sex diaries

The Lawyer Who Hooks Up With a Guy After a Scarf Show

Photo-Illustration: James Gallagher

This week, a lawyer celebrating her birthday weekend with someone she knew in college: 27, straight, single, Greenport.


7 a.m. Ugh. Another conference. I’m so over waking up for this shit. I’m an associate at a law firm where I spend a lot of time drafting contracts and researching intellectual property law (with a focus on fashion law). I’m originally from Malta but have lived in the New York area since college. Tonight is going to be yet another evening where we get blackout drunk under the guise of networking.

7:15 a.m. Getting ready, and can’t stop thinking about my ex, even though it’s been six months and I should most definitely be over him. We were together for a year but we broke up and got back together countless times (my friends say seven, I think it’s six), and we speak from time to time. I’m still enjoying the perks of being single, though.

8:30 a.m. Get to the conference. There’s literally a 50-person-strong queue for coffee. Will check in later and remain sans-latte for the time being.

5 p.m. Why did I miss lunch? I’m starving. The lunch queue was equally daunting and the food really didn’t seem worth the time. Why is there literally no one interesting here? I’m hungry for good conversation. Thankfully, there’s networking happening later. How many coffees equal one lunch?

6:30 p.m. Finally, drinks. I’m with this acquaintance — she’s alright. She seems to be into this guy we met over drinks though, and I’m pretty sure she has a boyfriend?

6:45 p.m. I’m scouring the room for anyone interesting. It’s getting pretty late, and I’ve got to be back here tomorrow morning.

8 p.m. A few gin and tonics later and I’m all like, “Tinder, what a great idea!” A couple of swipes in and this super-tall guy catches my eye. We match. He comes on strong with a “Where are you?” and we meet at the bar. He’s cute!

Midnight Said bar starts to close and politely kicks us out — it’s getting pretty late and the four of us (my acquaintance, the guy she’s eyeing, this Tinder match, and myself) decide to look for a place that’s still serving drinks. The Tinder guy is a very standard gaming bro, good-looking, has money, and seems like he’s into me being aware of these qualities.

4 a.m. It being a weeknight, finding anywhere that served alcohol at this hour was no easy feat. That being said, I’m not a quitter. We found a strip club that was still open, got some drinks, and made out on a ratty sofa. Now I’m home, ready to pass out.

7 a.m. Fuck. I’ve slept for a little over an hour. Back to the conference. I can’t believe I have to smile for the next nine hours.

1 p.m. This conference is full of pseudo-intelligent men. I’m so bored. Today feels like four days rolled into one. I can hear the seconds passing on my watch.

4 p.m. I swear, I’m never drinking on a work night again. I’m going straight home — fuck networking drinks and fuck all these people who can drink for three days straight and still be valid people throughout! I am not one of them. I shall go straight home, make poached eggs on toast, and get right into bed.

7 p.m. There are no eggs in my fridge.

10:33 p.m. The batteries ran out on my vibrator. Today couldn’t get any worse.


9 a.m. Today’s my 27th birthday and I’ve got drinks planned with friends so that’s something to look forward to all day.

1 p.m. Chatting on my phone with this guy I know from college. He’s smart and alright-looking, just not “in your face” hot. We weren’t really friends back then, but we ran into each other a while ago and got to talking via Instagram. We’ve had some back and forth and he might make an appearance tonight.

4 p.m. Finally, home from the conference. Will have a nap and get ready and actually be on time to my own birthday drinks. I’ve planned an outfit and laid it out and set an alarm.

8:45 p.m. No one’s surprised when I’m late to my own birthday drinks. They all know me so well, it’s rather heartwarming if I’m honest.

Midnight Off to a party so we can dance to ’90s classics and pretend we’re still 18. I’m wearing a very distinctive (faux) fur jacket so I’m pretty hard to miss, and this is what I tell the guy from college I’ve been chatting with. He finds me (thank you, faux fur), and we finally make out, but the night starts ending, much to our collective dismay.

2 a.m. Still making out against a wall in a seedy club. The staff really wants us out, so we take the hint and leave. We decided to watch the sunrise with (yet another) bottle of wine — I’ve not slept nearly enough for this much excitement. He’s so smart and funny, too. We decide that we’re not done with each other yet, so we book a hotel room nearby.

3 a.m. We go to our respective houses to quickly pack some clothes and condoms, and reconvene at the room we’d booked. It’s pretty obvious that we’re into each other. As soon as we arrive he throws me down on the bed (so soft and clean, making a mental note to leave a good TripAdvisor review) and starts going down on me.


12 p.m. I’m so hungry and so satisfied and ever so slightly hungover. We had sex twice!  Wow.

7 p.m. We spent the whole day in each other’s company. We had lunch together, we went to the beach, actually went on one of those tourist-trap boat rides around the harbor, went back to the room, had sex again, had a nap, had sex again (in the shower this time), went for dinner, had sex again. It did feel rather real, like it could maybe, possibly be a legitimate thing, you know?

10 a.m. Can we stay here forever? Why do I feel so attached? No more introspective overthinking, back to sleep.

1 p.m. We woke up, had some good conversation and read the news (is this the real life?) in bed, had sex for what feels like the millionth time (I swear, this isn’t a complaint), showered, and went to lunch. This eat/sleep/sex repeat thing is goals.

5:43 p.m. He’s midway through an in-depth analysis of the last three months in Maltese politics (he’s from Europe, originally) when I realize how much I actually like him.

7 p.m. I drove us back home. Back to reality, time to stop pretending we’re a couple.

9 a.m. I sent him a text saying how much I enjoyed our time together and he’s already replied. I can’t believe it.

Now, it’s not that I have low self-esteem — sure, I sometimes need validation and I’m not proud of that, but generally speaking I’m rather confident. It’s just that lately, men have been so consistently disappointing.

10 a.m. Not gonna lie, I also spend a fair chunk of the morning having flashbacks to the weekend. I’m quite sure my colleagues have figured out how I spent my weekend from the look on my face.

1 p.m. I feel like I’m walking on a cloud.

4:30 p.m. He’s taking forever to reply to texts now. Maybe he’s just not that into me. Or maybe he is, I have no idea. He does seem like he works pretty hard, maybe it’s that. Although, people find a way to make time for the things they prioritize, so probably not. Either way, I’m already catching myself trying to justify his behavior because I don’t want to believe he’s at all like most of the other men out there.

8:34 p.m. Just remembered I have an event tomorrow — a friend designs these really lovely silk scarves and she’s throwing a small show with drinks after. Must plan my outfit.

Midnight Remember that I actually bought new batteries for my vibrator! Satisfying session, then sleep.


1 p.m. I touch base with my family back home. My parents divorced when I was 6. I had a religious upbringing, but in more of a societal way, not really enforced by my parents — so I was free to do my own thing. I’ve been an atheist since I was about 12.

6 p.m. Work passed very quickly today. I think everyone just wanted to get the day over with. I need to get home, get ready, and be punctual. I decided to wear a white coat that I bought last year and have spent more on dry cleaning than the original price of the coat, a black mesh T-shirt tucked into wide-leg black velvet pants, and a fluorescent box clutch.

8 p.m. My best friend is joining me tonight for the scarf show. I was supposed to pick him up 15 minutes ago …

8:17 p.m. Finally pick him up. We get to dissecting the conversations I’ve had with last weekend’s fling. We conclude that he’s not into me and that I should move on. Fair. We make it to the show on time, for once.

10:20 p.m. Shots and binge-drinking seem to be the Tupperware parties of our generation. The show was a museum and was super fun — everyone there looked really good and there was just kind of a general good-vibes feeling where everyone seemed to be enjoying themselves.

A guy my friend’s hooked up with before — my best friend’s gay — is here, with a friend of his own. The friend is pretty cute and straight (the grapevine has informed), albeit a little short, but it’s fine, he seems really nice. He has this familiar safety to him … it’s quite odd but in a charming way.

12 a.m. He actually asked my best friend if he thinks it’s okay if he dances with me. What is this? 1921? I love it.

2:45 a.m. The four of us — my best friend, the guy he’s been with before, that guy’s friend, and myself — all go back to the friend’s place to continue the party, i.e., separate into two bedrooms in order to get with our chosen people.

He tells me how it’s been forever since he had sex, how he went through a bad breakup two years ago and since that ended he’s sort of lost confidence with women. He seems incredibly honest and genuine. We talk for a long time, and he’s looking at me as though I’m a combination of all of his most intimate fantasies come true.

He doesn’t have a condom, though, and neither do I. The night ends with naked exploration, good conversation, and no sex. I wonder if this one will actually call me like he says he will?

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

The Lawyer Who Hooks Up With a Guy After a Scarf Show