The Visual Artist Testing Out a New Friend With Benefits

Photo-Illustration: James Gallagher

This week, a woman trying to get over her on-again, off-again lover with a friend with benefits who lives around the block: 27, single, Brooklyn.


9:30 a.m. These days I’ve been waking up later than I like to. I’m a freelance visual artist — I started my own creative studio in January 2020, so yes, I’m currently unemployed.

10 a.m. While I heat my tea kettle on the stove I sit down in my bedroom corner chair and read. I unexpectedly began living by myself back in September after my old roommate decided she wanted a place of her own. I cherish my mornings of peace and quiet after living with roommates for the past decade.

11 a.m. I cross my fingers that my inbox is full of emails from people who want to hire me, but instead it’s filled with LinkedIn recommendations for jobs I’m not qualified for. Financially, it’s not the best time to be living alone for the first time, but after almost a year of living through this pandemic, I’ve given up on the idea that anything goes as planned.

12 p.m. I open Instagram and see a new post from S, a friend of a friend who I’ve recently been flirting with. We’ve been messaging and made plans to get drinks this week, but then I see that he’s escaped New York to travel for work, again. He’s a successful artist, which is hot, but he’s traveling constantly during a pandemic, which is not so hot.

Thankfully over the weekend, K, my neighbor who I’ve had a little crush on for over a year, coyly messaged me, asking if I still live close by, since he heard my old roommate moved. I happily answered yes and we made tentative plans to hang out this week, so I’m playing it by ear. I haven’t seen K since the summer and I’m very intrigued by this flirty rekindling. I’ve always sensed a bit of sexual tension between us.

At the time I was seeing B, a man I met on Tinder and spent early quarantine sexting, which turned into a real-life fling once the COVID rates started declining in June. By September, he told me he loved me and by November he was moving back down South, a blessing from the universe, I thought, until three weeks ago, when he surprisingly came back. I of course had sex with him because what else is there to do these days. It was great, and I will admit that it was nice to be back in his arms after two months. But that was two and a half weeks ago and I haven’t heard from him since, even after he promised to make me dinner. So much for loving me!

2 p.m. I head out to get some film developed in the city and do some grocery shopping at Trader Joe’s while I’m nearby. Going into the city these days is a rare occurrence and I miss TJ’s frozen veggie fried rice.

7 p.m. Even though I just went grocery shopping I don’t know what to make. I settle on a pre-made meal that I bought from TJ’s and put on Sex and the City.

10 p.m. I begin my nightly dishwashing dance party, which usually ends with me dancing in front of my mirror.


10 a.m. Another day stuck at home. I swear I’m trapped in a time loop like Bill Murray.

1:25 p.m. My best guy friend, E, texts me, asking what I’m up to today and if I can come over later to hang. He has to travel back home over the weekend to visit his family. As if this past year hasn’t been hard enough, he’s going through some family issues. I tell him that I’m just doing my laundry and sending emails today, so of course I’ll be there.

4 p.m. Finishing up my laundry. I’m really lucky to have a washer and dryer in the basement of my apartment building.

7:45 p.m. I head over to E’s place. I bring DIY margaritas and chocolate-chip cookies to soothe the pain.

9 p.m. We’re smoking a joint, taking pickleback shots, playing card games, and talking about investing in cannabis stocks with E’s roommate, L. I love hanging with my guy friends, they give the best advice, especially when it comes to making the moves.

10 p.m. After a bit of consultation from the boys, I text K, “Hey! What are you up to this week? I’m free tomorrow.” It’s open but direct, meaning I’d like to get laid ASAP. He responds immediately and plans are confirmed for a bar in our neighborhood for tomorrow night.

12 a.m. I walk home a bit drunk, even though I know I should probably take an Uber. One of the things I miss most is walking home after a great night and blasting music through your headphones.


9:30 a.m. On my way downstairs to pick up a package I spy a dead cockroach on the lobby steps. Gross. Once I get back up to my apartment I immediately text my landlord about it. He tells me he’ll take care of it and proceeds to tell me he’s going on a trip with his family to Aruba on Friday … I’m glad that my overpriced rent is paying for his ethically questionable trip! Wish I could have the same fuck-it energy.

2 p.m. I apply to a few freelance gigs on job sites. While my business is still my first priority, it’s not paying rent at the moment. I’ve had a few interviews here and there, but nothing has pulled through yet. Crossing my fingers.

7 p.m. I arrive at the bar before K and secure a table out back, unfortunately not under a heat lamp. He comes out a few minutes later and takes off his mask. Cute and quirky just as I remember. I really enjoy spending time with him, he’s funny and we’re the same type of person who needs their independence and space. After the usual catch-up banter, he point blank asks how my dating life has been (bold and upfront!). I tell him a little about B, and he talks about a few flirtations that didn’t really go anywhere.

8:45 p.m. After sitting outside for an hour and a half in the freezing cold, I ask K if he wants to get drinks to-go and head back to my apartment. He happily agrees. We get tall boys and watch old music videos on my projector. Five music videos too many later, he finally turns to me and we start making out.

We head to the bedroom and proceed to have rough sex, which I was not expecting but am very into. K surprises me. At face value he’s a tall, lanky, nerdy man (just my type), but in bed he’s a dominant partner. A bit of choking and muffling, ’cause yes, I am loud. While I can’t help but compare him to B, he’s a great and much-needed palate cleanser. Afterward while we’re lying in bed we mutually agree that we’re not looking for anything serious. Just a fun time. I’m into the idea of a friends-with-benefits neighbor.


10 a.m. I wake up to a text from my old roommate who introduced me to K, wanting to hear about our date last night. I take too long to respond and she calls me. I give her the play-by-play. She’s in disbelief, as am I. We laugh and gossip for an hour.

12:30 a.m. I send out a juicy email to my three best girlfriends, retelling last night’s events. Since we can’t gossip at our favorite bar, we’ve been writing each other dramatically detailed emails of our quarantine sexcapades so we can all live vicariously through one another.

4 p.m. I get a bit of work done, but I’m still in a sex haze. I’m mostly just proud of myself for hooking up with a crush.

9:30 p.m. Nightly dance party begins. Early-2000s R&B, specifically the Step Up soundtrack.


12 p.m. I head out to get some photos printed at my local photo shop. I’ve been trying to print out more memories so that when I’m older I can show my kids what this crazy time was like.

4 p.m. My buzzer rings and I run down to see that my mom has sent me a package of my favorite gummy heart candy. I FaceTime her to say thank you and gulp down a quarter of the bag. They’re super sugary and stick to your teeth.

6:30 p.m. I order penne alla vodka with shrimp from my neighborhood Italian joint for dinner. I watch the final installment of To All the Boys on Netflix. Yes, I’m 27 years old and the most exciting Friday night I’ve had in ages is watching a teen rom-com with Italian food and candy from my mom.

9:30 p.m. I post a picture of my very vibe-y Friday night setup, excluding the teen rom-com, on my Instagram Story. K “reacts” to it with the 100 emoji. Reacts on Instagram in my opinion are lame, but I know it’s him attempting to flirt since he left my place less than 48 hours ago.


10 a.m. It’s one of my best friend’s birthdays. My group of friends are all really sad we can’t be together because of COVID.

12 p.m. I finally get her on a call and talk for hours. Being away from your best friends really sucks. Zoom just doesn’t cut it.

3 p.m. I had plans to walk around Chelsea to see the galleries after the birthday call, but it feels as if half the day is already gone.

4 p.m. I end up making my way to the art store instead to get paint for a project. I also get model magic cause why the fuck not! Art is therapy.

7:45 p.m. Scrolling through Instagram I see that K has posted a cute selfie. I mull over whether I should respond and consult with a friend about what to do. I end up sending a casual yet flirty message. He responds immediately with a double text, saying he had a good time the other night. I feel satisfied.


10 a.m. I spend the morning cleaning my apartment. A typical Sunday.  Feeling slightly optimistic about the week to come.

3:30 p.m. Tonight I’m going over to my friend M’s house for a nice dinner. I pick up wine and a treat for her dog who we’ve dubbed my niece. I became a dog aunt over quarantine and it’s the best thing that’s happened to me besides my sometimes sex life.

5 p.m. I arrive at M’s house. It’s just me, M, her two roommates and their two dogs. We drink wine and eat homemade gnocchi and Funfetti cake. We gossip about our latest flings and M’s roommate realizes she knows K from college. Small world.

9 p.m. In a food coma and the wine is putting me to sleep. I’m cuddling on the couch with my niece dog. She’s the best spooner, hands down beats every man I’ve ever slept with.

10 p.m. I come home to an email about a little bit of work for my business. The best thing to end a weekend with! I get all the project details in line. Feeling excited, inspired, and productive. The opportunity to work creatively is a saving grace these days.

11 p.m. Feeling a bit horny, I send K a flirty text.

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