In this week’s story, a woman gets ghosted twice, then flirts with a guy who’s more interested in her friend: 40, single, New York.
DAY ONE
8:30 a.m. I’m on a crowded subway going to work. All I want to do is sit down and read my book (Tomorrow and Tomorrow and Tomorrow) but there are no seats and it’s packed. I hate everybody. I’m in a terrible mood.
9:30 a.m. Finally settled into my work desk. I’m a PR director, mostly working in hotels and hospitality. My clients are almost all nightmares. I’m not always such a bummer, I’m just over everything today.
1 p.m. I leave my desk to go to the nearest Chopt. A few minutes later, with a salad that costs about a hundred dollars, I sit outside in a park and start to swipe. I can’t believe I’m still in the swiping game. I often wonder how many hours of my life it has sucked up. That makes me feel super depressed. I had a date three nights ago with a guy, Mark, who I really liked, and who I thought liked me, and who I slept with — who is completely ghosting me. It’s really thrown me off.
5 p.m. My boss is going on maternity leave so we’re doing a drinks thing for her at the office. It’s kind of counterintuitive since she can’t drink, but I welcome the bubbly. I really like my boss, we’re close. But I can’t lie and say it’s not hard seeing yet another friend or colleague become a mom while I’m stuck online dating with no luck.
8 p.m. Go to the gym and swipe from the treadmill. Then I do the sauna and swipe when I’m out.
10 p.m. Now I’m trying to watch Real Housewives but swiping the entire time. I just really, really, really want to meet somebody. I’m lonely.
DAY TWO
9 a.m. On Tuesdays, I have therapy. My therapist is so sweet. We’ve been together for five years. Sometimes I wonder if she just tells me what I want to hear though. Like, why is nothing changing for me? The last boyfriend I had was about seven years ago. I wasn’t attracted to him, but he was very smart, kind, and funny. We met at a singles event and dated for about two years. I never enjoyed the sex. It was kind of gross to me because I found him so ugly.
11 a.m. During my session, we talk about casual sex. I am in my slutty era and not sure if it’s working for me. I’m finally enjoying sex and getting to know my body — given everyone on the apps is kinky and super sex-positive, which I like a lot — but I also really struggle with fucking someone and then never talking to them again. I guess you can call it some kind of anxious attachment, but honestly — isn’t it normal to expect to talk or date again once you’ve had sex? Sometimes I feel like I’m dating on my own frequency. The most obvious things — like calling someone once you’ve been naked with them — aren’t guaranteed. And then you say something about it and you’re the psychopath?
5 p.m. Work entails a ton of Zooms with hotel owners and managers who expect the world. My job is cool because I travel a ton, and for free, but it’s also a slog. Clients are never happy. And we always hate our clients. It’s never exactly a nontoxic work environment, despite all the five-star hotels and car services. And yet I love what I do. Who gets to travel so luxuriously for free? Maybe I have figured it all out after all.
7 p.m. I’m meeting some travel writers for a drink after work. These are girls I used to party with. Now they are all married and on their first or second kid. I’m happy to see them but feel bored by their parenting stories.
10 p.m. I’m chatting with someone, P, from the apps. He seems like my speed.
11 p.m. Still chatting! He’s a lawyer. He’s Catholic. He’s … into chokeplay. I tell him I am not. He says that’s a dealbreaker! Okay, bye, P.
DAY THREE
7 a.m. I’m up early to put an hour into the apps. It’s seriously a part-time job if you really care about meeting someone. I keep seeing flashes of Mark and our night together and the sex at his place. Is it possible I was bad in bed? Did my breath stink? We bonded over politics and religion and laughed a lot. The sex was good … I mean I was kind of drunk so I don’t remember everything, but I know he wore a condom and came? Why would he never want to see me again? I’ve texted him three times since the date. I can’t text him again.
9 a.m. At work early, following up on the leads the travel writers all shared with me last night. They all want free trips, even the ones who work for places that don’t allow free trips. I’m fine with it. That’s how my business works. I get these writers to sexy and exotic places, in the most first-class way, and they write about my clients.
2 p.m. At lunch I follow up on some messages from the guys on the apps. The most promising one is named Zach, another lawyer. From my Googling it looks like he’s insanely successful. Very rich and divorced, looking to settle down again. I like it all.
5 p.m. As I wrap up a Zoom with a client, Zach asks me out for tomorrow and suggests an impossible-to-get-into restaurant. This gives me life. I just need something romantic and sexy to look forward to.
DAY FOUR
9 a.m. I have nothing to wear tonight so I’m banging out as much work as I can to make time for a trip to Bloomies later. I recently lost a lot of weight thanks to Ozempic so I never have anything to wear, nor do I know my style now that I’m living inside a new body.
And while I’m happy to be thinner, the truth is that it hasn’t made dating any easier. Men are still jerks. The good ones are all taken. I don’t swipe more or less since the weight loss, I just get more responses and positive attention, at least in the very beginning.
11:30 a.m. My client just asked me to get four top-tier journalists to visit the property — in Europe — in two weeks. TWO WEEKS. It’s going to be impossible. The best writers for the best publications have lives. They have kids. They have commitments. I spend the rest of the day calling my contacts.
3 p.m. A quick run to Bloomingdale’s. I buy a black bodysuit and a pair of flared jeans. Standard skinny-girl date-wear. A new phenomenon for me, but I’m happy about it.
6 p.m. I’m lucky that my office and my apartment and where we are going tonight are all close by. It’s a very midtown existence. I get to shower, do my glam, all of it. In the end, I smell like demure French perfume, and I feel pretty!
8 p.m. Zach is … not what he looks like in his pictures. However, he is confident and he has swagger and I’m not exactly repulsed by him. The restaurant is a home run and I kind of can’t believe I’m here. We have a martini at the bar first, and then make our way to the dining area. We order steaks and more martinis. I’m having a marvelous time.
10 p.m. We’re tipsy and talking about sex … not like dirty talk, more about modern sex and dating. He confesses that he has an STI. I admire his honesty and tell him it’s not a big deal. I actually really like him, at this point in the night, and am curious about kissing him and if we have sexual chemistry. Okay, in other words, I’m horny!
10:30 p.m. Zach has his driver drop me off, and then drop him off. In the car, there is no kissing. No hook up. Nothing. I can’t believe it. He talks to the driver about the stock market. I honestly cannot believe it.
DAY FIVE
10 a.m. Today is sort of a low point for me.
12 p.m. Trying to act like myself at work but I just feel like the ugliest, loneliest woman in the world. Zach was, by all accounts, a vile man and even he did not want me.
4 p.m. I sneak home for a nap before a client dinner tonight. I just want to hide from the world. I smoke a tiny joint just to knock me out for a bit and set my alarm.
8 p.m. Miraculously, I’m showered and refreshed (ish) for this client dinner. I find it all pretty painful — and of course I did not hear anything from Zach today — but this particular client has a property in the Caribbean that I want to visit, so I throw in some charming banter with hopes I’ll get there this winter.
10 p.m. Go to bed. It was a bad day. I know it won’t be like this forever.
DAY SIX
9 a.m. It’s the weekend, which means I’m hunting for guys 24/7. It starts with coffee at a cute café nearby. I bring my book and sit at the bar.
11:30 a.m. Texting with a guy from Hinge who wants to meet up later. He suggests we meet at Burger King. For real. I stop responding.
3 p.m. I meet my friend, Allison, at one of those chic sex shops in Brooklyn. We both buy new vibrators. Allison is single but her lifestyle is so much different from mine. She sleeps with men and women. She has crazy, hot sex. She is always busy and blowing people off. I wonder if she seems this way just because she chooses to see, and frame, her single life like this — I could present my life in the same woozy, free-spirited way? Or maybe she’s just hotter and more fuckable and more chill.
8 p.m. I live near a trendy restaurant with a good singles scene, so I go there for a glass of wine. There are three guys at the bar next to me, but I think they’re all wearing wedding rings. One of them asks what’s good on the menu. I tell him about the kale salad. He’s clearly the single one — his name is Harry. We all start talking. Harry is cute but I can’t see myself fucking him; he’s quite petite. Eventually I try to settle up for my two glasses of red wine but the guys say they’ve got it. That’s nice. I still won’t fuck Harry.
10 p.m. Watch TV and fall asleep. I remind myself that I won’t be alone forever.
DAY SEVEN
10 a.m. As I’m making a second French press, Allison texts that she has an extra ticket to a singles event tonight at some comedy club. I’m in!
1 p.m. Attempt to go on a jog. I lasts 12 minutes. I pivot and run to Trader Joe’s for some groceries; maybe I’ll cook some meals for the week.
4 p.m. Allison suggests we get drinks before the comedy singles thing. We pick a place and I start getting ready.
6 p.m. The bar we’re drinking at is filled with gorgeous men and … they’re all 22. It must be an NYU scene. I feel old but try to stay positive.
8 p.m. The comedy show is funny and the crowd is good! It’s interesting how sexy people are when they’re laughing. Everyone around me is radiating good vibes. I am crushing on the guy behind me who is laughing so hard he’s practically exploding. I find it charming.
9 p.m. Guy behind us is named Beau and he’s single and cool! We end up exchanging numbers. The only red flag is that he is moving to Los Angeles in the spring. This came up because Allison is from L.A. It’s not really a red flag, but more like an, “of course.” Nothing is easy for me. Beau is a talent agent, which I think is a hot job. I wonder if he will call me.
10 p.m. On the way home, Allison tells me she thought Beau was kind of into her. I was like, “Oh really?” She’s like, “You don’t care if I meet up with him later, do you?” In fairness, I never told her I was into him. And she didn’t see us flirting … she was talking to someone else when it happened. It makes me want to cry, but I tell her to go and have fun. What else can I do, yell at her? I get off on my subway stop while Allison probably goes to fuck Beau. This is my life. I am not sure what to do next. Other than fire my therapist.
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