The Woman Firing Her Fancy Matchmaker

Alyssa Shelasky · 2026-02-14T00:00:37.607Z

This week, a recruiter has sex with an interesting guy she meets at a party: 56, single, New York

7:05 a.m. I had a bad night’s sleep. For no good reason at all, I stayed up online shopping past midnight and ordered hundreds of dollars’ worth of clothes. I already know I’ll return every single item. I do this. When I’m antsy, I online shop. It’s not good. Lately, I’ve had low-level, relentless anxiety. I can’t attribute it to anything in particular other than maybe being an empty nester.

8 a.m. Catching up on Nancy Guthrie updates (horrifying, heartbreaking, I can’t look away). I shower, wash away the cobwebs around my brain, and start the day.

11 a.m. I own a recruitment firm specializing in high-net-worth women. I match powerful CEOs with powerful companies. Today, I have to book trips to the West Coast with clients.

I’m trying to coordinate my travel so I can see my kids, who both go to college there. My ex-husband lives in L.A., and he’s an incredible support system for them when they’re on his turf, but I miss the hell out of them. I’ve been divorced since my kids were toddlers. Almost 20 years. He had an affair with my best friend, my life blew up, and over time … we’ve all gotten over it. Ex-best friend and ex-husband got married, had kids, and are still happy and going strong. Good for them. Truly.

4 p.m. Leave to meet with a matchmaker. I’ve hired matchmakers throughout the years, as I’ve been “looking” for decades now. This one is unique because he works with people all over the world and helps facilitate dates in other countries if the situation seems promising. We’re meeting at a coffee shop close to my apartment on the Upper West Side.

5 p.m. Matchmaker says flattering but insulting things about my appearance: “Wow, you sure haven’t let your body go!” and “You’re beautiful … for someone in their 50s.” It costs nothing to work with him. The men pay for his services, not the women. He has a guy in London who he says would be perfect for me, so I deal with his terrible personality for the sake of love.

10 p.m. I talk to my kids on the phone almost every night, then watch an hour of TV (tonight, it’s Shrinking). Contemplate grabbing my vibrator, but I’m not in the mood. I very much crave a good fuck, but I’m not embarassed to say that on most nights, sleep is more pleasurable.

9 a.m. Micah, a friend who never married and still thinks being a “modelizer” is cool, texts about a party tomorrow to celebrate someone’s divorce. I’m off the apps, meaning I have to go out more. Tell him I’m a “strong maybe.”

11:30 a.m. Sophie, my sister, also has an event tomorrow night. Hers is more corporate — she works for a New York sports team. Now I have two things to look forward to.

5 p.m. In the freezing cold, I walk to J.Crew and Zara. All my clothes are big on me, and I don’t know why I’m losing weight. I’m never hungry. Food doesn’t excite me like it used to. Okay, maybe I’m depressed. For now, let’s assume it’s the winter blues.

9 p.m. The matchmaker says the Londoner wants to meet, but before flying here on his plane to do that, the matchmaker would like us to FaceTime. We set that up for tomorrow morning. As I cut the tags off a sea-green velvet J.Crew suit, I allow myself to think Londoner could be the one. It has been years since I’ve had a crush, but I refuse to give up hope. Twice a year, I’ll find a great fuck, either at a bar or maybe via a random online connection. They’re glorious, intense, then over. I’ve never wanted to date any of them. I consider these fucks reboots.

11 p.m. In bed, I do a Google search on the Londoner. He’s quite ugly, to be frank, and very rich. Historically, I’ve never been able to date gross but loaded men. I’m not even a little bit of a gold digger. I wish I were! He is tall and has a very interesting life. He’s had two wives who look normal and beautiful, so there are obviously women who’ve wanted to fuck him. So, yeah, I’m more excited than not.

9 a.m. A massive delivery arrives. It’s the clothes from my online binge. I completely forgot I ordered this stuff.

10:30 a.m. Giving a talk at a private high school about female empowerment. I do this once a month, so public speaking doesn’t make me nervous. The person, Drew, who coordinated the talk, uses they/them pronouns and is around my age. As they get me settled, I feel a bit of a vibe. I was a lesbian in college, long before everyone was “queer,” but settled down with a man. Now, I’d label myself bisexual, but my kids don’t know that, nor do I announce it to anyone. Drew asks what my husband does. I get a little jolt from looking them in the eye and saying, “I’m single.”

1 p.m. After the talk, Drew asks if I’d like to meet up sometime for a glass of wine. I’m taken aback at their forwardness, especially because we’re inside of a high school. They’ve done nothing wrong; I’m just thrown a bit. I tell them to email me and we’ll “set something up.” As I walk away, I regret sounding cold.

3:30 p.m. Answer about 300 emails, mostly about this one company I work for that’s restructuring in a very public way, then get ready to meet Micah at the divorce party.

5 p.m. I had no idea I was walking into this. It’s a loud group of divorced women celebrating this other woman whose divorce became official. Everyone gives her corny dating advice. I’m all for self-empowerment, but these women are like cartoon characters. Have a glass of wine with Micah, who is a pig in shit being the only straight guy in the room. Text my sister about her event. I can’t get out of here fast enough.

7:30 p.m. I’m the first person at this private club in Soho, but it’s too damn cold to linger outside. The next person who walks in introduces himself as Peter. He looks like a former baseball player. He’s not wearing a ring. We have a flirty conversation. I tell him about the divorce party, and he says he’s been divorced so long that he almost forgets he’s divorced. It’s funny, but I feel the exact same. By the time my sister arrives, I’m locked into the idea of having sex with Peter. She tells me he’s a good guy, from the little she knows, and is a lawyer for a popular athlete.

9 p.m. Some sexy younger women join the party. My heart sinks when I see Peter talking to them, but he keeps looking over as if he’s trying to tell me something, and we’re smiling at each other.

10 p.m. I’ve had two large glasses of wine. If I have one more, I’ll be drunk. Then again, if I have one more, I’ll find a way to fuck Peter. My sister, who knows me better than anyone, gets me the third drink.

11 p.m. The party’s over. My sister calls a car to go home to her husband and kids uptown. Peter asks for a “nightcap at his place.” We don’t even pretend it’s anything else.

11:45 p.m. After a quick tour of his apartment, which is modest but lovely, we kiss. He smells like whiskey and laundry detergent. He undresses me in his living room. Our bodies are a bit saggy here and there, but that only draws me to him more. We have sex under his sheets. He’s big and hard, and I come in two seconds. After he finishes, we laugh and blush. I get dressed, give him my number, and go home.

6 a.m. Wake up with a vicious hangover. My headache is so bad that I can’t even think about the sex last night. Hangovers are the worst part of getting older. Take two Tylenol and go back to bed.

9:30 a.m. Up and feeling better, but not great. I move my morning Zooms so I can deal with my hurting body first.

1 p.m. I’m showered and an iced latte is on the way via DoorDash.

3 p.m. A text from the matchmaker: “Are you on yet?” I have the FaceTime with the Londoner right fucking now! I tell him that I have a family emergency and have to push it … I hate doing this, and I accept that I’ve probably blown it, but I look awful and can’t function yet.

7:45 p.m. Text from Peter: “It was great meeting you! Let’s get dinner sometime?” I’m thrilled, but still feel shitty and don’t respond.

8:30 p.m. Text from Drew: “Wine. When?” The word wine makes me want to throw up. Also don’t respond.

9 p.m. Take a gummy and crawl into bed.

8 a.m. Make coffee and rejoice in feeling human. Now I can process the Peter of it all. He’s age appropriate. Divorced since forever, so no drama. Loves his kids. Great career. Amazing sex. What’s the “but”? There’s gotta be something.

11:50 a.m. While on a Zoom, I turn my camera off and repackage the clothes I bought online. They’re all going back. One day, Revolve will ban me from toying with them.

1 p.m. Write back to both Peter and Drew with my availability. I’m not really into Drew, but in my experience, juggling two people makes you extra desirable to both. They can smell competition. Hmm, who will respond first?

1:10 p.m. Peter! Wow. No game playing. Love it. We settle on two nights from tonight. He asks if I have a favorite restaurant near my apartment. I love that; we both know the key is “near my apartment.” Tell him about a trendy Italian restaurant, and he says he’ll make a reservation. Sexy.

5 p.m. Drew invites me to a comedy-plus-poetry thing tonight. It doesn’t sound like my thing. I make up a lie about a work deadline. They heart it. I can table Drew for a few days.

8 p.m. Call the matchmaker back and he reams me out for missing the FaceTime. He says that the Londoner was really turned off. I basically tell the matchmaker to fuck off. Life happens. I can’t handle rigidity in friends, colleagues, lovers, or matchmakers.

9 a.m. My son is flying home from college for a few days to interview for a summer job. Get his room ready and go to Whole Foods to stock the fridge with his favorite foods. Lots of kale, apples, and blueberries, plus an apple pie and some vanilla ice cream. He gets in late, but I’d like to be home when he arrives.

10:45 a.m. Text Peter that my son is coming home, so our date needs to “wrap up” around 9. He writes back that I’m a great mom. He asks if tomorrow is better, and I imply tonight can be a quickie. He seems amused by my forwardness. We move our date to a late lunch. Same restaurant, less food.

3 p.m. Peter is at the restaurant first. He looks different in the daylight. Less hulking and “masculine,” more like a divorced dad. Still handsome. We kiss — on the lips! — and order white wine and olives.

4 p.m. When my glass is finished, I touch his thigh and say, “Let’s get out of here.” He pays the bill and we bundle up. It is impossible to look good in all these layers, so I walk as fast as possible to my apartment five blocks away.

5 p.m. I don’t even show him around. We’re ravenous for each other. I love how much he wants me. Sometimes, sex feels transactional, but this man wants to devour me.

6 p.m. We get dressed and I rush him out the door. It’s like we’re teenagers, and it makes me mischievous and giddy. There’s a lot of laughter and hugs. I’m happy.

9:30 p.m. My son arrives. He’s so sweet. He’s starving, so I make him a meal and we eat the pie as we catch up. I tell him I’m “seeing someone” but it’s very new. I don’t let on that he was here three hours ago or that Peter is the lawyer for an athlete my son has always loved.

8 a.m. Incredibly joyful waking up with my son in the other room. Go to the kitchen and get into the same routine we had when he was young. Tear up a little about how time is flying.

11 a.m. My son wakes up. Peter texts: “Good morning.”

4:40 p.m. Doing my son’s laundry and buying essentials for his dorm while he visits high-school friends who go to college in the city. This day feels warm and right, even though it’s literally -7 degrees out.

6 p.m. My son is still out, so I text Peter that I can’t wait to see him again.

9 p.m. Drew asks if I’m interested in spending time with them or not. It’s a bit aggressive, which I admire, but the truth is … I want to play this thing out with Peter. I tell them that life is hectic right now, so let’s try to reconnect in the spring.

10 p.m. My son is home. We sit at the kitchen table and he fills me in on all the gossip about his friends. He asks about my job and my life at home as an empty nester. I tell him about the athlete who Peter works with. His eyes light up. “Mom,” he says, “you have to marry this guy.”