The Personal Assistant Who Meets a Woman at Trivia Night

In this week’s story, a woman who’s traveling for work finds the right place to meet queer women: 34, single, New York.  

DAY ONE

8:10 a.m. I drag my ass out of bed. It makes no sense that I’m this exhausted given I went to bed so early last night. Mental note to get my blood work checked — am I dying? Why am I always so lethargic? I’m only 34!

10:45 a.m. My first task of the day starts now. I’m a personal assistant. My boss is a TV personality. He’s gay and very nice. Every day is a new adventure. Right now, I’m tasked with picking up a catering delivery and bringing it to his apartment to help set up a lunch meeting he has there.

1 p.m. My boss invited me to join the lunch meeting. It’s with a producer who he often collaborates with, but they wanted to have the meeting in the privacy of my boss’s apartment since they’re discussing another reality star who’s been in the news recently and they want to be discreet. He always includes me in these conversations. I’ve been with him for almost ten years — sometimes we feel more like business partners than anything else. We’re both single and queer, so we talk about our love lives all the time too.

4 p.m. I have to return three huge duffel bags of clothes to the RealReal. I have no idea if my boss wore any of them, or why he had all these outfits. I just have to get it done. Standing in line there, I remind myself to ask for a raise. My fucking back is breaking!

6:30 p.m. Drinks with my friends. Most of us know each other from the theater world. We’re all striving actors, including myself, although it’s been at least a year since I auditioned for anything.

9 p.m. I grab two slices of pizza and head home. I’m on a break from the dating apps, so my nights are quieter than ever. I used to scroll for hours upon hours. I’m trying to adjust to the nothingness of life without the apps, but the break is good — I really think I was addicted to them.

10 p.m. I’m too lazy to go get my vibrator, so I masturbate the simple way, with two fingers and my imagination. I think about the salesgirl at the RealReal today. She was pretty, kind of goth, kind of bitchy. I should have asked her out, but honestly, I just wanted to get the fuck out of there.

DAY TWO

7 a.m. My boss meets with his trainer on Tuesday, so I usually stick around and help go through his emails and scheduling and other loose ends while he works out. So today, I’m sitting in the corner of the gym (in my boss’s apartment building), going through everything, interrupting his session with this and that. It’s a good way for everyone to multitask.

10:45 a.m. We’re at my boss’s kitchen table going through his production schedule for the upcoming year. He looks at his phone and tells me he just got a text from a guy he’s been seeing. I know that this new guy is a dirty dog. A few years ago, he started dating one of my college friends, and he was not very nice to him; he would disappear for weeks at a time, that kind of thing. I’ve warned my boss but try not to get too involved. We already have some issues with boundaries (in that we don’t really have any), and I don’t want to overstep.

2 p.m. We have a working lunch together in Soho. The waitress is hot, and my boss awkwardly asks her if she’d go on a date with me. She says she’s straight and has a boyfriend. Awkward!

5 p.m. I text Gia, a girl I’ve been casually seeing. We met through work, at an event my boss brought me to. I have a fun work event tomorrow and need a date. She’s interested but has to move a few things around. She’s a stylist and is always traveling and working, but that’s not the real issue for us. The real issue is that Gia isn’t out to her very big, very Italian family. At first, there was something sexy about that. But it turned kind of icky when I innocently posted the two of us at a charity event and she asked me to take the post down. That just felt weird. She’s from a religious family, so I respect it, but it just feels wrong to be with someone who still has a conflicted relationship with gay people. Regardless, she’s gorgeous, and the three times we’ve had sex were insane, so I’d love to see her tomorrow.

8 p.m. My boss and I are at a documentary-film screening. It’s hard not to fall asleep. Again, I’m always lethargic!

10 p.m. My boss is hamming it up at the after-party and I’m in an Uber home to bed.

DAY THREE

9 a.m. Wake up exhausted. WTF. This time I really do schedule some blood work. They say I can come in tomorrow morning, but I have to fast the night before, and I plan on having fun tonight — so no thank you. I make an appointment for next week.

11:30 a.m. I spent a few hours editing my boss’s next book. I’m proofreading, giving notes, giving feedback. He’s a decent writer, so it’s not a hard lift.

2 p.m. Gia says she can make the event tonight. It’s a fundraiser for a charity that my boss is involved with. Her text reminds me that I have to pick up my dress from the dry cleaner. I was supposed to get it weeks ago; I hope they didn’t get rid of it. Thinking about the dress reminds me of the first night I wore it. I went to a friend’s birthday party and ended up leaving with this drunk couple from Connecticut who were randomly at the restaurant. They were, like, very fancy people who were secretly swingers. They came over to me and asked if I wanted to come home with them. I did not want to Uber to fucking Connecticut, but I was definitely drunk and feeling adventurous, so the husband got us a room at a hotel. I ended up going down on his wife while he watched. I’ve had threesomes before, but this one was right out of a bad porno. It honestly gave me the ick the moment I sobered up, but it made for a good only–in–New York story.

6:30 p.m. Gia meets me in the front of the venue. She looks incredible; always the best-dressed woman in the room. I kiss her on the cheek hello. Gia likes me, but the last time we hung out, I told her I wasn’t comfortable with keeping our fling a secret. She understood what I was saying. I’d love to not talk about any of it tonight and just have a good time. We start with drinks at the open bar.

9 p.m. The event had a lot of speeches, and it was a major turn-on having Gia touch my thigh while the people spoke. My boss was at another table, so I could really relax and just enjoy the night with her.

10 p.m. We’re back at my apartment, hooking up. I’m so attracted to her. I love her body and the way she smells. It’s like cotton candy, but not in the way that gives you a headache. She sleeps over and we hold each other for most of the night.

DAY FOUR

8 a.m. I leave Gia sleeping in my bed to run to a photo shoot for my boss. I need to pick up coffee and bagels along the way. He also texts me to get some “headache medicine,” which means he probably scored as big as I did last night.

10 a.m. The shoot is at a studio in Brooklyn. It’s cool. The stylist on set knows Gia, so we take a selfie and I send it to the sleeping beauty. I tell the stylist that Gia is currently in my bed, and we have a little naughty laugh. The minute I say it, I wonder if I’ve violated some privacy thing. It’s so weird and unsettling being with someone who hides their personal life the way she does.

12 p.m. Luckily, Gia hearts the selfie and it doesn’t turn into a thing.

2 p.m. It’s a long day. Surprise, surprise, I’m tired. I order iced lattes for everyone at the shoot. I love spending my boss’s money. He is extremely generous, so it’s fine. Once again, however, I remind myself it’s time to ask for a raise.

6 p.m. Everyone from the shoot goes out for a bottle of Champagne. Someone asks if I plan to be a personal assistant forever. It’s hard for me to answer that. I really love my job, but I realize it’s not the most ambitious career. I always wanted to act, but it’s impossible to get good roles. And I’m getting older. The truth is, I’m still not sure what to do with my life. I answer the question by saying I love what I do, and I’m compensated well (truth, kinda), and that’s all I know for now.

10 p.m. I’m texting with Gia about the fun we had last night. She’s home in her own bed now. We are flirting and sending selfies and laughing. I’m afraid to ask her if she’s had more talks with her family about her sexuality. I’m too tired to really broach the subject right now anyway. Or maybe I don’t want to know the answer because it will ruin my afterglow from last night.

DAY FIVE 

9 a.m. In an Uber to La Guardia. My boss has an event in L.A., and I’m going with him. I love going there. It’s always very fabulous, and the queer women in L.A. are abundant and sexy as fuck.

1 p.m. On the plane, I try to read the new Tinx novel, but I can’t keep my eyes open. Motion always puts me right to sleep.

3 p.m. We’re checking into the hotel. I see a random TV star who my mother always crushed on when I was younger. I text my mom that I’m standing next to him at reception. She FaceTimes me immediately. If my boss weren’t there, I’d ask the actor to say hello to my mom, but that’s too inappropriate right now, even for me.

6 p.m. I’m on my own tonight. Without the dating apps — which I’m still abstaining from — it’s hard to figure out how to meet someone. I decide to go to a bar I like in Silver Lake and just see what happens.

7 p.m. Sitting at the bar and it’s all straight people, plus no one is talking to me.

9 p.m. Back at my hotel room with room service.

DAY SIX

8 a.m. Big breakfast meeting in my boss’s hotel suite. His entire L.A. team is here. It’s a nice crew. They’re all really good to me. Then again, I’m the one who takes everyone’s breakfast orders, manages the scheduling, and makes sure everything is set up.

1:45 p.m. We move to another hotel, where there’s another meeting with some studio executives. There’s a new executive, Kate, who looks queer and is talking to me more than she needs to. I ask her where I should go tonight, and she invites me to a trivia night she’s attending. So L.A.! It feels like I’ve hit the lottery with this invite, however, so I get all the info and feel excited.

4 p.m. Quick nap in my hotel room.

5 p.m. My boss texts that he kinda wants to come to the trivia night, but I politely tell him that it’s girls only. I’m not sure of this fact, but I really don’t want him to come, and I think he understands what I’m saying.

6 p.m. Another long and expensive Uber to Silver Lake (on my boss’s dime, but still). When I walk into the bar, I know it’s a good crowd for me. Queer L.A. hipsters. I love it. Kate comes over to me and introduces me to her friends. There’s a strikingly beautiful woman named Ivy who catches my eye right away. She’s an actress and crushing it. She’s funny, smart, and grounded. She’s so hot.

9 p.m. Ivy’s girlfriend gets to the bar just as we’re all getting tipsy and starting to talk about our love lives. Damnit. I’m so much cuter than her too! I look around to see who else I’d be into. I don’t want to go there with Kate, because it feels a little too close for comfort.

10:30 p.m. I go back to the hotel without a hookup and feel a little lonely. But I met some good people to reconnect with the next time I’m in town, and I’m here all the time, so that’s going to pay off.

DAY SEVEN

10 a.m. I am not a big Instagram person, but I see that Ivy sent me a DM. She wanted to let me know that she’s in an ENM relationship, and that she thought I was really pretty. Suddenly, I’m like, in love with her.

11 a.m. In the car to the airport, I look at her photos and I like what I see. Shit, when can I see her again? We leave tonight! I tell my boss about the situation. He generously offers to pay for a change in flight, but we’re already on the way to LAX, so that feels extreme. I appreciate the gesture, though.

1 p.m. Just before takeoff, I DM her back that I was so into her last night, and I wish I knew I was allowed to flirt with her. We transition to texting. But the plane is taking off soon.

6 p.m. Back home in my apartment, the texting with Ivy continues. She’s witty and provocative. She’s coming to New York next week for an in-person audition. I jokingly tell her that she can stay at my apartment. She’s like, “Maybe?” Wow. This is on. 

9 p.m. Gia texts about hanging out this week. I almost forgot about her. We make plans for later in the week, but after so much conversation with a proudly queer woman like Ivy, I’m not that into Gia.

11 p.m. I fall asleep after jerking off to thoughts of fucking Ivy. I’m going to tell her that in the morning, too.

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