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\n Photo-Illustration: Marylu Herrera\n <\/p>\n
This week, a fintech executive tries to decides between getting serious with one woman and having wild sex with another: 47, single, New York<\/p>\n
DAY ONE<\/strong><\/p>\n 7:12 a.m<\/strong>. Wake up alone. The apartment\u2019s bright. It\u2019s 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.<\/p>\n 9:30 a.m. <\/strong>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\u2019m a VP at a fintech company, so I\u2019m looped in on everything. I close the laptop in the spirit of having a calm Sunday.<\/p>\n 11:45 a.m.<\/strong> Text from Mia. Calm is not the word I\u2019d use to describe her. It says \u201cthinking bout u,\u201d no punctuation. Mia\u2019s a freelance photographer about 20 years younger than me. She\u2019s gorgeous with a gap between her front teeth that makes her look like a French model. (She\u2019s also a French model.) We\u2019ve been on and off for a year. It\u2019s the wildest sex I\u2019ve ever had. Every time we see each other, it\u2019s all night, all positions, dirty talk. She slaps me. She calls me her \u201ccum machine.\u201d It\u2019s nothing like I\u2019ve ever experienced. It keeps me hooked and distracted from more age-appropriate, compatible women.<\/p>\n Mia likes to mess with my head. She\u2019ll write \u201cthinking bout u,\u201d then wait a few days to respond to a text back that reads \u2026<\/p>\n 3 p.m. <\/strong>\u2026 \u201cDinner this week?\u201d I know she won\u2019t answer. I\u2019ll hear from her on Wednesday. Put my phone on the coffee table and take a walk.<\/p>\n 7:30 p.m.<\/strong> 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, \u201cYou look tired.\u201d I tell him to fuck off.<\/p>\n However, he\u2019s right. I\u2019m tired of dating like I did in my 20s. I got married briefly in my 30s. It was disastrous, but I\u2019ve been \u201crecovering\u201d for long enough. I\u2019d like to settle down. I\u2019m getting too old for games.<\/p>\n 10:15 p.m. <\/strong>Natalie calls. Natalie\u2019s 42 and has a great job with an international hotel brand. We met at one of her properties in London. She\u2019s petite \u2014 strawberry blonde, green eyes. Mia is kind of harsh, a \u201990s-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\u2019m tired.<\/p>\n DAY TWO<\/strong><\/p>\n 6:45 a.m. <\/strong>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.<\/p>\n 9 a.m.<\/strong> At the office in Hudson Square. Drinking a second coffee from a cart outside. Back-to-back meetings all morning.<\/p>\n 1:30 p.m. <\/strong>Lunch at my desk, a kale Caesar salad that my assistant always gets for both of us. It\u2019s helpful that she\u2019s a lesbian, because there\u2019s zero sexual tension even though I think she\u2019s the most wonderful woman alive and tell her so often.<\/p>\n 3 p.m. <\/strong>Voice-note from Natalie. She loves a voice-note. It\u2019s nice hearing her in the middle of the day. I\u2019ve slept with her a handful of times. It\u2019s good sex, and she\u2019s nice company, but the Mia of it all derails me from taking further steps.<\/p>\n 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\u2019ll call to unpack the co-worker conflict after work.<\/p>\n 6:30 p.m. <\/strong>Walk home, which I do almost every day. Sometimes, like today, I\u2019ll stop at a bar, have a glass of wine, and read on my phone. My version of meditation.<\/p>\n 9 p.m. <\/strong>Call Natalie from my stoop. We talk about our relationship. (Friendship?) She calls me \u201cemotionally adjacent.\u201d I tell her I don\u2019t know what that means. She says she loves seeing me, but I\u2019m \u201cout of reach\u201d and she can\u2019t figure out why. I know why \u2026 chaos agent Mia. I don\u2019t say that because it feels mean. I tell her I\u2019ll work on it. Not sure I mean it.<\/p>\n DAY THREE<\/strong><\/p>\n 7 a.m.<\/strong> A message from our CTO: a complicated work thing is resolved. It\u2019s the closest thing to joy I\u2019ve felt all week.<\/p>\n 12:30 p.m.<\/strong> 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\u2019m close with my siblings and many friends, but I feel empty a lot of the time. It\u2019s okay that I don\u2019t have kids, but I\u2019d like to find my person.<\/p>\n 6 p.m. <\/strong>Mia texts, \u201cin the neighborhood.\u201d The West Village version of showing up without warning. She follows, \u201cis that ok?\u201d \u2026 technically asking permission, while functionally assuming a \u201cyes.\u201d I write, \u201ccome up.\u201d We know the drill.<\/p>\n 7:30 p.m.<\/strong> She arrives with wet hair, like she just showered. Odd, because she lives in Williamsburg. The math doesn\u2019t 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\u2019m super-aroused just being near her.<\/p>\n 9:15 p.m. <\/strong>The sex is extraordinary, as always. Tonight, she wants hours and hours of oral. I\u2019m 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.<\/p>\n 11:30 p.m<\/strong>. As she leaves, Mia does this thing where she studies my face for a moment, like she\u2019s trying to remember what I look like in case we never see each other again. I feel good, confused, and slightly like an idiot.<\/p>\n DAY FOUR<\/strong><\/p>\n 7:30 a.m. <\/strong>Pilates at a studio I\u2019ve 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.<\/p>\n 10 a.m. <\/strong>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\u2019m energized.<\/p>\n 3 p.m<\/strong>. Natalie wants to go to Via Carota for dinner, a hard reservation even for me. I tell her I\u2019ll try. Then I ask my beloved assistant to try.<\/p>\n 6:45 p.m.<\/strong> 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\u2019d go for it if I suggested it. She doesn\u2019t want kids. Her age is reasonable. I\u2019m just afraid to cross that line until I\u2019m sure.<\/p>\n 10 p.m. <\/strong>We walk around the city. Why don\u2019t I want to rip her clothes off? Maybe Mia has wrecked me for other women.<\/p>\n 11 p.m. <\/strong>But, of course, we end up at my place. We have nice, slow, emotional sex. It\u2019s not bad. We both enjoy ourselves. Unlike Mia, Natalie always wants to stay over. It\u2019s fine with me. I do enjoy her company. As we doze off, we talk about her family in Cincinnati and how she\u2019d love to bring me home sometime.\u00a0She falls asleep mid-sentence, which is the cutest thing I\u2019ve ever seen.<\/p>\n DAY FIVE<\/strong><\/p>\n 7:45 a.m.<\/strong> 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.<\/p>\n 8:30 a.m. <\/strong>Three-way call with general counsel about a potential partnership. I take it in my boxers in the kitchen.<\/p>\n 11:15 a.m. <\/strong>Shit. The first Natalie text arrives at 11:15. Another at 11:22. She says she\u2019s spiraling a little because I was weird when she mentioned her family. She wants to know if she\u2019s reading into it or if I bumped on the idea. I want to write back but have a call, so I say I\u2019ll respond as soon as it\u2019s over. I don\u2019t want to leave her hanging because I know she\u2019s feeling vulnerable.<\/p>\n 2 p.m. <\/strong>This is my life \u2026 just as I\u2019m about to write Natalie something from the heart, Mia sends a photograph, no caption. I\u2019m aware that Mia\u2019s a big part of this Natalie situation, but I don\u2019t think I have to be honest with Natalie about it. Do I? Instead, I text Natalie that I\u2019d be thrilled to meet her family and apologize if I sounded unenthusiastic. I was just tired from the wine and sex! I\u2019d love to meet them. It\u2019s not a lie. It\u2019s a half-truth because of the messy Mia component.<\/p>\n 7 p.m.<\/strong> Get a glass of wine on my walk home. Feeling torn about Natalie, like it\u2019s time to shit or get off the pot. How romantic.<\/p>\n 9 p.m. <\/strong>Call Natalie to reassure her I\u2019d love to meet her family. We get into it a little. She uses the word avoidant. I tell her I\u2019m working on it (I don\u2019t say \u201cby figuring out my deal with Mia\u201d). We end on a good note: I like her, and she likes me, and we\u2019re excited to advance our relationship step by step. I dread her asking if I\u2019m sleeping with other people, but she doesn\u2019t \u2014\u00a0tonight, at least.<\/p>\n DAY SIX<\/strong> 6:30 a.m.<\/strong> Long run along the river to process. Along the way, I decide to quit Mia and go for Natalie. I\u2019m going to think with my head, not my dick.<\/p>\n 9 a.m.<\/strong>\u00a0Work is work. Overthinking my love life. Part of me thinks I have it good as a bachelor \u2014 the Mia sex is so fucking fun. Then again, I\u2019m lonely. Such a clich\u00e9.<\/p>\n 1:30 p.m. <\/strong>Lunch at a Japanese place. I\u2019m muted and camera-off on Zoom. Order a Sapporo.<\/p>\n 5:30 p.m. <\/strong>Natalie texts: \u201cAre we good?\u201d I write \u201cYessss.\u201d She says, \u201cOkay but are we actually good?\u201d Tell her I\u2019ll call on my walk home. Is she needy or a normal person trying to have a relationship? Briefly tempted to call it all off with both Mia and Natalie.<\/p>\n 7:40 p.m. <\/strong>Natalie answers the phone immediately. I tell her to send me dates for Ohio and I\u2019ll book flights tonight. She loves this. I\u2019m happy she\u2019s happy. (Less happy about an Ohio trip, just because it\u2019s Ohio, but that\u2019s okay.) We make plans for tomorrow night.<\/p>\n 9:30 p.m.<\/strong> Book two first-class flights for Fourth of July weekend. Text Natalie the flight info. Put my phone away to watch a movie.<\/p>\n DAY SEVEN<\/strong><\/p>\n 9 a.m. <\/strong>Natalie and I are going to the farmers\u2019 market for dinner later. I get dressed and walk to Union Square. A full day together is the longest time we\u2019ve ever spent, just us.<\/p>\n 12:30 p.m. <\/strong>My place. After putting everything away, we fool around. It\u2019s awkward in the daylight; I\u2019ve fucked Mia in the daytime, but, with her, the weirdness of being so exposed makes it hot; the weirdness now makes it weird. I can\u2019t stay hard. We take a break.<\/p>\n 2 p.m. <\/strong>She convinces me to see The Devil Wears Prada 2. I\u2019m trying not to think about Mia, which is rough. As I buy movie tickets on my phone, I\u2019m reminded I never responded to Mia\u2019s last text, the random photo. I don\u2019t act on it, but it takes me out of the moment.<\/p>\n 6 p.m. <\/strong>The movie was watchable? We\u2019re home making pasta with lots of vegetables and a side of grilled lamb chops. It comes together nicely. Natalie is a super-skilled chef and I\u2019m a super-skilled assistant. We eat at my kitchen island with wine, a baguette, fancy olive oil. Everything feels natural and nice.<\/p>\n 9:45 p.m.<\/strong> Sex. Natalie keeps trying to slow us down. She wants to \u201cmake love.\u201d I try to be mature and don\u2019t laugh when she says those words. It feels wonderful, however, and thankfully I stay hard until we both come.<\/p>\n 11:45 p.m<\/strong>. It\u2019s hard to fall asleep. I\u2019m not sure what I\u2019m doing. I literally can\u2019t stop thinking about Mia. I miss her. My gut says this could be bad, but my brain says this could be good \u2026 I\u2019ll see how I feel in the morning.<\/p>\n Want to submit a sex diary? Email sexdiaries@nymag.com<\/a> and tell us a little about yourself (and read our submission terms here<\/a>.)<\/p>\n