really handsome in his work clothes! He is the CFO of a big sports brand. He lives in the city, but I like his blue-collar New England vibe.
8:30 p.m. We’ve eaten and moved to the couch. He kisses me. FINALLY. He is an amazing kisser! PHEW. The hookup is hot. Our sexual chemistry is off the charts. I never would have imagined? He has major sexual bravado. It’s just my speed. I’m super-wet and turned on. We move to the bedroom. We have great sex. It actually hurts, like pierces, when he enters me. I haven’t had that sensation since I was just learning to have sex 20 years ago. He doesn’t use a condom, which shocks me given he’s a straitlaced kind of guy. I’m not thrilled about the no condom but I have to say, it all felt SO GOOD.
9:30 p.m. We go again. This time, faster, he comes quickly (pulled out, like before), and it’s just as hot. I am still in shock over what a great fuck he is.
10:30 p.m. He leaves … which I’m happy about. Too soon for a sleeper. But, yeah, I like this guy …
DAY TWO
8 a.m. The hell of “Will he text me” ensues. I HATE that feeling. Waiting for a guy to text is misery.
11 a.m. Typical can’t-focus-on-work shit because he hasn’t texted.
1 p.m. Now I’m starting to feel insecure. Did I taste garlicky from the eggplant Parm? Was it in my pores? Was my body not as fit as it appears to be with clothes on? Were my tits a disappointment?
3 p.m. He texts. Nothing crazy CRAZY, but something about enjoying the night very much. I’ll take it. The text-game is so exhausting. I want to say I’m above it all, but I force myself to wait to text back. You just have to.
7 p.m. I text back something medium-sexy. Instead of waiting for him to write back, I just go to sleep early.
DAY THREE
8 a.m. I don’t even want to talk about his lack of texting and how it’s going to consume me all day long.
Noon Go through all the things that could be wrong with my body, personality, apartment, cooking skills, and shaving techniques, all day long.
8 p.m. Shitty day, all day long.
DAY FOUR
11 a.m. He texts a perfectly friendly and sweet text about meeting up tonight at a great restaurant in my neighborhood. What the what? Wow — power move coming from a guy I pretty much felt completely dissed by. Was it all in my head?
1 p.m. I write back saying yes, and he responds immediately with another perfectly friendly and sweet text about timing.
2 p.m. I spend several hours shopping for the right outfit, determined to knock it out of the park tonight so neither of us ever has a moment of doubt that HE wants ME, and not the other way around. I find just the dress I was looking for at Barneys. It is $600 but Fuck It.
8 p.m. I walk into the restaurant, he is there, and he is as adorably Danny Castellano as ever. On top of that, my body now knows how great it fits with his, so I’m all sorts of turned-on. I’m glad I bought the dress, too. I feel pretty amazing. “You are Angelina Jolie!” my best friend texts, like five times in a row.
10 p.m. Back at my place for sex. We do it in the exact same position as last time; it pierces when he enters me again. And like clockwork, I come at the exact same time as last time. So does he. It’s really, really good — not because it’s porn-star sex, at all, but because of the chemistry.
Midnight Kick him out again. He seems smitten. My work is done.
1 a.m. Alas — no text from him saying he made it home or that he had a great night or ANYTHING.
DAY FIVE
Noon THIS AGAIN.
10 p.m. Fucker hasn’t texted me. I’m sorry, but it’s not nice. I don’t want to live like this!
DAY SIX
9 a.m. I’m over this guy. I don’t think it’s cool to have great dates, then hot sex, and then disappear. We’re all busy and modern and whatever, but it’s insensitive. I decide to make plans with another guy tonight.
1 p.m. Good. I have plans with Scott, a sexy ex, tonight. I’d never date him again: He’s a player and kind of a scene-chaser. But he’s always fun to catch up with. We’re going somewhere nice. I want to wear my dress again.
6:30 p.m. Of course, on my way to meet Scott, Alex texts. So fucking predicable, dating. I ignore the text. Let him wait.
8 p.m. Scott tells me he’s seeing someone and that she has him by the balls, basically. I’m happy for him. It’s cool. He seems really into her, like maybe he’s ready to settle down.
10 p.m. As Scott and I share an Uber home he tries to hook up with me. He is somewhat forceful about wanting me to come upstairs with him. Ugh. All of it. Gross. I thought he was into his new girlfriend. The whole thing is just offensive.
11 p.m. The upside is that I never texted Alex back. By the way, I can’t believe I’m in my 30s and this is the shit I still deal with.
DAY SEVEN
10 a.m. I nonchalantly text Alex and invite him to join me for a run in Central Park. He writes back immediately that he’s IN.
Noon At this point I’m so over all these guys that I show up for our run just wanting to run. Not win anyone over, not test anyone — just run.
12:30 p.m. Alex kisses me hello on the lips. Very boyfriend-ly. We run three miles. It feels nice: the sweat, the air, the conversation, the companionship … I like it all very much, so much that it scares me a little.
2 p.m. We get lunch and I say I have to go home soon because I have friends in town. Partly true — I have to go home because my underwear is so sweaty I’m afraid I’ll get a yeast infection. Alex hints about tagging along with us later, but I push him away saying it’s not his kind of scene.
7 p.m. I’m with my friends. No text from Alex. My mind drifts to how sweaty and ugly I probably looked during our lunch. This guy makes me feel insecure. Or maybe I make myself feel insecure. I tell my friends I need to find a therapist.
10 p.m. He never texted. He probably will tomorrow. I can’t read this guy and kind of want to cut my losses. But … the sex.
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