sex diaries

The Architect Who Doesn’t Know What He’s Doing Wrong

Photo: Getty Images

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 40-year-old architect who lets an almost-famous girl smoke in his living room. Straight, single, West Village.


9:00 a.m. Let’s call her Cassie. Cassie is hungover and looks like shit, but in a hot way. The way Kristen Stewart can look like shit. And apparently she can’t get out of here fast enough. No morning sex. No scrambled eggs. Not a good sign. I am a shit lover — I know it.

10:30 a.m. I sit at my computer in my “den,” trying to work. I’m an architect and work from home. I’m hungover too, which doesn’t help the self-hatred. Maybe I should try hypnosis. Because this always happens: I meet a girl slightly out of my league, I charm her with my charms, we drink the drinks, we have the sex, and then she gets the fuck out of Dodge without ever looking back. Cassie will be no different.

2:00 p.m. Do I have halitosis? Is my penis that small? I am almost positive it is slightly above average, but what the hell do I know? Am I repulsive in a way I do not realize, such as eating like a beast or slouching like I’m sickly? What aren’t these women telling me?

9:00 p.m. I text Cassie.

Midnight She hasn’t returned my text. Shocker.


10:00 a.m. Therapy just ended. I will say: I think my therapist wants me. There’s one for the taking. We talked about my ex-fiancée. Mind you, this was an engagement that ended almost a decade ago. I don’t long for my ex (so 2011!), but I’m constantly hung up on what makes me so deplorable. I’m tall. I have (mostly) all of my hair. I’ve got cash. Girls say I look like Andrew McCarthy. Or is it James Spader? No, McCarthy. Obviously, I never felt loved enough by my Wasp-tastic family, but they weren’t so bad either.

Noon I have a burger with a female friend, Jayne. We are quite fond of our love-sucks-and-then-you-die lunches. Jayne is in a sick-and-twisted, three-year (!!!) relationship with a neighbor who likes to fuck her in the ass and ignore her on the street. Seriously. She can’t quit him. We agree that at least her issues are worse than mine.

6:00 p.m. I have a date from the app Raya. We decide to meet at a wine bar in the West Village. I recognize her when she comes in: She is a famous person’s daughter. I only know this because I worked on her father’s house. Interesting. We kiss hello, and I can smell cigarettes on her. Who smokes in 100-degree weather? Only a sexy AF train-wreck. We order a bottle of white.

Midnight Trainwreck just left. She was a hot, drunken mess who chain-smoked, but I — of course — liked her. We made out on the street, then I took her home and she blew me. She blew me on my grandmother’s antique rug. I blew my load in her mouth and she swallowed. She swallowed my load, took a swig of vodka, and left. I assume I’ll never see her again, but, hey, it was a phenomenal blow job. She did that twirl thing with her tongue and used just the right amount of teeth. (Don’t try this at home!) There may or may not have been a finger in the anus. I’m not being coy; I truly don’t know what kind of tricks she had in her bag. Whatever it was, more please. PUH-LEEZE.

1:00 a.m. Trainwreck texts me! “Hey sexy. Mimosas in the morning?”

1:01 a.m. Happyhappyhappyhapppyhappyhappy me.


11:00 a.m. Cafe Cluny with the Trainwreck, who I’m now going to call Tulip. Because, yes, she has the type of first name that generally only overly confident, famously artsy, highly repugnant people can get away with. But she is not highly repugnant. She is a real person with a real story. I won’t reveal too much, but she’s in her late 30s, twice married and divorced, and searching for “stability and soulfulness.” I’ve got both those things and then some!

2:30 p.m. I am giving it to Tulip from behind!!! She is bent over my couch and I’m railing her, as the kids say. She has a great ass. There is a dark beauty mark on it that I find very erotic. The beauty mark is shaped like a state, but I can’t pinpoint which one. I am not sure I’m going to come, but she’s screaming for dear life. I remember from Jayne’s friendly sex tips that I should reach around and rub her clit while fucking her from behind, so I do that. She moves my hands from her pussy to her tits, so that I am holding her (fake?) tits while fucking her from behind. She comes and asks for a break. I take my dick out and take the condom off, and she blows me until I come too. 

6:oo p.m. Tulip is still here. I am allowing her to smoke in my apartment. Is this love?

10:00 p.m. Tulip never leaves. We take separate showers and crawl into my bed, both naked. We have nice, tender sex, and come together after about six minutes. Turns out her tits are fake (I ask). No matter. I feel happy and also terrified. Tulip is a little bit terrifying. She talks a lot about her recent ex-husband. The last thing she says before we fall asleep is, “Ya gotta know when to walk away, right?” This leaves a pit in my stomach for some reason.


7:00 a.m. Tulip has to go home and tend to her dogs. I haven’t heard about any dogs until now. I brush my teeth and walk her to the door. I offer to walk her home and/or get her a coffee for the road. She declines and kisses me on the cheek.

7:00 p.m. Tulip hasn’t returned my text. I wrote her around lunchtime just to check in. Here we go again.

8:00 p.m. I jerk off on my couch to the image of Tulip riding me. In the fantasy, she reaches around and has one finger in my ass.

Midnight I check in one more time with Tulip. This feels appropriate — not needy — considering we had such an intimate second date. Nothing.


10:00 a.m. “Ya gotta know when to walk away.” Well, Tulip knew when to walk away. Because she is totally blowing me off. And so it goes.

6:00 p.m. I buried myself in work all day. I’ll never hear from Tulip again. Not great for my confidence levels, but I do recognize that I probably dodged a bullet. I go on Tinder and start chatting with an Australian girl, Melanie, who works in the restaurant industry. She invites me to say hello at one of the bars she’s involved with. I mess up my hair, throw on some loafers, and head out the door.

9:00 p.m. Melanie is very cute. She is light and spirited. I don’t feel instant chemistry, but look where instant chemistry gets you. Jayne always says, “You never marry your Best Sex Ever.” I could be with Melanie. She’d be fun to cuddle up to. When she pulls up a stool next to me, I notice she smells like a fig tree.

10:00 p.m. She says she has paperwork to tend to, and I take the hint. I’m not sure if we are bored or smitten with each other. I miss Tulip’s cigarette hair and fake tits, but Melanie can have me if she wants me. We say good-bye with an awkward kiss on the cheek. I say, “Let’s try that again.” And we kiss with just a touch of tongue.


9:00 a.m. I may never stop jerking off to Tulip. Jayne bought me a butt plug for Christmas, and I contemplate sticking it up there to experiment with those feelings. But it’s too much work! I do taste my come, though — does anyone else do that? One of the things I’m insecure about is that I might have funky spunk. Tastes fine to me, but I literally have nothing to compare it to.

Noon Melanie and I text some nice, nothing-special messages. We have a date lined up for tomorrow night. I text Jayne for suggestions regarding where to take an Aussie food snob. Jayne says she likes her already and reminds me that Australians seem super-sunny and sweet, but they’re really just raging alcoholics. Oh, goody!


10:30 a.m. I can’t say I’m not haunted by the Tulip disappearance. She was out of my league financially and probably in looks too, but we had a pretty good time — and I thought the sex was hot!

Noon I go down the “I am the world’s worst lover” rabbit hole. I wish I had someone to be upfront with me about this. Part of me thinks sleeping with Jayne would be a solution, because she’d tell me exactly what needs work and possibly reveal to me some hideous habit or stench I have that I am utterly unaware of. But I don’t want to sleep with Jayne, for several reasons — not the least of which is that I am way too scared to know how lousy I look/smell/sound while doing the sex.

8:30 p.m. Melanie walks into the restaurant looking fresh out of a shampoo commercial — but like a CVS shampoo, not a Sally Hershberger shampoo. (Jayne goes to Sally H.)

11:30 p.m. We have a nice meal, but Melanie insists on splitting the check. A bad sign — I think? Or maybe an Aussie thing? I kiss her outside the restaurant in that pre-Uber, post-boozy meal kind of awkward sitch that any single New Yorker knows about. And then Melanie yawns. She literally yawns. She says, “To be continued another night?” Yeah, we’ll see. We will see.

Want to submit a sex diary? Email and tell us a little about yourself.

The Guy Who Doesn’t Know What He’s Doing Wrong