This week’s sex diary.
In this week’s story, a self-made businesswoman tries to date like it’s her second job: 35, single, Brooklyn.
DAY ONE
8 a.m. Hot Girl Summer has taken on a new meaning as I wake up sweaty. I don’t know if it’s the two glasses of wine I had last night or the scorching temps, but I am drenched.
10 a.m. Drinking coffee and sitting in my little home office. I have my own marketing firm, with a few employees who all work from home and a dozen clients. Most of them are in fashion and beauty, which does not mean anything about the job is frilly or glamorous. It’s stressful running your own company, and I take it seriously. However, since I’ve been single for the last few months, and I would like a relationship, I’m really trying to date like it’s my (other) job. Doing both at once has been a lot. I’m burning the candle on both ends.
3 p.m. I’ve put in a few good hours of work, so I decide to walk outside for an hour for some exercise. I hate gyms and hate working out, so my daily walks are a way to move my body and stay healthy.
7 p.m. Tonight I have a date with Luca. He’s a random guy visiting from Italy. The only reason I’m bothering is because his online pics are so insanely hot. I am dating to find a boyfriend, for sure, but sometimes I think these one-off random dates are good distractions. If I’m so focused on boyfriend-hunting, it probably won’t happen, right?
7:30 p.m. I meet Luca in the city, which is annoying, but he wants to try a trendy bar downtown that’s on his must-see list. I see him when I walk in and I’m immediately not into him. Everything he’s wearing is skintight. He reeks of cologne. Even his accent is throwing me.
8 p.m. After half of one drink, I tell him that I have a horrible migraine and have to head home. Hope it doesn’t hurt his feelings, but I just can’t stay another second.
9:30 p.m. I’m home and feeling sad. I really don’t like being single. I’m trying everything I can to meet someone. It’s really frustrating and hard, and nights like tonight just bum me out.
DAY TWO
8 a.m. Wake up feeling fresh and ready to dominate at work. I have a bunch of meetings to bang out.
1 p.m. As I wait to meet another client for lunch, I quickly make plans with a guy, Jack, I met on Hinge. He is in finance, and divorced, and very handsome. He’ll probably be a player, but you never know. We’re going to have a drink tonight.
2 p.m. When my client gets up to use the bathroom, I quickly make wax and blowout appointments for tonight. This date-preparation shit gets so tedious. I can’t wait to be in a relationship where I don’t have to think about outfits and appearances.
My last relationship lasted two years and ended a few months ago. My ex was not ready to get married or have kids, and as much as I begged for it, it just pushed him away. Eventually, I had to accept that things were not going anywhere with him. The hardest part about leaving him was the sex. We had amazing sexual chemistry. I came, like, three times a night with him. He made me feel really horny. I haven’t felt that way since. I’ve had sex with about five guys since the breakup and my orgasms were all pretty mild, if they happened at all.
6 p.m. All groomed for Jack. We decide to meet for martinis at a restaurant in Brooklyn that is near my apartment.
We walk in around the same time. He’s super handsome and has a nice and boyish face. I mean, he has slight American Psycho energy, but he also has some Future Husband vibes. We’ll see which one wins.
8:30 p.m. It’s a great date. We are two martinis in and eating steak-frites at the bar. Our legs are touching, and I feel some heat. Now that we’re all loose, we start to talk about our lives. Jack tells me his ex-wife cheated on him and that it’s been pretty awful getting back on his feet. Trust issues. Anger issues. It’s obvious that he’s “doing the work” — but is he too damaged? I tell him that I’m very sexual and since my ex, I have yet to find someone to “make me happy and make me come.” He likes that …
10 p.m. Cue to my apartment. Jack is an athletic lover. Very physical. It’s not tender or emotional in any way, but I’m okay with that for now. This issue is … his dick disappoints me. It’s too thick. I know some women are into that, but it’s just not my thing! Regardless, I ride it for an hour and we both get off. Jack asks if we can hang out again, and I tell him I’ll think about it. I’m being flirtatious, but I actually do have to think about it.
DAY THREE
8 a.m. These hangovers have to end. I’m taking a break from drinking.
10 a.m. Feeling kind of dirty after the Jack date. He unloaded all his problems onto me and then hauled out a big troll of a penis. I feel depressed. I know it’s the aftermath of the booze talking.
1 p.m. I learn we won a high-paying account that I worked really hard to secure. It’s a game changer for my business financially, so I try to celebrate the victory. I take myself out to lunch and order a salad Niçoise at the bar. I wish I had someone to share these moments with.
3 p.m. Clean my house while taking a call on speakerphone. Tonight, my sister is coming from Philadelphia, where she lives with her husband and kids. I need to do some adulting by way of expensive groceries and fresh flowers so she can see how successful and sophisticated I am!
5 p.m. My sister’s train is here. I try to figure out where we should have dinner. It’s hot out there.
7 p.m. It’s great to be together. We end up at a Middle Eastern restaurant, where she drinks wine and I get sparkling water. I love being on a date with her and not some random man.
9 p.m. As we watch reality TV together on my couch, she takes my phone and explores some of the guys online for me. She forces me to chat with Max, a guy who looks way too frail for my liking, but she says her sister intuition says he has potential.
11 p.m. We go to bed, and I feel proud to have a second bedroom with a comfortable bed for her. I bought my apartment with my own money, every cent of it earned by me during COVID. I try to remember to be grateful for things like that.
DAY FOUR
9 a.m. My sister has to go home to her family, and I have a monster day at work, so we hug good-bye and I send her off.
1 p.m. I make a date with Max for tomorrow, but tonight, I arrange to have a coffee with someone named Jay, who seems really cool. He’s giving Pete Davidson vibes, but hopefully he’s a little less … edgy?
4 p.m. Good talk with my accountant about the business. It’s going to be a solid year!
6 p.m. I don’t want to drink coffee this late in the day, but Jay has “sober” in his profile, so I assume coffee is his best first-date option. As I wait for him at this cute coffee shop in Greenpoint, I get a feeling that it’s going to be a good night.
6:15 p.m. Jay apologizes for being 15 minutes behind and says that his shift ended late and he wanted to shower before meeting me. He’s a social worker and works at a hospital and has a really interesting job helping patients in need. I’m totally fascinated by it, which never happens with the bankers and lawyers I meet. Also, did I mention that Jay is hot? With a really sweet and warmhearted personality. I drink a decaf, but I’m really attracted to this guy and feeling the tingles and now craving a glass of wine. He must sense this, because he asks if I want to grab a bottle of wine and go to his apartment. Apparently, he’s been sober for a decade and has no issue with other people drinking around him.
7 p.m. We pick up a cold bottle of Prosecco for me and walk to his place. It doesn’t feel like a booty call, per se, since he said his apartment is really cool, and he bought it when Greenpoint was still somewhat affordable (20 years ago — he’s 45), and I’m obsessed with real estate and I want to see it.
8 p.m. Drinking Prosecco in his beautiful garden connected to this cool loft. Jay says he wants to kiss me, so we start making out. Before I know it, he’s going down on me on his bed, which is right next to a fan, and as I close my eyes and feel the fan blowing on my body while he licks me, it’s truly a state of bliss. He puts on a condom and we start to have sex. Excellent sex. His tattoos are sexy and mesmerizing. He smells good. Everything about him is desirable to me.
10 p.m. As I start to dress myself and say good-bye, I am overwhelmed by euphoria. It was such a good night. I don’t know if it’s too good to be true. We haven’t talked about it yet, but I doubt Jay is a marriage-and-babies type of guy. I mean, he’s 45 and single and living the good life as a bachelor. I bite my tongue from asking him about his dating intentions. Instead, I kiss him and Uber myself home to Brooklyn Heights.
DAY FIVE
8 a.m. The first thing I do when I wake up is cancel my date with Max tonight. No way can I hang with a skinny, boring nice guy when a strapping man like Jay exists in the world.
2 p.m. I book a massage for tonight. That will help me stay calm.
4 p.m. I haven’t messaged Jay yet. I hate this dance. The whole: What should my next move be? I am too old for this. I send a quick text. It would be rude not to. I write, “Last night was really fun!! Great meeting you.” I leave it open-ended so he can either ask me out again or not.
6 p.m. I try to relax at my massage. After 60 minutes of heaven, I ask if she can add another half-hour. I just want to drift away for a little.
8 p.m. After I pay and leave the spa, I take out my phone and see that he wrote back! It’s a great text — flirty and warm, and he asks me what I’m doing this weekend! Yay! Now I have to worry about when and how to respond. I hate this. But I love this! I can’t hold back, so I text him that I’m around.
11 p.m. Jay and I have been texting all night. We’ve covered everything from our exes to our parents to our favorite movies and more. I mentioned that I froze my eggs, just to get that out there. He hearted that message. I see that as a good sign, but who knows? I’m horny just texting him. I still haven’t figured out what he’s looking for in terms of love and marriage, but that’s okay.
DAY SIX
8 a.m. I try to see friends on the weekend since I’m always so busy with work and dates during the week.
9 a.m. Spin class with my best friend from college. She’s pregnant, so we agree to sit in the back so she can take it easy. I’m fine with that, since I hate working out.
10:30 a.m. We grab a coffee and talk about the differences in our lives right now. We both agree that we’d love to swap lives, but I think she’s just saying that to make me feel better about myself.
1 p.m. Jay texts me a picture of a loaf of bread that he baked. Did I mention he loves baking? He bakes for his patients. I tell him to save me a piece for tomorrow night, to which he gives a thumbs-up.
6:30 p.m. Dinner with a group of girlfriends. It’s nice to bond with women. I feel jealous of my friends who are married, but I also feel less alone talking with my friends who are deep in the dating weeds like myself. I send a picture of my spicy-cucumber margarita to Jay, and then feel stupid because I had forgotten he’s sober. I feel regretful and nervous about the text, but he quickly hearts it and asks for a picture of me next.
8 p.m. From the restaurant bathroom, I take a selfie. I send it to him.
10 p.m. By the time I get home, we are fully sexting. He wants to know what I want him to do to me tomorrow. I ask him for a dick pic. He sends it. I am practically drooling. We both masturbate to more dirty talk, or at least I do, and text good night. This is so fun.
DAY SEVEN
9 a.m. I couldn’t sleep last night, so I feel a bit groggy today. Thank you, anxiety.
10 a.m. I decide to do a hard-core “me” day so I can get back on track. I take a book to Brooklyn Bridge Park and leave my phone at home. Lots of reading and breathing.
1 p.m. I check my phone; my date with Jay is tomorrow, and he’s texted me three options to choose from. One is a secret sushi restaurant, one is a little outdoor jazz concert, and the other is his apartment for “carbs and other delights.” There is a small flash of negativity inside of me, wondering if this guy is too quirky. He’s edgy and artsy and … I don’t know. Do those types of guys want to settle down and make babies?
4 p.m. I take out a new vibrator that my friend gave me at dinner last night (she works for a sexual-wellness company). Normally, I think about random group sex and other kinky sexual situations when I masturbate. Today, I can only think about fucking Jay. It was so incredibly good. After I come, I text him that I just want to go to his place tomorrow.
8 p.m. I lie in bed with my laptop and do a deep dive on Jay. A few things come up. Pictures of him with model types at parties. That makes me feel both nervous (he dates models?) and reassured (he’s normal enough to get invited to cool things!). I read an article about his work at the hospital in a trade magazine. I’m really impressed by it. And then I read an essay by him that was published on a random blog, and it’s so beautiful and smart and witty that I honestly feel like I could fall in love with this man.
10 p.m. I close my eyes and hope that I can sleep tonight.
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