Retired person having sex at her boyfriend’s office


Photo-Illustration: James Gallagher

This week, a woman plans romantic trips with her boyfriend while worrying that he’s excluding her from her family life: 52, in love, New York.


9:05 am The oat milk latte from the espresso shop downstairs has opened. I usually don’t like spending that kind of money on a cup of coffee, but lately I’ve been feeling inspired with life. Why? Because I’m having the best sex I’ve ever had. And I’m 52!

11:11 am I wear clothes for hiking. I live in the West Village and like to walk to at least Flatiron, then back to Tribeca and back again. I have loved the city as long as I can remember. It is the only love that has always lasted for me.

2 p.m Walking is done. I showered and sent a nude photo to T, my new boyfriend. He is divorced, successful and very sexy. I’ve never been married, and a part of me thinks it’s all on purpose leading up to meeting him. He wrote back, “You’re damn charming.”

5 p.m Tonight T has dinner with the children – they are in their 20s and working in the city. We’ve been dating for six months and I’ve only seen them a few times, mostly by chance. That was a sore point for us. I feel like he’s preventing me from seeing them and that hurts my feelings. He says it’s delicate because they’re much closer to their mother and he’s in the process of rebuilding his relationship with them and bringing in a new girlfriend could get in the way of that. To be honest it sounds weak to me… but I try to respect that. I’ve never had children and that’s a huge regret, so the chance to become a stepmother or one day become a grandma is a great concept. But again, I try to play it interesting on the subject.

9 pm I watch an episode of Dopesick. It’s a very disturbing and wonderful TV, in my opinion. I used to be a TV producer. I made a lot of money from several programs and now I consider myself retired. When I fell asleep, I thought about having sex with T. Then I popped a piece of sleep gum and slept like a baby.


10 am I recently invested in some new sex toys. I play with some of them myself, but first I send T a picture of them lying on my bed. He’s coming tonight, so he texted back so he wouldn’t touch anything. I stopped masturbating. I like that kind of gentle domination.

3 pm One face and one stroke. The perks of being in your 50s and creating a good life for yourself. I have no complaints about my age other than regretting not having children. I should have done it alone. I’m busy working and working crazy. I had a lot of fun and fast flying times and before I knew it, half of my life was over.

5 p.m I started cooking for T. I’m a good cook, another trait of not having children. I was able to cultivate hobbies like cooking and fine wine. Tonight I will make lamb chops with other Mediterranean dishes. T will bring wine – he’s a booze snob.

7 pm He is here. He’s gorgeous. We’re working and I want to fuck right away. He’s at work (he’s in finance) and needs to relax a bit first. We had wine and I ordered dinner out. I’m very upset, but I can wait.

9:30 pm We are making great love in my bed. We use some of my sex toys on me – he doesn’t like any of the toys on his balls or ass, which is fine with me.

10 give me We both arrived, almost at the same time. T fell asleep and I went to the living room to watch another episode of Dopesick.


9:15 am I don’t want to go to plagiarism class, but I do. My best friend, D, and I never miss this Wednesday class. D is married but has always had an affair. I don’t know how she handled this but her husband either doesn’t know or doesn’t care. I don’t think he cheated on her, but who really knows? We all have secrets.

11 a.m D’s latest affair was with a couple. I’m obsessed with the logistics of it all. Their sex involved a lot of weed smoking and surrender. Neither are my favorites, but their own.

3 pm My friend X offers me wine and cheese. X is in the alcohol business. I love her, but she’s the negative type. She likes to suspect that T won’t integrate me into his life with his kids. I know it’s a bit odd, but I don’t think it’s a giant red flag either. We only met six months ago through a matchmaker. We have no reason to rush. We are on a different path. I have absolutely no interest in a husband – if it were me, I would have been married a long time ago. However, X has a way of making me feel a little nervous about things. Is there a word for this type of friend… is it a saboteur?

9 pm I just spoke with T. We talked about our days and we also planned a little trip together. We’ve done weekends before but never had anything to do with airline tickets. We’re a COVID relationship, so that wasn’t available on the map until now. Now we plan to go to the Bahamas in February and then to Paris in the spring. T is really excited about our trip and I take that as a very positive sign. X and her negativity can suck it up.


8:20 am I have a work coffee meeting today. It’s for a project I might be interested in helping out with.

10 am The meeting was strange. The woman at the head of the project was very upset. I think I will pass.

12 pm I stopped by T’s office because of my recent meeting. It was almost empty there because of COVID hours. I go crazy when I see him at work. I suggest we find a private place to fool around and the only place he can think of is the bathroom. Everywhere else there are cameras.

12:15 pm We were making love in the bathroom and it was so hot I couldn’t even stand it. I caught T pulled out and to all my black pants. I want to go home with his marks on me. He doesn’t like my outfit at all.

2 p.m We grabbed a quick lunch.

3 pm I walked home in cum fur and smiling ear to ear.

9 pm More travel plans with T on your phone. I am very excited about our future.

Mother’s Day

10 am I’m scrolling through Facebook looking for something in the new apartment. I see a lot of my exes on Facebook. I am friends with most of them. Sometimes it feels weird that everyone has moved on and started families and bigger jobs and here I am, basically who I am, but then I think this has always been my path. I’ve always been pretty happy – if my life bores me in any way, I’d change something.

2 p.m I downloaded an audiobook and walked to Central Park and back.

5 p.m I make a monster bowl of pasta with butter and delicious Parm. I have earned it. I poured a glass of red wine.

7 pm T is with the children tonight. I felt a bit left out so I popped an early sleep gum and closed it.


9:20 am I got to see an old fire for brunch today. Let’s call him F. I know he’ll want to make love. T and I have never really discussed our rules about sleeping with other people. That conversation always made me feel juvenile to me. I know we’re “exclusive” to each other and I know sleeping with someone else would be bad, but I can certainly justify it. I’m not sure how I’ll feel after seeing this guy.

11 a.m F looks good. He’s Italian with great hair and a man, he loves sex. I can picture him undressing me as we strike up a conversation with our significant other (he also has a new relationship). We were staying near the Wythe Hotel and as expected he offered us a check in.

12 pm I’m thinking about it, I told him.

12:30 pm Another apricot tree. This makes three.

2 p.m We are doing outside the restaurant. He is an incredible kisser. I told him we had to stop and I took a taxi the old fashioned way.

3 pm I’m smiling thinking about late breakfast. It’s like the old me, a little reckless, but also completely harmless. I don’t even think I violated anything with T. All is well.

9 pm I used a vibrator and imagined what would happen if we checked into a hotel room. I came very hard. And… turn off the lights.


10 am T has officially booked Bahamas tickets! I am really excited.

11 a.m I sent T a text suggesting that I bring his kids to a small celebration next week. I want to cook for them and their partner or friends, whatever. T said it was a great idea but I felt a bit of air around me, and that was a bit of a pain.

3 pm I texted T about the holiday party. He asked if they were around? Can I include it in my calendar? I want to start planning the recipe. He gave me a vague answer – implying that he wasn’t sure if it was a good idea and that he hadn’t texted them about it – and now I officially want to cry. I try to focus on the Bahamas.

5 p.m I have to meet T for dinner tonight. I’ve never done this before, but I abruptly canceled him. I came up with an excuse to send a text that might be true, but it also pissed me off.

6 pm T call me. He knows I’m upset. He wants to talk. I appreciated that he wanted to communicate with me, but I told him that I wanted to speak in person. I don’t want to sound smug about his kids. It is a sensitive topic. I suggest we meet tomorrow so I can spend the night gathering my thoughts.

9 pm Masturbation or Dopesick? I go to watch TV. I get sick of thinking about love and sex.

10 give me T texted, “I’m here to talk whenever you’re ready. I love you. Good night.”

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