July 12, 2024

Brad Marolf

Business & Finance Wonders

The Woman in Finance Going on a ‘Dating Binge’

The Woman in Finance Going on a ‘Dating Binge’

Photo-Illustration: James Gallagher

This week, a woman who goes on a new date almost every night while applying for a big new job in finance: 35, single, Brooklyn.


9 a.m. Wake up, masturbate. I was a late bloomer when it comes to sex in the sense that I feel like I’ve only just started discovering my sexuality. I had never really masturbated until five years ago when I started a very stressful job in finance; it became one of my biggest sources of stress relief since it’s fast, deeply satisfying, and portable. My horniness has been out of control recently, so I’ve been masturbating a lot more as I’ve simultaneously dipped my toe back into the dating pool.

10:30 a.m. Go to the gym. My relationship with my body is a huge part of this recent progression in my sensuality. I’ve been feeling better about my body than ever; much of that is from going to the gym and feeling powerful and accomplished.

12 p.m. It’s been a rough few years as many, many friends have gotten married and started having kids. Finding a partner and starting a family is something I really want, and it’s been frustrating to watch everyone else move forward while I’m stuck in place. In the last two weeks, both of my closest friends and my brother told me they were pregnant. I’m happy for them but definitely caught off guard. I told myself I would take this weekend to let myself cry, grieve, feel sorry for myself, and journal, so I spend a couple hours doing it today.

4 p.m. Bumble strategy? Swipe yes on every guy, send them all the same message, and then filter whoever replies. High volume, baby!

8 p.m. A texts about coming over. We went on a first date about a week ago, and it ended with some very hot making out. He’s into smoking weed, which I can get behind. I can’t hang out tonight, as I have a job interview in the morning and want to be really fresh for it, but I’m happy to hear from him.

10:30 p.m. Masturbate. Sleep poorly anyway.


7 a.m. When I wake up, I have a text from J saying that he is back from vacation and wants to see me tonight. We went out a couple weeks ago and just haven’t been able to make our schedules work for the second date. We didn’t even kiss, but I sense that he’s a little freaky, and some of his texts have been adorably suggestive. I reply and confirm for after-dinner drinks.

10:30 a.m. As I’m getting ready for the job interview, I decide to text A a pic of my ass. He loves it. Makes a sly suggestion about coming over to my apartment for “lunch.”

12:15 p.m. Job interview goes well, I think. Feeling confident.

1 p.m. Go out to grab lunch and A texts me; he was serious about a nooner. I’ve never done that before, but since I work from home and he can come over pretty quickly during his lunch break, I acquiesce. I run home to clean the apartment and change into the thong I sent him a pic of.

1:30 p.m. A comes over. We start making out. We both want to fuck each other pretty badly and start taking each other’s clothes off. He bites my ass hard. Just before he’s about to enter, he stops and asks to smoke a joint. I can’t right now — have a presentation later and need to have a clear head — so I tell him I don’t have time. We keep going, but he stops after a few minutes and says he doesn’t want to continue. I’m bummed, but I totally get it — it’s hard to get the mood just right in the middle of the day, and this is a weird way to have sex for the first time. He leaves, and I go back to work.

5 p.m. After a slew of meetings, I text J to find out where he wants to go for drinks. I shave my legs while I wait for his reply.

6:30 p.m. Dinner with a few friends, including one of the pregnant ones. We chat about the baby, but it doesn’t dominate the conversation, which is a relief.

8:15 p.m. I run across town to meet J for a drink at a dive bar near where he lives. We chat at the bar, and I try to play footsie, but he isn’t really responding to it. We are having a more intellectual discussion, which is enjoyable enough, so I let it alone. I figure that if he wants to hook up, he will initiate.

11:30 p.m. While we’re having our last drink, he reaches across the table to grab my hand. Where was this touch two hours ago? I’m exhausted and no longer feeling the vibe between us, so I suggest we leave. Outside, he casually mentions that he is going back to his home country tomorrow, in Europe! He grabs my hands and kisses me, so we end up making out a little before I hop in a cab. I text him on the way home that I had assumed we were going to have sex, but I wasn’t sure if he was interested. He said he was trying not to be pushy since he had heard that American girls are sensitive to come-ons. Fair point. But damn — what a missed opportunity. We promise to stay in touch if and when he comes back into town, though I’m not sure if I’ll follow through.


7 a.m. Have a long day at work and another date tonight with Z, so need to find some energy from somewhere. My first date with Z was fun and ended up with some nice making out on a street corner, and he invited me over to cook at his place for the second date. I’m feeling more confident about the chemistry and physical direction of this one, so I’m looking forward to it. I do notice that one of my boobs has a little bruise-slash-bite mark from A yesterday — hope Z doesn’t notice!

9:50 a.m. Send A a text to check in after his swift exit yesterday. We’ve only hung out twice, so if he’s not feeling it anymore, it’s not a big deal, but I liked his vibe and would love to explore it.

11 a.m. Weekly therapist appointment. She is broadly supportive of my dating strategy but cautions me that I’ve gotten burned-out quickly before when on a “dating binge” and to be extra cognizant of my feelings right now given the multiple pregnancies and my anxiety about it. I miraculously don’t cry.

6 p.m. Get ready for date with Z. There is definitely a mark-slash-bruise forming on my boob from A, so I need to wear something that doesn’t really show cleavage but is still sexy. I go with my “fuck me” dress, which is crewneck, long-sleeved, has a long skirt with a high slit, and clings to my curves.

7 p.m. Head off to Z’s house for our date. We spend about an hour chatting while cooking. The moment that the forks are down on the plates, we start making out on the couch. We move to his bedroom and proceed to have some of the best sex I’ve had since before the pandemic. We have excellent chemistry, he is very open and experimental but not pushy, and even our pillow talk is good. We both come multiple times.

11 p.m. I grab a cab and head home. The ride is pretty bumpy, and I’m still turned on, so I masturbate quickly when I climb into bed, because why not.


 9 a.m. I sleep in and didn’t masturbate this morning. Gotta give my pussy a break.

12 p.m. Lunch time.

3 p.m. I ordered $300 worth of lingerie online last week, and it arrived yesterday. The sizing is all over the place, but at least this company has lots of options for the curvier ladies among us. Most of it doesn’t fit quite right, but there are a few things I’ll keep or exchange, including a crotchless thong that I surprisingly like. I snap some pics to have on hand later.

6:27 p.m. After running errands and grabbing dinner, I spend some time on Bumble, messaging some of the guys who have replied from a few days ago (real range of filthy to sweet to weird) and matching with new people.

9:30 p.m. Pop a sleeping pill and pass out. Well deserved sleep, finally!


3:30 a.m. Sleeping pill has apparently worn off. While I was out cold, B texted me asking for a selfie. B and I dated briefly just before the pandemic when I was living on the West Coast. The sex was incredible, and he seemed to really like me, but once lockdown started, he was completely unavailable and unresponsive. He’s reached out a few times over the last year to keep the horniness alive. I send him two of the lingerie pictures and ask for his opinion.

2:33 p.m. New guy from Bumble, H, texts to say he might be able to make a drink tonight work instead of midday Saturday, which is infinitely more appealing.

3 p.m. The head person at the job that I interviewed for earlier in the week wants to grab lunch tomorrow. This is generally a good sign in finance, but without a clear job offer, it’s a bit of a mixed message. I rearrange my schedule and plan to wear something nice. Hope it’s a job offer but prepared for general networking or “better luck next time.”

5 p.m. A has unmatched me on Bumble. Absolutely for the best, but it never feels good to be the one rejected.

8 p.m. Meet up with H for a first date. My suggestion was to meet at my favorite local bar, which is just two blocks from my place. I wear the “fuck me” dress again because this boob bruise is getting worse. He turns out to be a nice guy, and we chat very easily. He has a frenetic energy that I’m digging — I’m always happy when I’m not having to carry the conversation on a date. We make out a bit at the bar — I feel a little bad for the bartender as it’s happening right in front of him, but hope he enjoys the show.

9:30 p.m. After two drinks, H suggests we leave. We’ve been kissing and caressing each other, and I am incredibly horny from all the messages B sent me today. I invite him up to my apartment for a drink in hopes that my “fuck me” dress will keep its streak going. It works. He asks to turn out the lights while we are making out on the couch, so I get lucky that he won’t see the bruise. His modesty is actually really cute. We move to the bedroom, and in the dark, I can see his over-whitened veneers light up with a huge smile while I ride him. I don’t usually like being on top, but it feels amazing with him. When we have gone through two condoms, I’ve come so much that my bedsheets are soaked.

11 p.m. After H leaves, I change the sheets while texting B, who is awake on the West Coast and wants to FaceTime. I can’t tonight because the big lunch for the job interview is tomorrow.


7 a.m. Wake up to a text from B after I fell asleep sharing the porn he watched last night.

12:30 p.m. Big lunch turns out to be a final “get to know you” interview for this job. Enjoyable but stressful. Glad I relieved some stress last night.

3:30 p.m. H asks to hang out again. I love a man with a good follow-up game. I’m booked up this weekend and heading out of town for work next week, but I promise to ping him when I’m back.

7 p.m. Out to dinner with my best married couple friends (of recent pregnancy fame). I catch them up on my dating exploits, and the husband and I drink some wine.

11 p.m. Texting B on the way home. He wants to FaceTime in 30 minutes. I am kinda drunk, so I agree and quickly get ready for bed in some of my sexier pajamas. I masturbate while I wait for him to call.

12 a.m. Text to B that I am at risk of falling asleep, as he seems to be running late. Give him 15 more minutes. Plug in my phone and go to sleep.


8 a.m. Wake up to a few missed FaceTime calls from B. He apologizes for being late. This aligns with my recollection from when we were dating — he talks a big game but then somehow we always end up like two ships in the night, missing each other.

2 p.m. Prep for grabbing drinks with some friends and my date with Z. The boob bruise persists, so I decide to wear my more conservative first-date outfit of a long skirt and soft sweater. Shave my legs and lotion up — both H and Z complimented my soft skin, so I gotta stick with it.

5 p.m. Meet up with some friends for a drink or two. Another friend announces her pregnancy! If I didn’t have a date lined up for tonight, I might be more upset by it, but I’m quite happy for her.

8 p.m. Head over to Z’s for takeout. The food is fine, and we make out for a bit. A little less foreplay, but the sex is even better. Again, multiple orgasms for both of us, and I’ve again soaked the sheets — at least they aren’t mine this time. I leave around 2 a.m. to head back to my place.

3 a.m. I go to bed finally feeling sexually satiated for the first time all week. Maybe I can take a break from masturbating.

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