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This week, a 30-year-old man starting to look for something more serious: single, straight, Tribeca.
10:55 a.m. I guess the first thing you need to know about me is that sometimes I drink too much. And the second thing is that I like to sleep late. Clearly, these facts are tied to each other but I’m not especially interested in changing either at this point.
10:57 a.m. The third thing to know is that my mother lives in an apartment below mine. We own the building, which might sound pretentious but it’s really not. I’m the child of immigrants who were very smart, and extremely lucky, in buying a building in Tribeca about 30 years ago, just when I was born. We are cash poor but this building keeps us all feeling financially secure, despite a lot of other ups and downs. There are a few tenants and me, and my mom (she and my dad divorced years ago and he lives in Florida now).
11 a.m. Oh — and there’s someone in my bed, Jenna. She and I met on Tinder about a month ago, and she’s one of three women I’m dating right now. Quite frankly, I like all of them, and I’d happily become exclusive and monogamous with any of them … but I’m not sure if any have strong feelings for me. I’m very insecure with women.
I think I’m an average lover at best, and I’m not particularly tall or attractive. I have a good heart and a decent personality, and all the girls swoon over the fact that my family owns this building so I milk that pretty hard.
11:05 a.m. Jenna is waking up. She parties hard. I think she did blow last night and then took some kind of pill to sleep. We didn’t have sex — we kind of both just passed out in bed. I don’t do drugs so I’m a little naive as to how her night really played out. We met up at a party — her friends, not mine. I drank. She bopped around. Then we went back to my place, kissed a little and passed out.
Noon Jenna and I are getting Italian heroes in my neighborhood. She never seems to eat much but when she eats, SHE EATS. This morning she’s wolfing down her sandwich like it’s the last sandwich on Earth. As we walk away, I look out for my mother who is always lurking around. She’s the neighborhood’s busybody. I don’t need to explain this girl to her, since she met another one just yesterday. Yikes!
2 p.m. Finally, I get to work. I have a small events-planning business. I work with a few corporate clients with big budgets and low creativity. They all think I’m a fucking genius.
8 p.m. I’m doing work emails and running around to meetings until late. Meanwhile, I’m checking in with all the ladies. None of them seem particularly stoked to hang out with me.
I find that if I make it about taking them out to dinner, they respond more positively. I always splurge for really, really nice restaurants (wherever they want to go). But I’m too tired for a big song and dance tonight. Nothing it is, then.
9 p.m. Grab three slices of pizza and go home to crash.
9:30 a.m. Oh sweet sleep, I love you so.
10 a.m. I jerk off in the shower. What man doesn’t? I try not to jerk off if I know I’m seeing someone special later, but as of now, I don’t have plans. Sometimes I have a hard time getting it up if I’ve been drinking … whiskey dick, as they say. I’m self conscious about it, but hope for the best.
3 p.m. I had a long work day. Jenna texts to see what I’m up to later, if I want to Netflix and chill. I’m annoyed that I beat off already. But I tell her that works.
8 p.m. Jenna comes over in her pajamas. It’s cute! I make us Negronis and we cuddle up on the couch. We can’t find anything good to watch.
9:30 p.m. We gave up on finding a great movie and instead I go down on her for what feels like 45 minutes in my bed. I want to make her come. I have studied very, very, very hard on the art of oral sex. Personally, I’m not obsessed with getting blow jobs — I think it’s because I’m insecure about my average-size penis and not just because it has an erection issue. Eventually, she comes, and I’m pretty psyched about that.
10:30 p.m. Jenna leaves. In the few hours she was at my house, my two other ladies texted. They’re both at separate parties and I believe both drunk texted me — basically, like “heyyyyy” and “whatchaupto!” I’m ready for more than hey and watchupto. I’d like a girlfriend.
Midnight Feeling depressed, I fall asleep with a third Negroni next to my bed.
10 a.m. I deliberately do not masturbate in the shower.
1 p.m. At work meetings. I’m a one-man show but I’ve had to hire a few assistants for one particularly large event I’m in charge of. I take everyone to lunch to talk about the division of responsibilities. One of the assistants I hired is beautiful and I know for a fact single, but I’m extremely professional.
3:30 p.m. I stop by my mother’s apartment after my lunch. She’s such a riot. She wants details on my dating life, as always, and puts the pressure on for grandchildren. I indulge her a little bit and tell her I’m feeling ready for something serious myself. I can tell this confession makes her really, really fucking happy.
5 p.m. I’ve decided of the three women I’m dating, the one who is the most stable and promising is Simone. She does go out a lot, though. She’s in PR, so I suppose that’s a professional hazard.
The only serious girlfriend I ever had was in PR too — she and I dated her for about three years. Her family loved me. But she cheated on me with an investment banker. What a cliché. I was willing to take her back despite all of that, but she had fallen in love with him. This was three years ago and from what I hear, they got together, he cheated on her multiple times, and now she’s alone.
Anyway, I make a calculated effort to write Simone a nice text inviting her to dinner, trying to make it sound a little more serious. A little less casual. “Let’s go somewhere romantic,” I write.
8 p.m. Crickets.
10 p.m. Crickets.
11:30 p.m. She writes back, “I was at an event sorry. Good night!” Um. Okay?
10 a.m. Therapy! The timing couldn’t be better. We always talk about my insecurities but today I come to her with the revelation that I want someone serious but clearly I’m looking in all the wrong places. I seriously need a dating coach more than a therapist. She gives me the “you gotta love yourself first” crap … and I know she’s right … but don’t tell me everyone out there in a healthy relationship totally loved themselves first. Did they?? All of them?
3 p.m. I worked from home all day and now want to nap. Good night.
8 p.m. I woke up unsure if it’s 8 in the morning or eight at night. Weird! When I realize it’s nighttime, I scramble to make plans. I’m energized. I pour a nice red wine for myself as I text around to see what’s going on.
9 p.m. My two closest friends are hanging with their girlfriends. I text all three of my ladies and no one appears to be available. A week ago, I deleted Tinder from my phone because I felt like I was over capacity but I decide to log back on.
11:30 p.m. I’ve finished a bottle of wine by myself and am chatting with about six new women. A few excite me but it’s probably better to revisit these conversations in the morning … good night.
10:30 a.m. I wake up feeling dirty.
12:30 p.m. My mom has made my favorite meal so I go there for lunch. I feel guilty that I have no positive life updates for her. I know that’s what’s she’s waiting to hear from me. What do I say, that none of the women I’m dating are seriously interested in me? I tell my mom the truth about most things, but some things she doesn’t need to know.
6 p.m. I did work in a mild state of depression all day. I don’t log back onto Tinder. I think it depresses me more than lifts me up.
8 p.m. Sushi dinner with my best guy friend. We grew up together here in the city, and he knows and gets all my quirks. I tell him that I really want a girlfriend but I don’t know what I’m doing wrong and why I’m striking out with everyone. He says it’s because I’m obviously dating the wrong girls. I think what he means to say is that I need to stop chasing beautiful women and date — what? — unattractive women? I mean, I’m all for dating “within my league,” but I’m not that bad!! More than one person have told me I resemble Andrew Garfield — and he dated Emma Stone!
10:30 p.m. My friend and I have a great time out together. I love this guy. He’s really lucky that he met a great girl in college and they’re really happy. I love her for him. I guess compared to the women I date, she is a little more “basic,” but I think I’m turning a corner where basic isn’t so bad.
11:30 p.m. I jerk off thinking of Emma Stone.
9:30 a.m. Saturday is the only day I work out. I’m in a running club and we meet on Saturdays. Somehow I’m a decent runner despite never hitting the gym or running on other days of the week. It’s a mix of men and women. Again, I try to be super appropriate and not flirt or really even look at the women.
12 p.m. I do another weird thing on Saturdays. I go to a church group. My family comes from a very Catholic country — my parents were never very religious though. I’m enjoying learning about my religion in this group though. I started going to it when my ex-girlfriend cheated on me and I saw a posting about the group on Facebook. It’s just like talking, and some Bible studies but not in a lame way. There is a really nice, pretty girl here on some weeks, but not today. I think I’m going to ask her out next time she’s here. I could find her on Facebook — we’re all in the same group — but it might seem creepy. I spend most of the session here thinking about that girl and how fateful and “blessed” our story could be …
6:30 p.m. Dinner with my mom. She knows the way to my heart. I tell her I stopped seeing all the women I was seeing (a white lie, really they’ve all stopped texting me back) and that it’s a fresh start. I love my mom and honestly don’t want to end our dinner. We’re both alone, but at least we have each other.
8:30 p.m. We decide to take a walk around the neighborhood and stop by a delicious ice cream shop. Then I call it a night.
10 a.m. Well, not that much sex this week. I’ve often suggested to my therapist that my libido is lower than average. I don’t crave sex the way I crave love. I’m not driven by sex. Life might be easier if I were?
12 p.m. I grab a very large coffee and log back into Tinder. I have like 20 messages to respond to. One by one, I go through the women I’ve matched with. I eliminate the ones here just for the weekend. I eliminate the ones who literally write, “do you like to party?” I’m left with about five potentials, and I decide to be very open with all of them. “Are you looking for something serious or just a fling? There’s no right answer …” I kind of hold my breath as they write back throughout the afternoon. Four write back versions of: “I guess something serious.”
3:30 p.m. Jenna and Simone both text as I engage with these new women. Wouldn’t ya know it. I ignore them. I’m very busy setting up dates for the upcoming week.
6 p.m. I go down to visit my mom and eat some leftovers. And because I’m the best son in the world, I let her scroll through my Tinder and pick out some women she thinks look good enough for me. It might be the happiest moment of her life.
10 p.m. No more dates with partying women only interested in nice dinners and my apartment. No more pretty but empty women for me. Tomorrow is going to be a fresh start.
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