This Week’s Sex Story: A Man Torn Between Sex and Commitment

Photo-Illustration: Marylu Herrera

This week, a fintech executive tries to decides between getting serious with one woman and having wild sex with another: 47, single, New York

DAY ONE

7:12 a.m. Wake up alone. The apartment’s bright. It’s on the second floor of a West Village brownstone. I bought it two decades ago with my first bonus. I make a double-shot latte and stand at the window in my boxers, watching a woman walk a small, serious dog down my charming street.

9:30 a.m. I open my laptop, which I try not to do on Sundays. I scan a thread from our CTO but do my best not to really think about it. I’m a VP at a fintech company, so I’m looped in on everything. I close the laptop in the spirit of having a calm Sunday.

11:45 a.m. Text from Mia. Calm is not the word I’d use to describe her. It says “thinking bout u,” no punctuation. Mia’s a freelance photographer about 20 years younger than me. She’s gorgeous with a gap between her front teeth that makes her look like a French model. (She’s also a French model.) We’ve been on and off for a year. It’s the wildest sex I’ve ever had. Every time we see each other, it’s all night, all positions, dirty talk. She slaps me. She calls me her “cum machine.” It’s nothing like I’ve ever experienced. It keeps me hooked and distracted from more age-appropriate, compatible women.

Mia likes to mess with my head. She’ll write “thinking bout u,” then wait a few days to respond to a text back that reads …

3 p.m. … “Dinner this week?” I know she won’t answer. I’ll hear from her on Wednesday. Put my phone on the coffee table and take a walk.

7:30 p.m. Dinner on Grove Street with my friend Patrick. I have a delicious roast chicken and a glass of Burgundy. Patrick is 52, remarried to someone his age, and always reminds me that he made a very good decision giving up the young ones for a stable relationship with a good woman. At the end of dinner, he says, “You look tired.” I tell him to fuck off.

However, he’s right. I’m tired of dating like I did in my 20s. I got married briefly in my 30s. It was disastrous, but I’ve been “recovering” for long enough. I’d like to settle down. I’m getting too old for games.

10:15 p.m. Natalie calls. Natalie’s 42 and has a great job with an international hotel brand. We met at one of her properties in London. She’s petite — strawberry blonde, green eyes. Mia is kind of harsh, a ’90s-supermodel type. Natalie is beautiful too, but much more low-key. I like Natalie, so I answer. She wants my take on a work conflict. We talk while I walk home. I sit on my stoop to finish the conversation. Per Patrick, I’m tired.

DAY TWO

6:45 a.m. Check my phone. Data issues, security issues, HR issues, blah blah blah. I shower, make coffee, and am on a work call by 7:30, still in a towel, pacing the kitchen.

9 a.m. At the office in Hudson Square. Drinking a second coffee from a cart outside. Back-to-back meetings all morning.

1:30 p.m. Lunch at my desk, a kale Caesar salad that my assistant always gets for both of us. It’s helpful that she’s a lesbian, because there’s zero sexual tension even though I think she’s the most wonderful woman alive and tell her so often.

3 p.m. Voice-note from Natalie. She loves a voice-note. It’s nice hearing her in the middle of the day. I’ve slept with her a handful of times. It’s good sex, and she’s nice company, but the Mia of it all derails me from taking further steps.

Our relationship is pretty stagnant: I give Natalie advice on how to be a grown-up, and twice a month, we get dinner and have sex. I text that I’ll call to unpack the co-worker conflict after work.

6:30 p.m. Walk home, which I do almost every day. Sometimes, like today, I’ll stop at a bar, have a glass of wine, and read on my phone. My version of meditation.

9 p.m. Call Natalie from my stoop. We talk about our relationship. (Friendship?) She calls me “emotionally adjacent.” I tell her I don’t know what that means. She says she loves seeing me, but I’m “out of reach” and she can’t figure out why. I know why … chaos agent Mia. I don’t say that because it feels mean. I tell her I’ll work on it. Not sure I mean it.

DAY THREE

7 a.m. A message from our CTO: a complicated work thing is resolved. It’s the closest thing to joy I’ve felt all week.

12:30 p.m. Take myself to lunch at Ci Siamo to celebrate. It would be nice to have a wife or girlfriend to call about this work saga. I’m close with my siblings and many friends, but I feel empty a lot of the time. It’s okay that I don’t have kids, but I’d like to find my person.

6 p.m. Mia texts, “in the neighborhood.” The West Village version of showing up without warning. She follows, “is that ok?” … technically asking permission, while functionally assuming a “yes.” I write, “come up.” We know the drill.

7:30 p.m. She arrives with wet hair, like she just showered. Odd, because she lives in Williamsburg. The math doesn’t math, but whatever. She smells really good, like cedar. We open the bottle of natural wine she brought and talk about a shoot she has next week in Lisbon. I’m super-aroused just being near her.

9:15 p.m. The sex is extraordinary, as always. Tonight, she wants hours and hours of oral. I’m happy to accommodate. We lie in my bedroom with the city below us and I feel 23 years old. Before I remember that I am not.

11:30 p.m. As she leaves, Mia does this thing where she studies my face for a moment, like she’s trying to remember what I look like in case we never see each other again. I feel good, confused, and slightly like an idiot.

DAY FOUR

7:30 a.m. Pilates at a studio I’ve been going to since my divorce. At first, I went to meet women; now, I go because I think about longevity a lot these days. Pilates makes me feel like someone with his life together.

10 a.m. Meeting with the CEO, whom I went to business school with and really respect. Spend the morning arguing productively in a conference room with him and our head of design. I’m energized.

3 p.m. Natalie wants to go to Via Carota for dinner, a hard reservation even for me. I tell her I’ll try. Then I ask my beloved assistant to try.

6:45 p.m. Score. We got a table. Natalie looks beautiful and has a lot to say about her work drama. I sit across from her asking myself, Should we be just together? She’d go for it if I suggested it. She doesn’t want kids. Her age is reasonable. I’m just afraid to cross that line until I’m sure.

10 p.m. We walk around the city. Why don’t I want to rip her clothes off? Maybe Mia has wrecked me for other women.

11 p.m. But, of course, we end up at my place. We have nice, slow, emotional sex. It’s not bad. We both enjoy ourselves. Unlike Mia, Natalie always wants to stay over. It’s fine with me. I do enjoy her company. As we doze off, we talk about her family in Cincinnati and how she’d love to bring me home sometime. She falls asleep mid-sentence, which is the cutest thing I’ve ever seen.

DAY FIVE

7:45 a.m. Make Natalie a coffee for the road. She leaves wearing one of my flannel shirts over her dress from last night. It makes me feel good.

8:30 a.m. Three-way call with general counsel about a potential partnership. I take it in my boxers in the kitchen.

11:15 a.m. Shit. The first Natalie text arrives at 11:15. Another at 11:22. She says she’s spiraling a little because I was weird when she mentioned her family. She wants to know if she’s reading into it or if I bumped on the idea. I want to write back but have a call, so I say I’ll respond as soon as it’s over. I don’t want to leave her hanging because I know she’s feeling vulnerable.

2 p.m. This is my life … just as I’m about to write Natalie something from the heart, Mia sends a photograph, no caption. I’m aware that Mia’s a big part of this Natalie situation, but I don’t think I have to be honest with Natalie about it. Do I? Instead, I text Natalie that I’d be thrilled to meet her family and apologize if I sounded unenthusiastic. I was just tired from the wine and sex! I’d love to meet them. It’s not a lie. It’s a half-truth because of the messy Mia component.

7 p.m. Get a glass of wine on my walk home. Feeling torn about Natalie, like it’s time to shit or get off the pot. How romantic.

9 p.m. Call Natalie to reassure her I’d love to meet her family. We get into it a little. She uses the word avoidant. I tell her I’m working on it (I don’t say “by figuring out my deal with Mia”). We end on a good note: I like her, and she likes me, and we’re excited to advance our relationship step by step. I dread her asking if I’m sleeping with other people, but she doesn’t — tonight, at least.

DAY SIX