In this week’s sex diary, a man struggles with insomnia, uses five different dating apps, and texts his ex-wife: 38, single, New York.
DAY ONE
10:30 a.m. Roll out of bed, annoyed to be waking up so late. I finally got to sleep at four in the morning. Ugh. I’ve been a night owl my whole life, and it’s still the weekend, but this is getting ridiculous.
To be fair, I’ve got some stuff going on: I got divorced a year ago and I’m still adjusting to the single life. I was with my ex for ten years, and we were married for eight. Nothing crazy happened; we just grew apart and changed as people. I was a very different person when we first met — I had zero self-confidence, and I think she knew that. She didn’t treat me super well at times. The divorce was mostly amicable and we’re still good friends, but it’s weird living alone.
1 p.m. Being lazy feels good, but I need to get moving a bit. I take a long, meandering walk and get some groceries. Then I kill an hour on the dating apps — I’m using five right now. They take up a ton of time, but it’s my first time using them and it’s pretty damn fun.
3 p.m. Call my mom to see how she’s doing. She has dementia and had to go into a care facility last year. She’s in good spirits today, and it’s nice to hear her laugh.
4 p.m. Respond to some app messages. I’m up-front with the women: I’m not looking for anything serious right now, given my mom’s situation and the fact that I’m pretty recently divorced. They seem to respect the honesty.
6 p.m. Rachel, a Hinge match, texts me. She invites me to visit her in Long Island, where she lives. She’s 49, divorced, and gorgeous. We met up in the city last week. She was staying in a hotel and after grabbing a quick drink at the bar, we went straight upstairs. We had sex four times and parted ways the next day. I tell her I’m down to come see her ASAP.
9 p.m. Mom calls again. She says her laptop isn’t working. I’m able to coach her through plugging the charger back in, and all is well.
9:15 p.m. I call my brother to commiserate about Mom. He lives nearby and we’re close. We also split the cost of her care, which makes things easier, but it’s still really expensive.
11 p.m. I should really try and sleep. I read for a while before masturbating to the memory of my time in the hotel with Rachel.
DAY TWO
10 a.m. Morning! I slept too late again. Today is a workday. I’m a freelancer; I do copywriting for design-focused clients. I work from home and I have a couple of contract gigs going at all times. Right now, I’m working on revamping a brand’s website so the copy is more witty and engaging. My supervisor is an older gay man. We’re friends, and he loves to hear me dish about my sex life.
1 p.m. Emilia messages me about meeting up on Friday. She’s a British woman I met on Bumble. We got coffee last weekend. We had a great time, and I’m a sucker for accents, but I’ve already booked another date for Friday.
3 p.m. Speak of the devil. This Friday’s date, Miranda (also from Bumble), texts me to confirm. She says she’s excited and we text back and forth for a while. The texts start to turn a little horny and I decide to hit the gym before I get stuck at home sexting all afternoon.
4 p.m. Gym is packed. I get into it with a guy who’s been on a machine for over 15 minutes, scrolling his phone. I feel bad about the confrontation, but he was annoying me. Ugh. Maybe I just wanted to get into a fight?
7 p.m. Try to tackle some of the work I missed when I was sleeping in and messaging with women.
11 p.m. In bed, reading, hoping to drift off soon.
DAY THREE
9 a.m. Feel slightly better rested this morning.
2 p.m. At work. I have a couple of production meetings, help a client with some SEO things, and do some reading — I have to keep abreast of design trends. It’s all pretty easy and I feel like I should be getting more done, but sometimes there just isn’t a ton to do. I get paid either way, so a laid-back day is just fine with me.
3 p.m. I spend some time responding to women on the apps.
5 p.m. Mom calls. She sounds sad, so I do my best to cheer her up. I’d give anything to make her feel happy.
6 p.m. My brother and I hit a workout class. I can barely breathe, but feel better afterwards. We walk around and talk for a while before heading home. I’m glad to have him nearby.
9 p.m. My ex-wife calls. We talk on the phone every so often. She tells me she was just promoted at work. I’m genuinely happy for her, and in this moment, I really do miss her.
11 p.m. Rachel sends me a voice memo of her masturbating. She then calls me just as she’s coming. I think my trip to Long Island is going to be a lot of fun …
DAY FOUR
10 a.m. Get out of bed after an hour or so of sending app messages and reading. Maybe I should just accept that I’m not a morning person.
11 a.m. Hit the gym. I practically have the place to myself for back and biceps day.
1 p.m. Productive workday so far. I call Mom and see how she’s doing. She sounds uncertain, and five minutes into the call asks me to clarify who she’s speaking with. I’m crushed.
3 p.m. Restless and agitated. I feel like I need to get out of the house tonight. I text Emilia and ask what she’s up to. We make plans to meet at a bar in Brooklyn, which is cool because I can go and see my brother after. He lives nearby.
7 p.m. At the bar and Emilia arrives, looking amazing in a low-cut top. We grab drinks and snag a table in a corner. She keeps bumping me with her feet, and it doesn’t feel accidental.
8 p.m. The bar is quiet and romantic. We’re just talking and drinking when she tells me she loves the sound of my voice. Women always say this. I don’t really get it, but I definitely don’t mind it. She then pulls a book out of her tote and asks me to read to her. We’re both lit nerds and she’s quirky, so I roll with it. I read to her for a bit, and after a few pages, she kisses me. We pay our bill, head out, and make out for a while outside of the bar.
9 p.m. After parting ways with Emilia, I head to my brother’s place. We have a drink and talk about Mom’s situation and the financial realities of her care. On my way out, Emilia texts me: Would you want to come over? She sends her address.
10 p.m. At Emilia’s. We go to her room immediately and proceed to have great sex. She’s passionate and loud. She has roommates, and at one point she makes me cover her mouth. It’s incredibly hot. She wants me to stay over, but I have enough trouble sleeping already. I also don’t want to give her the impression that this is more serious than it is.
11:30 p.m. Back at home in bed. My mind is rattling. Maybe I need to start meditating?
DAY FIVE
9 a.m. Tired and definitely didn’t sleep much.
12 p.m. Texting with my ex-wife. We’re just sending each other memes. We never talk about dating stuff.
3 p.m. Grind at work for a while, then catch my supervisor up on my date with Emilia.
4:30 p.m. Walk over to the library after and get a book I placed on hold. On the way back, I give Mom a call. She remembers who I am and I make her laugh with my Ed Sullivan impression. She always loves that one.
11 p.m. In bed about to drift off when Miranda messages me. It soon turns into sexting. I’m not big on sexting, especially Miranda’s version — she kind of just waits for me to write her sexy things, without responding with much of anything.
11:30 p.m. Well, I came, and now I’m more awake than ever. I start my new book and try to relax.
DAY SIX
8 a.m. Woke up an hour before the alarm. Not bad, but I think I need a vacation. I haven’t taken one in years.
3 p.m. Make my way through the workday. I’ll be honest, most of it is swiping on the apps.
5 p.m. Gym for leg day. It’s crowded, but my luck is good — I get to every spot I need.
8 p.m. Meet Miranda for our date at a bar downtown. She’s a good conversationalist: tells interesting stories and asks me a lot of questions. She’s also stunning.
10 p.m. Walking Miranda home. We make out in front of her place. She says she’d like to see me again, and the feeling is mutual.
10:30 p.m. Home. I get a text from Melissa, a 50-something surgeon who lives in New Jersey. We matched a month ago. She seems like an oddball, which I like, and is very up-front about her sexual desires. Tonight she jokes about her stamina and says she could be in New York in less than an hour. I tell her I’ll be waiting, not entirely sure if she’s joking.
DAY SEVEN
11 a.m. Wow, another late morning. Today I’m headed to Rachel’s place in Long Island. I text her that I got a late start and I’ll be there in a few hours. Frankly, I feel like canceling, but I’d feel shitty backing out this late in the game.
12 p.m. On the train. My brother texts me and asks if I’m still alive. We make plans to get together tomorrow, but only after I’ve slept as long as I feel like it.
2 p.m. Arrive at Rachel’s condo. It’s nice and enormous. We sit and talk for a while before she asks to go to the bedroom. I give her a long massage, and I can tell how much she loves the attention. I feel exhausted, but she looks so good that I’m still horny. We have sex and shower together afterwards.
4 p.m. We hit a restaurant. The conversation is nice, but I feel bad because all I can think about is going home to sleep.
6 p.m. Back at the condo. We start to have sex again, but I’m too tired. I eat her out instead. Afterwards, she wants me to stay over, but I tell her I’ve got tons of work to catch up on from the past week. She seems disappointed.
7 p.m. She drives me to the train station. I can see notifications from Emilia and Miranda on my phone.
7:30 p.m. On the train home. Maybe I’ll even go to bed early tonight.
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Alyssa Shelasky , 2024-02-10 00:00:30
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