sex diaries

The Playwright Who Wishes She Could Sleep Around Right Now

Photo-Illustration: James Gallagher

This week, a woman doing everything she can to resist texting her ex-boyfriend: 42, single, Brooklyn. 


10:30 a.m. After running some errands I look at my phone. No messages. My ex texted me “Good morning Beautiful” for the last two years of my life. But not anymore. We are over. It hurts so bad. We broke up in June when I finally accepted that he was never going to marry me or start a family with me. He is completely opposed to marriage and doesn’t want kids. I can’t sacrifice either of those things even if it means being with the man I love. We’ve been over for three months and I can’t stop thinking about him.

2 p.m. I try to work on my script. I’m trying to write a play. It’s about heartbreak. I began writing it about a year ago, actually — I always knew this relationship had an expiration date. I’m a copywriter for various brands so that’s how I make actual money.

9 p.m. Drinking wine and trying to numb my feelings with bad TV — 90 Day Fiancé.

11:30 p.m. Can’t sleep. Hope I did the right thing leaving him.


6 a.m. I barely slept. My mind wrestles with itself all night long. I can’t put into words how hard it is not to text him. It’s brutal. What would happen if I did text him? We’d go right back to our old ways — passion and hot sex — only to know it was ephemeral. I had to put a final ending to it at some point or this would go on forever and I’d never get the life I wanted.

1:30 p.m. My best friend and I go on a walk. She knows I’m struggling. We agree that the heartbreak is lingering longer than it would have because life is at such a standstill. It’s not like I can go out and find someone new. I’m so stuck in the heartbreak — there’s literally nowhere to go to escape it.

6 p.m. I always said if things didn’t work out with him, I’d give up on men. I’m not sure it’s so easy, but I’m going to try and date both men and women moving forward. I have no idea if it will feel wrong to date a woman, or right, or like there’s no difference at all. It’s something I have to explore and experiment with.

8 p.m. I join a few queer dating apps. The problem is that I feel timid about putting my real photo on my profile. I decide to put a pause on the profile-making and go to sleep.


8 a.m. I’m from Georgia, so I spend the morning making a last push trying to flip the few Republican friends and family I have down there. It’s tricky — I try not to push too hard or too soft. Leave a few more Facebook comments before starting work.

5 p.m. I notice a cute guy in front of me (six feet away) at the burrito place where I’m picking up dinner. He’s very fit. If there weren’t a pandemic I would try to flirt and maybe even allude to some casual sex. I actually think that fucking someone new would help me move on from my ex — but that is impossible right now. I would never be so irresponsible.

9 p.m. Take out my very chic vibrator that I bought myself for Christmas and try to get off. I have no one to think of, no one who I can fantasize about. So I get out my computer and surf porn, which I’m new to. I know there’s new stuff that I’m not tapped into, so I watch kind of cheesy and gross porn because it’s the only stuff I can find.


9 a.m. I walk two miles to a coffee shop I really like. On the way, I try to find a good podcast. I can’t, so I call a friend. This is one of my tricks — always call a friend and talk for as long as possible so the phone is unavailable to text my boyfriend. We talk about her pregnancy, which slightly depresses me but it’s not her fault. I am 42. I might be okay since my eggs are frozen — which I decided to do about five years ago when it became clear I’d need more time to figure out motherhood and partnership — but things are looking bleak. I can’t bear to think about it.

3 p.m. Go to Sahadi’s to buy some ingredients for a lamb stew I’m trying to make. My ex and I were amazing cooks together. It was a huge part of our relationship. I cannot imagine making this dish and not at least sending a picture of it to him. But I also don’t want to not make it just because I can’t trust myself.

7:30 p.m. The lamb stew is delicious and so is the Rioja wine I paired with it. I eat alone while watching the news.


10 a.m. I spend the morning on two Zoom calls about copywriting projects I’m working on. After a while I turn to researching the best lo mein in my area, which I spend way too much time doing.

1:30 p.m. As I look through relatives reactions to the news on Facebook, I think about how grateful I am that my ex isn’t on social media. I couldn’t handle seeing him on here every day. It would destroy me.

9 p.m. Once again, I am going nuts wondering if I did the right thing. About a year ago, I accepted that I could not change his mind about marriage and kids. But I thought maybe I could change mine. Wasn’t he enough? This is the question that tortures my brain. It’s the line he always used on me. “I should be enough for you. I promise to be enough for you.” Am I so old-fashioned that I need something so un-modern as marriage and kids? It makes me feel ashamed. But I really do want those things. My mind goes back and forth as I move my body around in bed, unable to get comfortable.


9 a.m. In the shower this morning, I noticed a few gray pubic hairs. I’m pretty much okay with them but it’s crazy to think that I’m in my 40s; half my life is over. I’m a childless middle-aged woman. How did that happen?

11 a.m. I spend a few hours trying to figure out if my new insurance covers therapy, and then which therapists accept my insurance. I should have done this earlier, but I hate dealing with insurance. I dread it like the plague. I’m not stupid … I know this relationship is a symbol of something else in my life that isn’t quite right, something internally. I just don’t know what yet. I have not, as they say, done the work.

10 p.m. Tomorrow is my ex’s 42nd birthday. I really want to send him a note. Part of me thinks I’m ready to communicate with him and that I can handle it without going “all in.” But I know that’s a delusion. It just seems really mean not to wish him a happy birthday. I decide to figure it out in the morning.


9 a.m. I decide to text him: “Hey you. Happy Birthday. Sending love. No need to write back.” An hour later he does write back. He’s happy to hear from me. He starts asking questions about my life and my script. I send him a picture of the lamb. We both feel alive talking to each other again, even just for his birthday.

4 p.m. I haven’t really done anything today except lay around the house and text. He tells me he misses me and hasn’t met anyone else, not just because of COVID, but because “no one is you.” He’s not one to bullshit, so I believe him. I’m so confused. I know I need to end the texting right now, but it’s the first time my heart has felt whole in months.

11 p.m. We text a lot today, and I feel like I’ve been in an unproductive haze. It’s like a high. I’m stoned on being back in touch and as it always goes, my life becomes dysfunctional as a result. He said he would love to see me and talk over a coffee soon. I told him I’d think about it. I am never going to sleep tonight, or ever again.

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The Playwright Who Wishes She Could Sleep Around Right Now