10 Months of Successful Dating in New York City: A Summary and Analysis

I’ve written the following summary and analysis of 10 months of dating New York City in the hopes that some of you might find it useful. In that time period I dated 32 women and “consummated relations” with 22 of them (~69%). One of my motivations to write this post is that I frequently see advice posted on this subreddit that is at odds with the approach I took, and I would like to provide an example of an alternative approach which I thought was successful.

Because I work in finance and am a piece of shit, I kept an excel sheet with relatively detailed information about each of my dates. This summary is based on a review of that data.

Background

I started the dating period summarized here in my early thirties. After hopping around different industries in my 20s I started working in finance in NYC just as the pandemic hit. My income is in the respectable six figure range, i.e. not enough to buy a multi-million apartment in NYC, but I rent a decent one-bedroom (no roommates) in a desirable neighborhood and have a decent amount of disposable income.

As far as physical measurables, I’m well under 6’ in height and would describe my build as “slightly pudgy.” I haven’t worked out hard much since my college baseball days, but I still retain broader shoulders and decent posture from when I was more active. I come from almost pure Irish stock and so am very pale. I would say that in terms of physical attractiveness I’m average to below-average. I think that this summary may be particularly useful to those of you who feel that your physical characteristics exclude you from the dating pool.

To set the scene, when I began this 10-month dating period I was just exiting a relationship. My goals were a mix between the somewhat incongruous goals of having fun and searching for a long-term romantic partner.

Dating App Strategy

My proactive dating strategy was focused exclusively on dating apps: Tinder, Hinge, Bumble and Coffee Meets Bagel. Occasionally I also went out with women whom I met in “real life.”

I had used dating apps before entering my previous relationship but wouldn’t describe that prior experience as particularly successful. So I decided to adopt a different my approach to (1) my dating profile and (2) my approach.

The following are the three major things I did differently that I believe contributed the most to my dating efficacy.

1. I hired a professional photographer to get pictures for my dating profiles. The session cost several hundred dollars. I ultimately used 3 of the photographer’s photos in my dating profiles (out of 6 total photos).
2. I hired two separate freelancers from fiverr to review all of my photos, including those taken by myself and friends and from the professional photographer, and to advise me on which 6 photos I should use for my dating profile. Both freelancers were women. The freelancers’ services were relatively cheap, in the two-figure range. Interestingly, they had very different opinions from each other on which photos I should use. Ultimately, I relied on the advice of the freelancer who seemed to have a more professional eye (and was less verbose) and used the 6 photos that she recommended.
3. After matching with someone, in over 95% of cases I made no attempt to engage in a text conversation on the dating app. Once I matched with a lady, the first thing I texted was to ask if she'd like to go out for drinks. Not every match responded to my prompts, but a significant percentage did (unfortunately I didn’t keep data on this point). I believe this is the most time efficient way to use the apps. You don’t have time to chat up every match, and the important thing is the number of actual dates you go on, not the number of witty verbal ripostes you have in a text conversation on an app.

Two other things to note. First, I paid for premium subscriptions for all the dating apps. I think this was very important in finding matches and helped me fetch over 200 matches on Tinder within 2-3 weeks of using it. Second, I didn’t list my height on Tinder, which is considered an error by some but Tinder was, for me, the most successful app.

Going on Dates

Planning

I found that if a woman responded positively to my proposal for a date on the app, I would have ~5 days to make definitive plans (time and place) for a date. After that, women would start to lose interest and tend not to respond to follow-ups regarding actual plans.

Almost all my first dates occurred at one of three bars/restaurants in or within walking distance of the Manhattan neighborhood of Greenwich Village, where I live. Women did not seem to mind dating in this rather trendy area, as dates commuted as much as 1.25 hours for our date (two women did this, one living on Long Island and another in New Jersey). Sometimes I’ll hear my female friends state that they find amiss men who plan first dates so conveniently close to their apartments. In New York City, at least, I recommend you ignore this complaint and plan your dates conveniently near you.

Conduct During Dates

For conversations, I felt that my age was an advantage versus my experiences in my 20s. I had a lot more to talk about and could carry conversations with women much more easily. The only things I kept in mind in terms of communication was to make eye contact during conversation and to refrain from talking about baseball. I sometimes breached the latter rule and would notice my date’s eyes glaze over with boredom before I corrected myself.

I never mentioned sex during the first date and would advise you to refrain from the same.

First dates could go several different ways. During some, my date and I would swelter amidst smoldering chemistry and only linger at the bar for under an hour, perhaps two drinks, before returning to my apartment. Other dates would span several hours and two or three locations, perhaps ending with a return to my place, or perhaps not.

I found it easy to come up with excuses to go to back to my place at the end of the night. “I have a nice rooftop, want to come drink whiskey / smoke cigars / look at the skyline with me?” I have a nice whiskey collection in addition to a well-appointed bar which includes mixology tools. Sometimes the date would mention a cocktail or whiskey she liked and I would offer to give her or make her something similar at my place. My recommendation from these experiences is that if the date is going well and the lady feels comfortable with you, you don’t need a grand excuse or really good reason to persuade her to go back to your place. But whatever you do, don’t explicitly mention sex!

At My Place

The majority of my first dates (~66%) returned with me to my apartment. This is not to say that intercourse ensued every time I brought a date back to my place on the first date (that rate is 71%).

Many claim that you don’t need money to successfully attract women. They’re right! But what is also true is that having money and nice things helps a lot. The reason I make this point is that my apartment played an important role in the courting process.

Your date’s initial impressions of your home are important! The home reflects the man and once you introduce a date to your place, they’ll form several judgments about you based upon how you crafted your living environment.

I recommend investing money and time making your home appealing not only to yourself but also to guests (including your potential dates). An example: while one of my walls was covered in Red Sox-related prints and memorabilia (generally appeals only to men or fellow Massholes), another wall showcases a small collection of Norbertine Bresslern-Roth prints (generally appeals more to women). I have nice leather furniture and a breakfast table where I can entertain guests over drinks and card games. And, of course, I always spruced my place up before a first date. I’ve noticed that these things, among others, made favorable and important impressions upon my female guests.

Once at home I’d typically make some cocktails (I’d choose which base on my earlier conversations with my date), play some soft music from my Bluetooth speaker, break out a deck of cards and play (or teach) gin rummy with my date either on the rooftop or at my breakfast table. I recommend playing some kind of game with your date rather than simply turning on the TV and “chilling”, though I did do the latter occasionally.

I found that the transition from gin rummy to the bedroom occurs rather smoothly. Playing gin rummy offered many opportunities for flirting or light touching. After making out a bit on my couch, I would carry my date to the bedroom—I never encountered a single woman who didn’t like being carried, and if you are too weak to do so then you should go to the gym and work out until you can.

Results

In a 10-month time period I went on dates with 32 women and “consummated relations” with 22 of them (~69% of the total). 19% of my dates were one night stands, and 50% became repeat encounters.

The average and median age of my dates, consummated and unconsummated, was 26. The youngest was 20 and the oldest was 31.

The median date consummated relations with me on the first date, but the average number of dates it took to consummate was around 1.85. Excluding women who consummated on the first date, the average dates it took to consummate was 3.

I made some nice graphs to elucidate the comments below but unfortunately this subreddit appears to have disabled posting images.

Comparison of Apps

Tinder was the most successful app in terms of “consummation” by numbers, resulting in 10 consummations out of 14 women dated. Coffee Mates Bagel was the least successful, resulting in 1 consummation out of 2 women dated. A few months into the 10-month period I stopped using both CMB and Bumble because I wasn’t getting as many quality matches on either of those as I was on Tinder and Hinge.

Ethnicity

The graph I made but which I can't post is more insightful than the following text description. I graphed what percentage of women consummated relations with me by ethnicity. I divided white women into three separate categories: into those of Eastern European descent, Jewish women, and white women who did not fit into either of those two aforementioned categories. The highest percentages belong to Eastern European women, Jewish women and East Asian women, in that order.

I think the main thing the graph showed was to affirm my prior bias that Eastern European and Jewish women are comparatively more likely to put out in New York City. As another confirmatory piece of information, Eastern European and Jewish women also had the lowest average number of dates required for consummation (1.25 and 1.66, respectively).

Performance Over Time

To assess whether I became “better” at dating as time went on, I charted the average number of dates until consummation, per month, as a proxy variable for my “dating skill”.

Interestingly, the average increased from month 1 to month 3 (a max of 4), but from the fourth month on, if I had relations with a date, it would always occur on the first date. I think there are two plausible mechanisms for this shift: (1) I was more attractive and persuasive during the dates themselves, or (2) I was better at selecting women who would “put out” on the first date.

I think the graph does capture that simple point: if you spend time dating, you’ll gradually become better at dating, whether by becoming better at selecting and filtering dates or by becoming better at the dates themselves.

On Daygame

In perusing this subreddit I notice that a lot of attention and advice to males seems to given to what is often called “Daygame,” which seems to be based on cold approaching women in the street. Online dating was successful enough for me so that I never felt any desire to try my hand at this, but I thought I might share an anecdote I found insightful from one of my dates.

The setting: a Friday night at one of the bars I usually go to for dates in Greenwich Village. My date, a voluptuous 25-year old Eastern European women, is a few minutes late. After introductions, she talks about a funny experience she had on the way to the bar.

“Some guy stopped me while I was walking on my way here on [redacted] street. He told me that I ‘look like a ninja’ because of all the black I'm wearing and asked if I thought I was a ‘rebel.’ This dude was not cute but kept talking to me. Eventually I had enough and was like, ‘sorry, I’m on way to a date.’ He asked for my number and I ignored him.”

In a few hours that date and I would become physically intimate, while the guy approaching women in the street likely spent the night alone. Well, maybe he got someone else’s number if we’re optimistic.

My point with this story is that the advantage of dating through apps is that it’s time efficient. My time with women was spent on dates instead of cold approaching them in the street. If you’re considering investing time in daygame, please first consider whether it is an efficient use of your precious time versus the alternative of online dating.

Managing the Stable

If you’re dating multiple women successfully, perhaps by using some of the advice within this post, you’ll quickly find yourself managing a stable of mares, so to speak.

I do not think my approach to managing the stable was optimal. Unless it’s a one night stand, once you become physically intimate with a women the amount of attention they expect increases with time. Managing to keep multiple women physically interested in you at once requires a significant expenditure of your most valuable resource: time. You have to give each “mare” enough dates and time to keep them from moving on from you. For some, a week of not seeing you is enough to end their relationship with you.

My job, which often requires very late hours, provided an unexpected benefit in offering an excuse to women as to why I hadn’t been on a date with them recently. Often my dates would fall asleep in my bed around midnight, while I would continue working on my computer in the living room for a few hours more. Since they knew I was very busy, they were inclined to write off my lack of attention as due to work.

I don’t think I was able to keep more than five or six women open to intimacy with me at the same time. Generally, I noticed that younger women (≤ 24 years) tended not to have the same expectations of attention as women ≥ 25 years in age. If you are dating just to have a good time, then I recommend skewing a bit younger, as it will make “managing the stable” significantly easier.

Recommendations

My recommendations based on my experience are below. Please feel free to comment on whether you disagree with them or not.

1. Move to New York City. This recommendation wasn’t really discussed above, but the dating market here favors men to a ridiculous degree. I’m sure that I would not have been as successful in another metro area.
2. Invest resources into dating. Whether it’s spending money on photos for your apps or making your apartment look nice, I feel that spending your money intelligently to make you more attractive to dates offers a very high return on investment, so to speak.
3. Don’t spend time chatting on the apps or on other inefficient activities. Your time is best spent on actual dates. Be straightforward and message matches soon after you are matched and simply ask them out. You’ll be surprised by how many respond with “I’d love to!”