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The 25-Year-Old Writer Dating an Older Man

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New York’s Sex Diaries series asks anonymous city dwellers to record a week in their sex lives — with comic, tragic, often sexy, and always revealing results. This week, a freelance writer who hikes weekly and wonders what’s up with the older man she’s seeing: single, straight, Bushwick.


7:45 a.m. Woke up a little late today. Oh, the life of a freelancer.

8:05 a.m. A text from Felix. He says to meet him in a cute café right by a park. He just came back from a conference in Florida. I was pleasantly surprised to get daily communication from him during his trip. I think being away from New York helped him realize that we may have something special.

8:07 a.m. I must be one of the only millennial in Brooklyn that does not do online dating. I’ve never done it and this is my reasoning: I think it’s just as hard to meet someone special online as it is offline. Also, I can get a much better sense of a guy in the first few seconds in real life than over days of messaging, so why waste time? But not being on any apps also meant that I am constantly the only single friend in my circle.

Noon On the subway, thinking about Felix. He is Portuguese-American and much older, between the age of 39 and 45, I’m actually not sure. I want to ask, but I haven’t found a way. He has an adventurous spirit and seems to know what he wants. I find that endlessly attractive, but this age difference bugs me. I grew up in the Philippines and the image of an old, white man walking around with a super young Filipina is seared in my brain. It reeks of capitalism and colonialism. Now that I’m seeing an older white man myself, I feel conflicted.

1 p.m. I see Felix crossing the street. He looks like a skinny European soccer player. He has tight, curly hair that he gathers at his nape. No man bun here. In fact, I mentioned man buns and he has never heard of them.

1:02 p.m. He’s all smiles. We kiss. It’s really fucking nice that he kisses me hello and goodbye, every single time. My “relationships” have never lasted more than three months and all of them, by the end, blew up in my face. I have the temperament for a long-term, committed relationship, but things have never worked out.

1:25 p.m. Lunch is going well and we enjoy the unseasonably warm weather. My joke on climate change launches us into a philosophical, political discussion.

2:15 p.m. We are now at a flower garden. It’s just us and two Instagrammers. We PDA intensely in the park. I have no problem being seen or judged.

2:30 p.m. We make tentative plans for tomorrow night.

3 p.m. In a blissed out state on the train. We just connect so well on an intellectual and sexual level.

7 p.m. Back at home. I get a text from Felix saying that since I’m planning to move out of my current place, I should stay at his place longer to see if I like the neighborhood and if we get on each other’s nerves. Mind you, it’s been just about a month since we started seeing each other. I manage to turn the conversation around to planning meeting tomorrow.

9 p.m. About to turn in, but Felix video calls me. We talk for an hour and I fall asleep.


10 a.m. Babysitting. It feels regressive after getting my MFA, but I can’t deny how much I love being around kids, especially after days of solitary writing.

11:30 a.m. I’m always amazed by how little kids eat. I finish off whatever he leaves. What can I say? I don’t have the kind of spare money to order in lunch.

1 p.m. Kid is napping. Felix texts me about a trip his friends are organizing for late winter. He asks me if I would be interested. Does he think we’ll still be together three months from now?

4 p.m. Released from babysitting. I pop into a nearby café to get some assignments done. Felix texts me that he’ll let me know when he wraps up for the day.

8 p.m. Wrapping up dinner with friends. I’m about to head over to Felix’s house when I get a text from him: He says that since I’ll be waking up early tomorrow to go hiking, I can sleep on his couch. This makes me mad. I shoot a short reply saying that I’ll just come tomorrow.

8:10 p.m. He calls. I don’t pick up.

8:12 p.m. He leaves a voicemail, saying that he really wanted to see me tonight and that he’s sorry. Well, then why did you ask me to sleep on your couch?

10 p.m. Lights off. Still angry.


5:20 a.m. I’m up. I go hiking every week. Everyone gets very impressed when I say that. But if it’s something you really want to do, it’s not that hard to make it happen.

6 a.m. Walking to the train.

3 p.m. I find much beauty, wonder and awe in nature. The steady pace helps me forget about my writing, Felix, family, finances, future, climate change, everything.

5 p.m. Done with the hike. I turn on my phone. Nothing from Felix.

6 p.m. Beer post hike. Still nothing. Maybe he’s ghosting.

6:50 p.m. A message from Felix. He is still at work and asks me to let him know before I head to his place. I tell him that it’ll take me two hours and ask if that’s too late for him. He says no, but to please let him know if it gets later than that. I’m angry that he makes it sound like he’s making concessions for me.

7:30 p.m. Heading back to the city in complete darkness.

9 p.m. I go to his apartment and knock. He isn’t here.

9:10 p.m. He arrives and we head in. He gives me the keys to his apartment so that I don’t have to wait next time. The most casual hand off of keys in the history of dating. I’m shocked, but hide it well.

9:40 p.m. I come out of the shower and see he has candlelit the entire place.

9:50 p.m. We talk for a moment and quickly start kissing. It helps that I’m just in a towel. Then he turns me around and we fuck against the wall. It’s super hot. I keep reading in magazines and website about how men love to fuck from behind, but women don’t. It’s my absolute favorite.

10 p.m. He washes off and joins me in bed. We talk about his work and my hike.

10:30 p.m. We are at it again. After a nice missionary session, I turn around and grab onto the bed frames. He takes me from behind. I come. We pause for a bit and he continues to ride me. It feels great. He pounds me, finishes, and falls on top of me. We lie there breathing.

10:55 p.m. He washes off again. I’m exhausted. From the kitchen, he calls out, “Do you want a sandwich?” I say no and fall asleep before he gets back.


8:30 a.m. I’m completely awake.

8:35 a.m. I want to cuddle, but he “needs space” to sleep. He’s completely not used to sharing a bed, which is a good and bad thing, depending on how you look at it.

9:20 a.m. He turns toward me and we start kissing. An unending series of sweet little pecks.

9:45 a.m. We walk to a bakery. We also always hold hands when we go places.

9:55 a.m. He pays for the pastries. This is new. We’ve split everything, even the tiniest thing, so far.

10:10 a.m. Back in the apartment. He brews coffee. We eat and talk about the coming week. I invite him to the variety show I am performing in. He says he’ll come.

12:30 p.m. Back home, to my writing and translation projects.

6:30 p.m. I arrive at my friend’s place for the variety show rehearsal. We decided to add a new part to our piece so we are in the process of improvising and devising. It’s going somewhere, I think.

9:30 p.m. I was wrong. It’s going terribly. It’s bad. I can’t believe we have to perform it in front of people in two days.

10:30 p.m. Back in my apartment, wondering if I am doing everything wrong. Dead tired, very stressed. A text from Felix asks if I’m done rehearsing. I am just too worried and preoccupied to reply.

11 p.m. Lights out.


9 a.m. Wake up late. The combination of hiking, always working, and rehearsing just knocked me out.

10 a.m. Writing, but I can’t seem to concentrate.

11:30 a.m. At a Goodwill to find costume pieces for the show. I came prepared to go to at least four different shops today, but I find everything I need here. At least something’s going right.

12:30 p.m. I finally reply to Felix, saying that I had a late rehearsal.

4 p.m. Too tired and stressed to get any real work done.

6 p.m. At a performance workshop run by a friend of a friend. I always don’t want to go, but once I get there, I have such a great time.

10 p.m. Still nothing from Felix.

10:40 p.m. Lights out. I lie awake, making a mental list of things I have to do. What am I doing? I should be sleeping. So I watch a little porn, masturbate, and fall asleep.


6:45 a.m. Day of the show. I create a list of things I have to get done today.

11 a.m. Hustling, writing, getting shit done. I’m running on adrenaline.

2 p.m. Still nothing from Felix.

6 p.m. Final rehearsal. Things are going well, though we need to find an ending.

7:45 p.m. We arrive at the venue to through our piece in the space.

7:50 p.m. I cave in and text Felix to get a sense of where he is.

8:30 p.m. We step outside to work out an ending for the piece. Passersby give us weird looks. We arrive at a simple, genius idea. Awesome. I check my phone. Still nothing.

8:40 p.m. Felix finally texts back. He will be there a little after nine. I’m all nerves.

9:10 p.m. The show is about to start. Felix wanders in. I light up.

9:20 p.m. We do our piece. Crowd roars with laughter. This is great.

9:40 p.m. Intermission. I say hi to all my friends and introduce Felix. He’s acting a little odd and on edge. Maybe he’s nervous?

9:55 p.m. We perform our next piece. Lots of reactions. I can tell it made people think. The ending worked out perfectly.

11 p.m. Show ends. We all mingle. Felix says that my piece was “hot.” I ask him if he minds if we hang out for a bit. He says yes, he minds. He has to wake up early tomorrow. I push back because I wasn’t brought up to be like, Yes, dear.

Midnight Finally heading home. He does seem tired. Adrenaline wears off and I am also completely beat.


7:30 a.m. I lied. Adrenaline has not worn off. I’m wide awake.

8:40 a.m. Felix stumbles out of the room. I make us breakfast and coffee.

9:15 a.m. He invites me to a dinner he’s having with his family next week. I say yes, but I’m freaking out a bit. I don’t mind meeting his folks. It’s just that things are going a little fast. We’ve only known each other for a month.

10:35 a.m. Babysitting. The kid is in a mood today.

2 p.m. She insists that she does not want to take a nap, but falls asleep. Typical.

4:40 p.m. At home, prepping my bag for another hike.

5:30 p.m. Sunset is gorgeous today. I text Felix. He says to send a picture and asks if I want to come over tonight. I say I’m hiking, so no. I’m not going to stop doing things I like just because there is a guy in my life.

6 p.m. Dinner time. No new texts from Felix. Our age gap pops in my head again. To tell the truth, I feel more empowered in this relationship than any other ones I’ve had with guys my age. I don’t have to watch what I say in fear of hurting his fragile ego. I can challenge him and let him stand up for himself. But things are moving quickly and I’m feeling vulnerable. I hope that soon I’ll figure out where I stand.

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The 25-Year-Old Writer Dating an Older Man