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Problem number one, that girl in the opening picture has a ring on her left hand. Perhaps try again with single girls?
Is it unethical to go out with someone that wants out of their marriage? A divorce is costly, takes a lot of time, and the relationship is usually dead long before the papers are finalized.

If there's trickery involved, then sure. But it's not quite so clear-cut. Where it gets murky is if you don't have a job, you're stuck -- it's very difficult to leave your marriage without at least attempting to find someone else before a divorce. But the alternative is to be a slave to your partner's whims, if the marriage is sufficiently toxic and unsalvageable.

Regardless of the ethics, it's probably just not going to work out...
Even in that case, why wear the ring in the picture? Edit: On second look, that picture looks to be a stock photo, not one of the dates the author went on.
Sure, if the relationship has reached that point, she probably wouldn't be wearing a ring. I'm just curious what everyone thinks.
I think this is probably a stock photo just used to add a photo to the article.
Is nobody wearing rings just for fun?
I've certainly met people who wear rings specifically to suggest they're unavailable, or at least cut down on the number of propositions.
If there's not trickery involved then they wouldn't be wearing a ring, surely?
Yes, it is still unethical.

> Where it gets murky is if you don't have a job, you're stuck -- it's very difficult to leave your marriage without at least attempting to find someone else before a divorce.

Are you saying that you should continue to live off of the spouse's salary while shopping on the side?

It's easy to turn this question around: Are you saying that you should live your life beholden to someone else just because they're supporting you financially? Isn't that servitude?
Beholden to someone? Servitude?

I'm simply saying that it's unethical to live off of someone else's salary, in marriage, while trying to find a replacement (it's called an affair).

Ten years is a long time, and people change significantly. Think drug abuse. If your SO is strung out all the time, and you have no ability to support yourself, what would you do?

Unfortunately this isn't a corner case. It's a sad but common story.

I'm not judging, I get every situation is different. It sounds like you're referring to a specific incident, 10 year+ relationship, things change, spouse is a drug user.

Sounds awful. My opinion is still that one should leave the relationship ASAP, regardless of how difficult it is financially. Support groups, family, part time work, driving uber, whatever it takes. I think it's unethical to stay in a relationship for financial security while trying to find a replacement.

Even if there was emotional or physical abuse my answer would be the same. Exit the relationship, find support, don't have an affair.

Realistically, where would you suggest finding support to get you out of this situation?

(I'm genuinely hopeful for an answer.)

> . If your SO is strung out all the time, and you have no ability to support yourself, what would you do?

You should work out your issues, remove the things in your life that are causing you harm. (That relationship) Then date later. Moving from one bad relationship to another is a huge redflag.

You're beholden because you're married, not because you're a slave. You have a choice of divorce, nobody is stopping you from leaving, being financially dependent that doesn't justify cheating on your spouse.
Yes it is unethical, but she is unethical more.

Pragmatically, if she dates you while wearing that ring, chances are she will date another dude while wearing your ring.

If you need to stay on toxic relationship because of money, it is hard to leave, but not because you did not dated on the side. It is because you need to arrange living and job (or shelter). People in toxic relationships tend to be emotionally drained.

Seems like a stock photo to me
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It's a stock photo, you're reading into it too much. I doubt the guy went on a date and then asked the gal to strike a pose: "I'm writing an article about how I'm dating 150 girls, can you please pose for a photograph?"
He did online dating, meaning all the girls had already published their photos in the internet before he met them. Just right click and "Save as" would do the trick, if he really wanted to include real photos in the article :)

But yes, I also think that's a stock photo.

Somewhere out there is a girl spamming the hell out of online dating services, looking for this dude. Let's hope when their bots meet, they're programmed to exchange numbers.
That would be the most romantic story IMO.
Truly, the romantic comedy for the late 2010s.

Actually, could be a nice quirky film - and profitable too. Romcoms are cheap to shoot. We're past peak American-romantic-comedy (I think) so the whole "ugh, not another one" factor might be actually pretty low in 2017. So yeah, could be pretty nice.

It's a nice example of looking for the keys under the light aka if all you have is a hammer, everything looks like a nail.

A bit more interesting analogy would be the Big Data craze. We do them because we can. Are the results produced by Big Data as relevant as the dating automation? Do we understand and handle them as effectively as 150 dates with zero involvement? And what do we miss instead? Whose time and place is taken by getting lost in superficial data oceans?

"150 dates without success" --> what happens when engineering meets the red pilled world of dating.
Seems like the problem was that his bot didn't filter very well and ended up matching him with tons of people that he had to instantly reject on the date.

I wonder if there is a mentality problem here too. He had invested so little into each date that there was little incentive to put in the effort to pierce the surface and look for common interests.

Going on 150 dates and not finding a single match tells me that you are shooting outside of your league. Your perfect match could do better than you, and is already taken anyway.

Yeah, either his "optimal" picture made him look a lot better than he looked in person, his personality was off, or he was really picky. 150 dates in a place like the bay area, where probably lots of his dates had something in common with him (blogging, tech, etc.) and not being satisfied with any that liked him back? That seems crazy to me.
He starts off describing himself as short, bald, and fat. I'm guessing that picture is old or he has a distorted view of body image.
Exactly, should've used ML.
> Going on 150 dates and not finding a single match tells me that you are shooting outside of your league.

Total nonsense attitude. You should never feel "outside of your league" for many reasons, particularly since you never know who you are compatible with. Don't be afraid to aim high in a partner.

The flipside is "be brave enough to be alone forever".

If you set impossibly high standards you are just wasting everybody's time.

Sometimes we get so wrapped up in could, that we don't spend the time to ask if we should.
151st date is the charm.

This is a bit like living in NYC for both parties: there is so much volume that you can't get past the first minor disappointment.

I think the volume prevents you from focusing on one person to figure out what you want.

You might want to focus some kind of algo on the second part of the dating: selection.

Don't just go on your gut or how you felt after the date. You need multiple dates to figure that out.

NYC dating: water water everywhere but none that I'll drink more than a sip of in anticipation of finding a better glass. paradox of choice indeed.
I’m a fat, bald, short guy whose only quality is that he isn’t an ax murderer.

Cart before the horse. Also, smiley faces are kinda creepy in your first message.

Step 1, for success, is moving away from the Bay Area.
> Step 1, for success, is moving away from the west coast

FTFY.

I'm not joking either, for straight single men they will certainly have better odds in the midwest or south. Demographics plus minor cultural differences matter.

Not true. LA definitely has a lot of the kind of women that nerdy engineers like: career focused, successful, intelligent etc.
Wow, the data point about rape is an interesting tangent. I guess with people like 45 and all the stories from Silicon Valley, it's not that surprising. But sad none the less.

Maybe we can follow the OP's lead and use technology to automate data collection around this and come up with better solutions.

I think that he needs to improve his conversation skills first.
Opens with the secretary problem and shows no evidence of actually following the algorithm.
I'm guessing because the secretary problem doesn't have this twist:

>Dating is like enterprise sales. When your customer goes for a competing, more compelling product, you’re never told and you don’t get any feedback.

Maybe learn how to treat another human like a human and step out of his own head for a second, might work better than 'engineering' love
Platitudes won't teach somebody how to be more dateable.
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Ehh... the issue is mostly that online dating doesn't go very well for the vast, vast majority of people. On the other hand, I know plenty of not-particularly-attractive people who've met partners through all sorts of weird and whacky situations.

Fact of the matter is that finding potential partners, like finding anyone, is about constantly growing the network of people you interact with. I meet new people nearly every week through various communities I'm part of and organise. Many of them stay that way, just "part of my community", some of them become great friends, and very few become partners. You're unlikely to manage that while working 80 hours a week, going to the bar once or twice a week, and otherwise not being involved in much.

Also, speaking personally... the sort of person who thinks it's fun to spend their time automating personal interaction is not the sort of person I want to date.

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>Also, speaking personally... the sort of person who thinks it's fun to spend their time automating personal interaction is not the sort of person I want to date.

forgive me for waxing poetical but i've thought about this a lot - since i have tinder and okcupid accounts - online dating is one of the most nihilistic enterprises to come out of the digital revolution. take one of the most personally rewarding and edifying experiences and completely formalize one of the most exciting parts of it (if not the most). what becomes the point of your life???

i read a stupid platitude somewhere that you should do something that scares you every day and approaching people you're attracted to (not on the street you pua twats) is one of the few "scary" things still available to us as denizens of modernity (i'm not sailing over the ocean blue, summiting mt everest, hunting moby dick, etc.). why would you want to sidestep that.

>online dating is one of the most nihilistic enterprises

>approaching people you're attracted to (not on the street you pua twats) is one of the few "scary" things still available to us as denizens of modernity

Online dating is good for people who simply have NO other avenue to meet people. If you're not supposed to try to pick up people on the street, then where would you apply this advice? Work? I don't know about you, but I'm a software engineer, so there's no single women at my workplace. School? I graduated quite some time ago, and work now. Church? Like many technologists, I'm irreligious (and I wouldn't want to date a religious woman anyway; been there, done that). Extracurricular activities? Sure, but the number of single women at these things tends to be pretty small, so it's a LOT of effort for very low odds of success. Any many of my interests just don't have very many single women participating anyway.

The simple fact is, online dating offers a way for people to meet who otherwise simply wouldn't. This problem isn't new either; ever hear of "singles mixers"? Those were around long before the WWW came about. Online dating just moves that kind of thing online, and gives you a way of screening people before taking your time to meet them in person so you can make sure you're at least a little compatible. The main problem I personally see with online dating is that there aren't enough people using it (esp. female, they're far more reluctant to use it and see it as a point of shame), and there's too many different competing services. Oh yeah, and all the liars too. But that's nothing new, men picking up women in bars have been lying about themselves forever too.

> Online dating is good for people who simply have NO other avenue to meet people

Like everything, in moderation it works great. I'm a male software engineer and can relate to your feelings of not being able to meet single women naturally. But relying exclusively on online dating is kinda... uncreative. You mentioned bars. But also: coffee shops. Art shows. Music festivals. When used in conjunction, Online dating is great, because now you can invite the women you meet online to join you in the other fun activities going on in your life.

I've never really understood the entire Art Shows/Music Festival angle. I've been to a few and never really been in a situation to actually talk to people.
Of course I can't speak to your individual experience. But these are events where a lot of people are in close proximity and hence the chances of meeting others increase.

In music festivals, the last few women that I met were: sitting next to me watching music, in a line to get beer, dancing to my favorite band etc. It seems to me the social norm in the US for the guy to first initiate contact, so you've gotta be able to do that. Women generally have never initiated conversation, except the most extroverted ones.

I like Art Shows/Museums better because they tend to attract a little more educated/sophisticated crowd. I mean, to be fair, I don't go to these places with the explicit intent of meeting women, but the last time I was in MOMA in Houston and there was a group of ladies talking about Napoleon and I couldn't resist asking questions... it was a great conversation and sharing of minds!

I'd totally be down with a book club where the #1 rule was don't talk at book club. The club therefore consists of people willing to sit in the same place at the same time, and read their own books without ever ruining them by discussing them. Relationship interest would be telegraphed by slightly overlapping your cone of personal space onto someone else's, and hoping it doesn't make them panic and flee.

Nothing spoils a potential relationship quite like finding out the other person is a babbling idiot.

>But also: coffee shops.

I've spent plenty of time in coffee shops. I've had a number of first dates there too. I have never seen anyone introduce themselves to someone in a coffee shop, unless it was obvious that they were planning to meet there. Instead, most people I see there are busy: they're either with a friend(s), or they're busy working on their computer. They're not there to get picked up. If I were a woman, I'd be annoyed if I couldn't go to a coffee shop and relax without a bunch of men hitting on me.

>Music festivals.

If you don't share the same taste in music, that's going to be a problem. The concerts I go to are filled with men. Besides, I've never been to a concert where people were walking around mingling and meeting each other; they were there to listen to the music, not socialize.

> If you don't share the same taste in music, that's going to be a problem. The concerts I go to are filled with men. Besides, I've never been to a concert where people were walking around mingling and meeting each other; they were there to listen to the music, not socialize.

I don't disagree. It can be hard to find activities which are popular with both sexes. I don't really know what to tell you, except that, I'm sorry you didn't luck out in being interested in any of those activities. I would suggest trying to develop a taste for other activities, but I don't think its in my place to ask you to do anything :). I am after all a stranger on the internet.

> I've spent plenty of time in coffee shops. I've had a number of first dates there too. I have never seen anyone introduce themselves to someone in a coffee shop, unless it was obvious that they were planning to meet there. Instead, most people I see there are busy: they're either with a friend(s), or they're busy working on their computer. They're not there to get picked up. If I were a woman, I'd be annoyed if I couldn't go to a coffee shop and relax without a bunch of men hitting on me.

I agree here as well. If you read my other comment, you will see that most of my interactions are incidental, not forced. Its hard to explain, but you have to develop a certain social awareness and curiosity.

Honestly, I've had people pick up conversation with me in a coffee shop on occasion - either they overhear me talking to whoever I'm there with about something they're super interested in, or they're honestly just bored and I happen to be nearby.
"Extracurricular activities? Sure, but the number of single women at these things tends to be pretty small,"

Different extracurricular activities? Like dancing class or climbing - both being social and popular among women.

It's said that it's a very bad idea to do that. Women go to those activities to have fun, not for single guys to hit on them.
That is true. But I think that part of secret is to find activity you genuinely like on itself and then not hit every girl that talks to you. Instead, just socialise, do activity, observe people and ask a girl that looks like long term material based on previous non dating non hitting interactions.

Basically, do selection before you date them - that is what meeting girl "naturally" is. Most girls are not good long term match for most dudes - hitting at random is bound to fail many times (unless you are super accommodating type able to adjust to anybody).

I'm going to echo what the other guy said: going into an activity like that just to pick up chicks is not both insulting to the women there (they didn't go there just to get hit on by single men), and not really that helpful for you: you're essentially lying, by claiming this is an activity you also enjoy, when you really don't and you're just there to meet women. (If you really did enjoy it, you'd already be doing it.)
> take one of the most personally rewarding and edifying experiences and completely formalize one of the most exciting parts of it (if not the most). what becomes the point of your life???

Yea, so the early part of dating may be the most "exciting", but that's not why I date. I find that love goggle time period to be a huge waste of time when 6 months to 1 year later you realize you're completely incompatible on core issues. God help the people who got married during that time period.

Online dating let's you pre-screen for basic compatibility before meeting (and confirming physical interest). It keeps you from making silly mistakes with people who can't make you happy long term.

In my opinion going on a date is also too big of an investment to find out whether or not you 'match' with somebody. When you are at a party you can potentially speak to 10 (20 maybe even 30) women/men in one night, and probably find out that you do not match with 90% of them. If you are using apps like Tinder it will take you 10 nights to date 10 women/men, which is a significantly bigger time investment. Recently I was thinking about this figured out that this is probably the reason none of my friends, who actively use dating apps, have gained any significant relationships using them. This doesn't mean they are not good for anything. However people should be more aware of this and realise that though it seems easier to find meaningful relationships using these apps, it can also make it significantly harder.
I suppose it's a compromise. Using your example, a LOT of people simply don't enjoy going to parties with rooms full of people to try and talk to maybe 30 women/men in one night. Sometimes they find it boring, sometimes they get anxious, sometimes they find it intimidating and wouldn't know how to signal interest without being weird (parties can be confusing that way; most people aren't there to meet a date or hook up). Contrast it with Tinder and similar apps: while people sometimes pretend "a friend installed Tinder on my phone, I never use it!", everyone knows what everyone else is there for, and what they're signalling when they swipe right or start chatting with someone.
Huh, I suppose it depends on what you're looking for. Getting in depth about politics, religion, attitudes towards rearing children, commitment to finding a partner, etc. doesn't tend to be appropriate at parties (since most people are there for a good time, not to find a partner), but they are perfectly appropriate online dating chats.

I don't find it hard to find attractive, fun people who want to date me. I find it hard to find a partner; online dating it takes me usually 2-4 months. IRL it can be years.

Not a bad strategy even if it didn't work, dating is often purely a numbers game.

Meet as many people as possible, be as social as possible, create as many opportunities to meet new people as possible.

Also if you're a single male and you want to meet a female partner, I'd recommend moving away from the west coast. The south and midwest have far more women, and a generally friendlier culture which can make the entire meeting/dating process a bit easier.

The women in the South are generally far more religious and conservative. West-coast men might not be too interested in that stuff.

The "friendlier culture" of the South thing is a myth. They're not that friendly to people who don't fit their preferred mold.

Source: grew up in the South. There's a reason so many young people move out of the South as soon as they can.

> The "friendlier culture" of the South thing is a myth. They're not that friendly to people who don't fit their preferred mold.

Heh... Ain't that the truth.

Completely anecdotally, I got a LOT more Tinder matches when I was in the West/East Coast than in my home state of Texas (I'm a Nonwhite Male).

Having lived in the South long enough to mildly dislike it, I wouldn't say that Southerners are friendly. They are polite, and only when someone whose opinion they may care about is around. Midwesterners are more apt to be friendly, but with far less concern for politeness.

Southern conversation:

  A:  You know, B, we have been friends for a long time.
  A:  I think you ought to know: I'm homosexual.
  B:  Oh, bless your heart.  Thank you for telling me.
  B:  I'm gonna pray for you, A.
  B:  [never speaks to A again]
Midwest conversation:

  A:  You know, B, we have been friends for a long time.
  A:  I think you ought to know: I'm homosexual.
  B:  No duh.  When was the last time you looked at yourself?
  B:  Why do you think the rest of us call you "Mothball"?
  B:  Stays in the closet, and also stinks.
  B:  Guess we'll have to come up with something else now.
  A:  You're a great friend, Farticus.
From my friend group there are two types of individuals:

1. Individuals who date many people, breaking up if they find something non-optimal. These include minor things like, not cleaning up on occasion, or not liking something you do.

2. Someone who dates very few (1-3) individuals, sticking with them until a serious, fatal flaw appears, like being racist or physically harming others, etc.

If you define a successful dater as someone who has both longevity and quality in a single relationship then Group 2 has far more success in their relationships, in my experience.

Group 1 is mostly women and group 2 is mostly men.

At least in my experience.

Unless the majority of people you know are gay, that isn't possible.

For each hetero man you know following strategy 2, by definition, there is a corresponding woman (his partner).

And vice versa with the women who are using strategy 1.

Not true. It's perfectly possible you have a scenario where for example the top 10% of men date 100s of women, the bottom 50% date 3 or fewer women and women have a much more even distribution and date an average much higher than 3. These numbers are just an example but in reality I think something a bit like this situation does actually exist.
Sorry, forgot about this post. It seems you are likely right... (my brain is feeling a bit foggy on this one right now). I can see what sort of asymmetric distribution you are talking about. This must have been studied at some point -- it would be interesting to see some hard numbers.

Anyways, thanks for the correction.

I don't understand. What's the relationship between one person's dating strategy and another person's dating strategy? What's about gays?

Also, I don't see why, for instance, there wouldn't be something like a population where everyone only tries to date as many people as possible. Are you assuming that people wouldn't ever date the same person again?

That doesn't mimic my own experiences. The wajority of women that I have known well enough to observe have been willing to put up with a lot of nonsense. The majority of men that I have had the chance to observe, have had more partners.

Hell, I'm a nice guy and I'm not even sure why the missus puts up with me. (I try to get her to use at least one obscenity a day. Old ladies who swear crack me up.)

I do wonder if this a generational thing? I'm kinda old.

Not really disagreeing with you, but your conclusion is almost necessarily true, which says something about Strategy 1.

One thing on my mind lately is how often people convert from one strategy to another, and how that's patterned and why.

What about people who date few individuals (2-3), break up 1-2 times and their partners were neither closet racists nor violent nor anything that grave. That would describe majority of people I know.
well, the definition of a "fatal flaw" depends on the individual. even falling "out of love" with someone is obviously a fatal flaw which is probably the most common.
Falling out of love is big deal and reason to split, but hardly reflects badly on partners character the way racism and violence does.

If you are neat freak and she is systematically messy, than the relationship is bound to break or be lifelong hell. However, it is no violence and both partners can move to different successful long term relationship (this time being smarter and checking cleanness standards compatibility before first kiss).

"how did you meet that guy?" -Ow, he had a bot on tinder and I responded to it.

Not the most romantic guy, despite his date ideas. Approach a person in public with a tape recorder, so you can just wind it back and go to the next woman.

I find this creepy and weird. How could you possibly tell the love of your life (if and when you found that person) that they were nothing more than a toy in your little data harvesting exercise.
Also -- here is a good moral thermometer:

"PS: I will not open-source the code since it could be used to hurt people, but I might share it if you ask nicely."

If you write code for fun (not commercially owned IP), and you are not willing to share it because 'it could hurt people', you might want to re-evaluate if you should write it in the first place.

Personally I think his approach here was really awful, but for this particular thing you could argue that the code is OK if used by one person, or a very tiny number of people, but if it were used by many people it'd be a big problem. There's a lot of things like that.
I think anyone who has been single long enough to experience the soul-draining tedious world of modern dating could understand and appreciate a way to optimize any part of matchmaking.

Also, I think "speed dating" is just a less geeky version of this.

Glad I'm not the only one... I mean I get the 'hacker' appeal of this, and why it's on HN, but at the same time it's so impersonal and weird to message that many people.

I can't see how almost all of the HUMAN BEINGS on the other end wouldn't find their treatment in this exercise at least a little bit disturbing.

Interesting article, but in the context of serious process and scientific methods, the rape statistics quoted in the article is the exact opposite. The "1 in 5 US women is estimated to be raped before age 25" comes from a single study where they did a voluntary survey in one US university campus. It reflecting of the set of students during that year on that campus that decided to answer that survey. The national average today could be 1 in 5, it could be much more or much less.
Not entirely true, from what I understand. The statistic has been replicated in polls and surveys across various college campuses. The OP's representation, and yours, is a little clunky but makes rational sense to me.

His quote is "1 in 5 US women are estimated to be raped before the age of 25". This statistic is based on surveys conducted by the graduates of various colleges and universities. My understanding of the results are: of all the responding women, roughly 20% claim to have been raped. If the sample of women attending University and/or responding is representative of the population as a whole, then the original claim makes sense.

More to the point, refuting the single study, voluntary survey at one US university campus.

Washington Post-Kaiser Family Foundation Poll. "the poll surveyed a random national sample of 1,053 women and men ages 17 to 26 who were undergraduates at a four-year college — living on campus or nearby — or had been at some point since 2011. They attended more than 500 colleges and universities, public and private, large and small, elite and obscure, located in every state and the District of Columbia." [...] "5 percent of men and 20 percent of women said they had been sexually assaulted in college" http://www.washingtonpost.com/sf/local/2015/06/12/1-in-5-wom...

Campus Climate Survey Validation Study " Surveys were completed by more than 23,000 undergraduate students (approximately 15,000 females and 8,000 males). The average response rate across all nine schools was 54% for females and 40% for males" https://www.bjs.gov/content/pub/pdf/ccsvsftr.pdf

Sexual assault != rape.

Case in point, I've had a random person grab my junk at a gay bar. Technically that's sexual assault, but it's a pretty far cry from rape.

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The Campus Climate Survey Validation Study has on page 18 a summery of the result for undergraduate females during 2014-2015 in the 9 schools:

Estimated sexual assault: Averaged 10.3%, and ranged from 4.2% at School 2 to 20.0% at School 1.

Estimated sexual battery: Average 5.6% , and ranged from 1.7% at School 2 to 13.2% at School 1.

Estimated rape: Average 4.1%, and ranged from 2.2% at School 9 to 7.9% at School 5.

Across the nine participating schools, 4.3% of sexual battery incidents and 12.5% of rape incidents were reported by the victim to any official.

So according to it, the average rape on those 9 schools were 4.1%, but only 0.5% were reported. If we accept those numbers (54% response rate, common location and (likely) background, generational age), we have that out of 150 women that this article talk about, 6 women is estimated to have been raped, in contrast to the initial assertion of 30. The "1 in 5" study was a good signal that further studies was needed. The CCSVS can be seen as a good start of such further studies. The range difference of 400% between school 9 and 5 do say that we need to be careful and bigger studies/meta studies is needed to remove outlines and get averages and median value. In the mean time I suggest the nice and round number 5%, or if the assume that the above numbers are exclusive (uncertain if thats true), 20% that a undergraduate will be victim of some form of sexual misconduct.

So, when will pydate be available on github?
From solely reading the headline I had no idea how far the author took this. Kudos for this very interesting piece of "research"!

I am surprised by the horrible outcome, though, since meeting 150 women is quit a lot. I'd have expected to see at least a short-term relationship coming out of this. It's almost like those generic (but in no way bad) messages exclusively attract the "wrong" women.

150 women seems like a lot... but not if you have a persona that turns most women off.

Women are giving him a chance. He is simply not meeting their expectations of being fun / exciting / confident / funny / whatever.

Slight tangent, but how do you script interaction with a mobile app like Tinder?

For the web, you use a headless browser. But what about automating interaction with mobile?

People have reverse engineered the API, there are libraries for it on github.
Bingo. Use wireshark to identify the protocol and if it is http then use mitmproxy.
Pure speculation: you could run an Android VM and used an automated testing framework to drive it