The Infinite Pussy Glitch, Pt 3: Dating as a 50-Something NYC Man
What happens when a hedge fund CEO runs his love life like an optimized sales/marketing funnel?
Mark1 reached out to me after reading my first Infinite Pussy Glitch article about a 30-something NYC man. He said he had his own data set.
I assumed he’d be another 50-something guy with a vaguely inflated sense of his own market value. Instead, I found someone unusually self-aware, meticulous, and quietly effective — the kind of man who runs his dating life like a sales funnel and keeps a running spreadsheet of match rates, rose ROI, and prompt performance.
Over the past several years, post-divorce, Mark has been on over 100 first dates. He’s had some success, some flops, and a full aesthetic overhaul. This is not a story about a man who gets women because he’s rich. It’s a story about what happens when you treat online dating the way you’d treat performance marketing — and how a handful of optimizations can take you from merely mid to in demand.
Why He’s Successful
While I found his strategy for matching with the most attractive women on Hinge fascinating (something we’ll call “spearfishing”; we will get into the nitty gritty later on), his real gains came from improving his profile and more importantly, his appearance.
In my career, I manage paid ads for ecommerce. One professional shower thought I’ve had is that all the cheap clicks and great ads in the world don’t matter if you’re trying to sell a product no one wants. In dating, as in ads, conversion is king.2
Similarly, with dating, using the best apps, perfecting your messaging strategy, and paying for the most expensive tiers of dating apps matters 0% if the profile is unappealing. For that matter, it’s awfully tough too if no one wants to go on a second date with you after the first should your profile not match reality.
There’s an unfortunate winner-takes-most phenomenon in online dating where some 2017 Hinge data revealed that the entire bottom 50% of men get 4.3% of all the likes vs the top 10% who get 58%.3
It’s not great for women either: the top 10% of women get 45.7% of the likes and the bottom 50% get 7.9%.
There’s some kind of math lesson in this, akin to the “haha gotcha!” moments when you model compound interest on retirement accounts. Marginal improvements on your profile have outsize returns: making it 20% better should improve/increase your matches by more than 20%.
If you’re going to take away anything from this article to improve your own dating success, it’s that you should 1) Focus on improving your profile and more importantly, 2) Focus on improving yourself.
He showed me his first set of Hinge photos that he started with and they were hilariously less good.
Before: pleasant-looking, middle-aged man in glasses and slight paunch. I would describe the energy as “unthreatening.”
After: handsome, silver fox George Clooney aesthetic. A “zaddy”, as the kids would say.
When I initially googled him, I kept zooming into old photos online and comparing the eye and ear placement to make sure I had found the same person because I was so taken aback.
Ultimately, Mark’s objective with all this data optimization is to find a true life partner. He doesn’t think or talk about it on dates.
Dating Apps and Paid Features
Mark is not shy about paying for dating apps.
What I find interesting about the above and below charts is that you can see how he’s responded to the vastly different user dynamics and monetization strategies for each of the apps.4
The breakdown is like this:
Bumble: Relies on inbound - attractive women come to him
Hinge: Sends Roses to Standouts - attractive women are often hidden
The League: Sends Power Moves - gets visibility in the limited # of prospects shown to desired women
Bumble, he notes, has excellent inbound. There’s a faster nature of the app and the higher number of swipes per day for free users. I would guess that this means they don’t gatekeep attractive users from each other as much.5
His League plan includes unlimited “Power Moves” (making sure you’re visible in the next batch of 3 prospects). He sends almost exclusively roses on Hinge but doesn’t buy extra SuperSwipes on Bumble, just using the ones that come with his subscription.
While it’s hard to generalize from one man’s data, it suggests that even if you’re an attractive man, if you want to be seen by the most attractive users on Hinge and The League, you have to pay up. Bumble should have less of a visibility issue.
There are little algorithmic tricks6 to at least temporarily increasing the attractiveness of your regular stack on Hinge.
Hinge Data and Strategy
Here’s an infographic with fun facts from his dataset!
Studies have shown that women find men around their own age most attractive and a chart with the age of inbound likes bears that out: he gets the most interest from women in their early 50’s.
His regular like match rate is higher than with roses because he sends roses far more selectively and almost entirely to women in his Standouts section (who are more popular).
Over 60% of women match within a day of receiving a like (I cut out 8+ days because the tail got way too long).
He has a good conversion rate (as far as online dating goes) from first to second date, at 36%.
Spearfishing: Targeted, High Effort Outreach
In one academic paper I read, the researchers noted that there were 2 different strategies for online daters: those who tried to match with anyone, and those that chose fewer, more desirable targets.
Over time, Mark ditched the spray-and-pray strategy. He upgraded to HingeX and now almost exclusively sends Roses to women in his Standouts.
His funnel math?
21% convert to matches
77% reply
30% go on dates
At $1.49 a Rose, that’s ~$31 per date. But every message is tailored, every move deliberate. It works.
I don’t recommend this strategy unless you’re already having good success with regular likes. You will waste your money.
Biggest Profile Boosts
Mark has seen much better results in the past 6 months than he did initially thanks to a few major optimizations:
Job title (specifics behind paywall for privacy)
Better photos
An AI-generated shot in an urban setting (his best performing on both Bumble and Hinge) - anonymized version and the AI service he used behind the paywall to protect his privacy
Two activity shots of him doing his favorite outdoors activities
One with his son
One with friends
I also give some anonymized versions of his prompts behind the paywall as well.
My Reflections
I now know this man really well. We struck up a friendship 2 months ago and we trade dating missives on a practically daily basis. I have heard his thoughts, mundane and profound, on a lot of topics and what I’ve noticed is that Mark’s success with dating is really a function of the following traits:
Conscientiousness. He works hard. He puts in the reps. He treats dating like he’s an ambitious junior analyst getting constant critical feedback from his boss.
This quality also comes out in his appearance: he works out a lot, lost a bunch of weight after his divorce, and experimented with his style/grooming to figure out what look worked best for him.
He’s naturally disciplined, detail oriented, and data driven - I think he just enjoys the process of understanding and solving problems and continually improving. He finds this engaging, not frustrating.
Doesn’t personalize failure: he gets a bunch of rejections but is careful not to take it too personally and uses it as feedback for how to do better.
It is super clear to me that the qualities that have made him a successful CEO are exactly the same qualities that make him good at online dating. It’s ultimately a lot of common sense stuff, but the kind of person that approaches problems this way is also the kind of person that is motivated, tries stuff, and does more of what works and less of what doesn’t. Where people often get stuck is that they don’t like the results from online dating and blame stuff outside their control rather than focusing on what they can control.7
Initially, I was wary that he might be a bit sleazy, but he really does his best to be quite ethical in his approach, despite going on a mind boggling amount of dates with beautiful women. I suggested he put up a picture of him with a cute dog and he refused because he thought it would be false advertising. He avoids sleeping with women if he senses they like him a lot but he knows he isn’t interested in dating them long term.
He also does things that are a bit bare minimum for gaining my respect, but are worth noting anyway: He doesn’t set his sights on 20-somethings. He doesn’t lie about his age. He looks like his pictures.
About the Desirability of Men as they Age
I think I fundamentally misunderstood what was meant by men accruing desirability with age.
I always thought - correctly! - that young women didn’t want men in their 50s and 60s. That is why so many men lie about their age on dating apps. Emotionally healthy, not financially desperate 20-something women are usually not attracted to men their father’s age. It just feels weird.
However, what I failed to account for is the vast churning tides of demographic shift that come with age.
After 40, the numbers rapidly become brutal.
Men just… die.
They get married and stay married. Or they die. The ones left often don’t look very good.
If you are single, decent looking, have a full head of hair, well-mannered, and successful - actually, just 3 out of 5 will suffice - you’ll be at an absolute unfair advantage for a pool of women in their 40s and 50s that are, in absolute terms, far more beautiful than the *average* women in their 20s, in the way that JLo is undeniably hotter than your average 25 year old.8
Youth has its own dewy sheen that no scalpel, needle, or exercise routine can replicate. But raw beauty, the kind that features supermodel bone structure and taut abs, lives on.
In my month of friendship with Mark, I was boggled with the beauty of these women. They were stunning and would rank 7-10 on the attractiveness scale of all but the most age-for-age’s-sake grader. For the purposes of this discussion, I’m not even going to mention careers, because men only sort of care every sometimes about that stuff. For Mark’s purpose, he mostly cares they are intellectually engaging; someone having an impressive career is a definitely plus, though. (I would say his unicorn woman is a 40-something blonde former model who’s also a CEO and loves outdoor sports. Reach out to me and I’ll put you in touch if that sounds like you.)
His Profile Pictures, Job Title, Prompts, and Advice
His profile really is the key to what drove his success. Here’s the photos (including the surprising AI-generated one that outperformed all his real ones!) as well as what service he used to create his AI headshot. See the exact job title tweak he made that improved his match rate. I also included some words direct from the subject himself on how to date successfully.