sex diaries

This Week’s Sex Diary: The Assistant Who Sleeps With a Guy in a Santa Costume

Photo-Illustration: Marylu Herrera

In this week’s sex diary, a woman who loves to party keeps meeting men who are sober: 24, single, Los Angeles.

DAY ONE

7:30 a.m. I wake up irritated. I didn’t sleep well because I’d been up late talking on the phone with this guy, S, who doesn’t know what he wants. He’s part of my friend group, and six months ago our mutual friends kind of convinced us to date. It was fine at first, but after a while I realized we weren’t really compatible. There wasn’t a strong romantic connection, and the sex wasn’t always great. Early on he said he didn’t want a relationship, so it was more of a situationship, and I was also seeing other people. But last night he called and tried to convince me to be exclusive. I told him no. It’s all so confusing!

9 a.m. I arrive at work and drink poisonous Keurig coffee. I’m an assistant at a big entertainment company in the business and legal department. My daily responsibilities include answering phone calls, scheduling meetings, and inputting contract info into a database. Basically: I sit at a desk all day, bored out of my mind and underutilized.

10 a.m. My favorite co-worker tells me about her weekend as I sift through emails as fast as I can.

11 a.m. S texts me: “Thanks for the talk last night.” He’s so annoying. If he weren’t friends with my friends, I never would have given him a chance. I was never really that attracted to him — he’s just not my type.

4 p.m. I open up Hinge and angle my phone to try to hide the screen. I would die of embarrassment if any of my co-workers caught me on dating apps. I match with a dreamy blond guy who has the same star sign as me, Aquarius.

7 p.m. We’ve been chatting back and forth for hours. His name is Alex and he’s cute and funny, and we have a lot in common. I still haven’t responded to S. I don’t think I will.

10 p.m. Early night. Bed.

DAY TWO 

9 a.m. I roll out of bed to start my day. I work remotely on Wednesdays. I usually spend my time writing and imagining a life for myself outside of this boring corporate job.

10 a.m. Another text from S. He just sends a question mark this time. I’m suddenly enraged at my friends for setting me up with him. It’s like they think I’m defective because I’m single.

12 p.m. Alex from Hinge asks if I’d like to go get a drink. I pick a bar where I had my first date with the guy I was seeing before S. I’m not really over him. We only dated for six months, but it was intense: We’d said “I love you” and traveled together. He seemed like the perfect boyfriend, and I was shocked and devastated when he broke up with me completely out of the blue. He blamed his depression and anxiety, but I still don’t really understand what went wrong.

6 p.m. I change into a formfitting outfit to show off my butt and cover my eyelids in silver eye shadow. I really need this date.

8 p.m. Get into an Uber and the driver is wearing a pink bunny suit with long, floppy ears. I can’t make this shit up. It’s like a Donnie Darko situation, and I’m feeling a little nervous. He doesn’t say a word as we drive, and I hold my breath.

8:15 p.m. Made it. Bunny didn’t kill me. Alex is outside of the restaurant and he has a motorcycle, which I wasn’t expecting. That’s kind of cool.

8:20 p.m. We sit at the bar and I ask what he wants to drink, and he tells me he doesn’t drink. When I ask why, he says he just “doesn’t like it.” Why did he suggest we get drinks? He shrugs and says, “I can still sit and have water.” It’s confusing, but he’s really handsome, so I drink a beer and try to enjoy the date.

9:15 p.m. Alex seems extremely uncomfortable. The bar is getting louder and more crowded. I don’t think he likes me very much, but he’s hot and I wouldn’t mind fucking him. I suggest we leave and invite him to my apartment. He agrees right away.

9:20 p.m. He hands me an extra helmet and helps me onto the back of his motorcycle. I’ve never been on a motorcycle before, and I’m both excited and nervous. He secures my legs tightly around him, grabbing my thighs with strong hands. I think to myself, Oh, it is so on.

10:30 p.m. We’re smoking a joint together on my patio. So, he doesn’t drink, but he definitely likes weed and psychedelics. Go figure.

11 p.m. In my living room, Alex suddenly turns to me and sweeps me into a passionate kiss. His lips and tongue are wet and delicious. We move to the bedroom. He is just the right amount of rough and sweet …

DAY THREE 

7:30 a.m. I wake up and Alex is gone — he must have left early this morning. I get out of bed and feel soreness between my legs.

10:35 a.m. At work, in a daze. I keep thinking about Alex and how he called me a good girl as I came. I usually hate that kind of dirty talk, but coming from him, it was electric.

3 p.m. I’m bored at work, so I text Alex. He doesn’t reply. I am instantly crushed. I text my group chat of girlfriends to request a night out. They are down and excited.

7 p.m. Drinking with my friends at a bar, trying to forget about Alex, who is still ghosting me.

10 p.m. With three of my girlfriends. We all stroll into a bar together, giggling. I’m pretty drunk. The bar is packed and my friend buys us shots. They are disgusting and I spit mine out under the bar. Luckily, no one sees.

10:30 p.m. I see a tall guy clad in a super-short Santa dress. I’m confused because it’s March. The guy he’s talking to is also wearing a Santa dress. What is happening? I think it’s funny and also kind of … hot? His legs are exposed, and they are long and sexy. I march right up to him and ask him why the hell he is wearing that costume.

11 p.m. Apparently he’s here for his friend’s birthday, and it’s a “dress only” party. “We all had to wear dresses, and these were the only two we could find on short notice,” he says, motioning to his friend.

11:05 p.m. We start dancing, hard. I’m overheating in my long-sleeve denim jumpsuit and cowboy boots. He’s also sweating in his little felt dress. It’s kind of gross but also feral, and eventually we start kissing. I bet we look ridiculous, making out in our outfits.

11:30 p.m. I order him to buy me a drink. He does, but when I ask him what he’s drinking, he says he doesn’t drink. What the hell! Another sober cutie. Well, I find this one more intriguing — he’s confidently at a bar drinking soda in a teeny-tiny Santa dress.

1 a.m. Santa Claus and I take a Lyft to his apartment. He’s a UCLA law student and lives in grad housing. As soon as we’re inside, I rip off my jumpsuit and he goes down on me with the lights still on. At some point, I realize he’s still wearing the Santa dress. I start giggling and he takes it off and throws on a condom. I have fun, but I don’t have an orgasm. He gets me a Lyft home afterwards.

DAY FOUR

8:30 a.m. My head pounds as I wake up. Regret washes over me as I remember the previous night. Did I really sleep with a stranger in a Santa costume?

9 a.m. I tell my bosses I have food poisoning and fall back asleep.

12:30 p.m. I feel disgusting, so I shower.

7:30 p.m. I eat dinner alone. My friends text and ask if I can go with them to LACMA tomorrow. They say S will be there. Ugh. I still haven’t responded to his multiple follow-up texts. I agree and finally text him back: “Hey, sorry, been busy. I’ll see you at LACMA tomorrow?”

10 p.m. S calls me, but I’m too tired and still feeling hung-over. I ignore his call and go to bed.

DAY FIVE

12 p.m. Sleep in super late. I think I’m getting a cold. It must have been the Santa guy.

1 p.m. I reach LACMA, and S is already there with my other friends. We walk off together and chat a little, and he kisses me. As I pull back, I see my friends snapping a photo of us. Ugh. I’m so pissed. He’s not my boyfriend, I think. I literally fucked someone else the other night. 

4 p.m. After a few hours of vacantly staring at art while my couple friends hold hands and fondle each other, I am annoyed.

6 p.m. We eat dinner at an Ethiopian restaurant. The food is phenomenal, but S and I have a whispered argument near the bathrooms. Again, he says he wants to be exclusive, and I tell him he didn’t put any effort into our relationship, or whatever it was. I leave without saying good-bye.

8 p.m. Meeting up with a different group of friends, one of whom is going through a breakup. We sit at the bar, commiserating about how men are awful. And then we go home.

10 p.m. Bed.

DAY SIX

6 a.m. Wake up with the Sunday Scaries. I feel nauseous from my week of boozing and boning.

11 a.m. I’m feeling a little itchy … down there. I close my eyes and pray. When I sit down to pee, there is something green in my underwear.

2 p.m. At the doctor. She lets me know that I have both bacterial vaginosis and a UTI. I’ve never had either before. Great, just what I neededI am prescribed antibiotics.

6 p.m. Eventually, my shame spiral subsides and I worry I’ve been too mean to S. He likes me, after all.

9 p.m. I call S. He is meek as I speak to him. He is surprised to hear me apologize, saying I shouldn’t have been so harsh with him.

DAY SEVEN

11 a.m. I get a text from S. He wants to have dinner and promises he will come to me.

12 p.m. I agree, though I’m nervous. I’m not ready to have a deep, in-person feelings talk. I am suddenly so scared that someone will be able to smell the fungal episode going on in my pants.

7:30 p.m. S and I meet up at an Italian restaurant I’ve never been to. The meatballs are out of this world.

8 p.m. Over pasta and wine, S says my apology made him like me more, which made me like him even less.

9 p.m. We return to my apartment and I tell him I don’t want to have sex, and I think we’re better as just friends, anyway. (I don’t tell him that I have more than one infection.) We cuddle on my couch and he kisses me softly. Eventually, I push him away and he leaves. He seems sad, and it all feels kind of like a breakup, but I am content. There are plenty of other fish in the sea.

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The Assistant Who Sleeps With a Guy in a Santa Costume