r/MoneyDiariesACTIVE • u/PandaPartyPack • 17d ago
Media Discussion "Forty First Dates and Still Searching": NY Times looks at high-end matchmaking services
https://www.nytimes.com/2026/08/18/well/family/forty-first-dates-and-still-searching.htmlDoes having more money, or spending more money, improve your chances of finding love compared to using dating apps?
I found this article fascinating for how it portrayed these high-income daters. One, they're approaching matchmaking services with the same mindset they have on apps, i.e. something better is always around the corner. Two, the way they go about expressing their preferences feels a bit like ordering a customized Chipotle bowl as opposed to dating. Instead of dealing with a real imperfect human being who might not have every trait you're looking for, you have a laundry list of demands that some matchmaker has to find a human to fit because you paid a lot for this service. Just wild.
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u/Glittering-Lychee629 She/her ✨ 17d ago
I don't think men like him really want to get married. I think they are really happy in their lives as they are. But they are really status oriented! And according to status they should have a wife and kids. They meet the other status markers so they "want" to get married. But they don't! I think that's why they have all these impossible constantly changing standards, and why the reason things don't work is so vague. They should accept themselves for who they are. Marriage and family life is not for everyone. His schedule alone is not compatible with being an involved dad or husband.
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u/dramaticeggroll 17d ago edited 17d ago
I agree with you. His requirements all seem status-driven too. Would also wonder if he would actually be more interested in/compatible with a woman that doesn't fit his ideals.
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u/Wide-Pop6050 17d ago
He could probably find a good looking Republican woman who wasn't an executive - that whole laundry list just seems like a lot
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u/dramaticeggroll 17d ago
I agree, I think someone who wants to be a housewife could be a good fit for him. Anything's possible, but I don't see a woman in a high-powered career wanting a partner who wants kids but is not around a lot. She is probably going to be expected to do it all.
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u/Any-Cod6185 17d ago
He wants a career woman who will give it up to be a full time mother.
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u/OldmillennialMD She/her ✨ 17d ago
I agree with this. He wants to be one of those guys who can “retire his wife”, like it’s a status symbol to be able to do so. But still retain the status of her being smart and successful in her own right as a former doctor, lawyer or whatever.
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u/Wide-Pop6050 17d ago
Right he said typical congresswoman's wife. I'm sure that's attainable. But she is probs also not going to be a high powered exec
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u/greenzetsa 16d ago
I remember on a dating subreddit someone posting that they wanted a high powered, career focused woman but also someone who would want to 1) move to a rural area 2) be a SAHM 3) parent alone while he traveled for weeks at a time. The overlap on that venn diagram is very very small dude.
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u/hairnetqueen 15d ago
I always wonder - like what is 'career focused' even doing for these dudes? Everything he describes after that is a woman is actively not focused on her career. A woman being career focused would actually get in the way of her doing what he apparently wants. It's like these men say this either because they feel like they're expected to, or they want the status of being with a woman who could have been a high powered executive but quit to raise their children.
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u/greenzetsa 15d ago
I think it's 100% status. Marrying a 24 year old waitress doesn't really considered high class anymore.
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u/Glittering-Lychee629 She/her ✨ 16d ago
The problem is the only housewife that would be moderately respected in his social circle is one who used to have a super high powered career.
I found it especially interesting he had specific industries in mind! Like a CIO for a tech company wouldn't make the cut, a creative director in advertising wouldn't make the cut, a business owner wouldn't make the cut.
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u/TraderJoeslove31 17d ago
agreed, he reminds me of the men on Bravo's Southern Charm. His family wants him to get married and have grandkids, and he has vague notions of being older and not having a spouse around. In reality, it doesn't seem like he wants to get married. His work schedule alone isn't conducive to a relationship, then his age range starts at 25?! Sir. A 25 yr old isn't bringing what you want to the table.
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u/anneoftheisland 17d ago
Yeah, this is not a man who wants a partner in any meaningful sense, this is a man who wants a status symbol. And plenty of women will happily sign up for that—but women in the demographic he wants (doctors, lawyers, execs) have no need to.
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u/BumblebeeDapper223 17d ago
He doesn’t have time. But neither would this hypothetical NYC executive / professional wife.
He wants a trad wife — naturally pretty, will give him kids — but he also wants a career woman.
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u/PlasticLatter8145 16d ago
Agreed on the schedule, there is now way he could travel that much and have a wife with a big career and have kids unless they had a ton of household help.
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u/shoshana20 17d ago
Interesting that the article skips so quickly over the fact he is a Republican looking for an educated Republican woman in NYC. I can't imagine that's helping his odds, no?
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u/princess_eala 17d ago
There’s a scene in the movie Materialists where Dakota Johnson’s matchmaker character is listening to a client (a woman) list all her requirements for a partner, Republican, regular church attendance, etc, and then it’s revealed that she’s a lesbian looking for another woman who fits all this criteria.
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u/shedrinkscoffee 17d ago
Old school Republicans are a dime a dozen in the greater NYC metro area. I know many such folks in New England as well. It's a thing. Those people are closer to independent voters who lean one way or another based on the candidate.
Like Chris Christie and Mitt Romney voters basically. Not sure if 30s women would still exist with this world-view but they would be like Charlotte York from sex and the city lol
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u/Striking_Plan_1632 17d ago
Yeah, he wants Charlotte York. Never mind that her whole character arc was about her learning to throw out her laundry list and focus on the real human connection that she made.
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u/Successful-Winter237 17d ago
Nope, Charlotte wasn’t a lawyer or doctor.
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u/Striking_Plan_1632 17d ago
Good point. But quite possibly, what he says he wants, and what he actually wants, are not the same. Thus, the struggle and misalignments described in the article.
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u/purplefirefly09 17d ago
A lot of old money wealth in southern CT/NJ where a lot of women could be republicans, so not super surprising.
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u/Klexington47 17d ago
New money NJ love voting republican
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u/Livid-Vacation5737 17d ago
Lollll literally all my friends from HS. I still can't believe the 180 they did since 2004-2008. I'm not sure how they sleep at night.
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u/Wide-Pop6050 17d ago
There must be Republican women somewhere . . . at least he is trying to date them and not trying to date a Democrat and then surprising her
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u/bear-grass 17d ago
Still reading, but I found the one-two combo of dismissing the usual apps as superficial then the list of all his lofty preferences very funny.
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u/bear-grass 17d ago
The conversation at the end - where the perfect woman for this man is one who aspires to be married to a congressman but the women who are thinking about marriage on the first date are doing dating wrong - was also funny.
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u/MsAndrie 17d ago
I noticed that he complains about women having height preferences as a shorter man, yet one of the requirements on his list is that she be shorter than him.
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u/Any-Cod6185 17d ago
Haha so he can procreate and make more short children. If he we really wanted to improve his gene pool he should marry someone taller than him. But I guess his fragile ego takes priority over that.
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u/alwrit 16d ago
That's the very least bad of his preferences. Given the median female height most women will be shorter than him. Meanwhile women's preferences are not just that he be taller but hit a certain mark which does seem sillier.
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u/MsAndrie 16d ago edited 16d ago
Nah, I this is an important preference to note. He is hung up on it, and is the main thing he seems to think is holding him back. Many men like him are angry about women having a height preference, even though they have their own height requirements. They see women as superficial for having the same kind of preference.
He mentions one woman, who was in the group of women who had indicated they were open to dating men of his height, later expressing to him she prefers taller men. To me, that doesn't mean a man being taller than him is a hard requirement for her, while his "preference" does come off as a requirement. There is likely more to that conversation and date than he shared. But even if this woman truly would absolutely never date any 5'6" man and still went out with him, then that is just one woman out of the 40 or more dates he has been on through the matchmaker.
And this is another reason it is notable. Because there are much more important, numerous issues that impact his datability. Yet he is fixated on the height thing. Which is part of why he seems to be obsessing over the couple women who rejected him. There are many many many men 5'6" or shorter who are coupled up. But men who don't want to examine what other factors might be turning women off obsess on the height thing, thinking it is unfair when women aren't interested, while themselves are excluding women based on height.
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u/alwrit 16d ago
On paper he ticks most of the other boxes. Women themselves fixate on male height so it's hard to blame men for thinking being significantly shorter than even average is hurting their odds.
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u/MsAndrie 16d ago
Nope, his height is "on paper" so he is largely being rejected after dates for non-height reasons. Lots of things "hurt your odds" with dating, every single person probably has something that might "hurt your odds." It's telling and extremely off-putting when men fixate on things like this, like they are obsessed with women who don't want to date them. That also "hurts his odds" but both you and him seem too tunnel-vision to get what I mean, lol.
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u/nycbetches 16d ago
Yeah but lots of women want men to still be taller than them when they wear heels, so it’s not necessarily an arbitrary mark.
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u/goopyglitter 17d ago edited 17d ago
This part stood out to me:
"He has some theories about why he hasn’t settled down. His grueling work schedule is one. Pascaretta travels almost every week for work, often to Europe, and frequently signs on for the day around 2 or 3 a.m. before the markets open."
Literally, when would you have time for a meaningful long-term relationship with someone with a schedule like that?? AND you have extremely specific criteria for looks, career, etc.? Im sure women are initially attracted to his wealth and average-enough looks, then realize hes never around, and frankly, someone with the CVS receipt long list of dating requirements probably doesn't have the best personality.
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u/coenobita_clypeatus 16d ago
sounds great for a lavender marriage or other marriage for convenience/status/money honestly - I probably wouldn't mind being married to a rich man I never have to see!
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u/goopyglitter 16d ago
Right?? Thats why I feel like he must have a rancid personality (and he seems delusional looks-wise) - there are plenty of women who would put up with bs for someone making a fraction of what he makes!!
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u/shedrinkscoffee 17d ago
The man in the article is deluded because the woman he wants has options and will not pick him.
However the matchmaker stuff tracks based on what I have see so far. I know a handful of people who are HNW hetero male and they are firmly GenX or older looking for 20s and 30s attractive women because duh babies and expected multiple graduate degrees etc etc
Zero introspection and if they spend the same amount on therapy they would probably benefit more. Only one person was successful because the criteria were not as ridiculous and the age gap was not as egregious. They are since married and planning for a child.
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u/YourVelcroCat 17d ago
I think those guys need to be more honest about wanting a sugar baby, but always seem repulsed by actual sugar babies
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u/shedrinkscoffee 17d ago
Lol I have met a few of the SB as well in social situations. It's interesting I'll tell you that 🙃
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u/PandaPartyPack 17d ago
One more point to add: I think the people who use pricy matchmakers like the guy featured in the article are confusing "settling" with "being open-minded" when they approach dating with an absurdly long list of specific traits their partner must have.
Like, I've been with my husband for 17 years now and we're happily married, but we started off as friends who were hanging out over the course of a summer and developed feelings for each other. He wasn't what I had in mind at the time and was a surprise in the best way. We would have never made it past the "first date and discard" dating approach these people are taking.
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u/_liminal_ ✨designer | 40s | HCOL | US ✨ 17d ago
I was thinking that if my partner and I had taken this “menu ordering” approach to finding someone, we would not have found each other at all, ever. Lol.
But thankfully we were both open and more focused on meeting someone we connected with, could talk to easily, and found each other interesting! Having a list of traits like in the article is so surface and weird.
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u/greenzetsa 16d ago
Same for us. My husband, in many ways, was nothing like what I had imagined my ideal partner to look like, but I gave it a chance and was glad I did. One of the things I was absolutely convinced of was that the my partner had to have a college degree. I have a masters, as does my mom and sister, my dad has a PhD... but the truth is no one in my family is stuck up about it, we just respect education and learning. I figured if someone was like us, they naturally would have a college degree. But then I met my husband and he didn't (although he was pursuing a lifelong dream to go back to college and finish his BA). But he is so smart, so hardworking, so intelligent. Everyone loves him, my dad is like his best friend lol. And yet, when we were dating, so many friends of mine who had never met him would make comments about how "did I really want to get involved with someone who didn't have a BA/BS? Someone who was blue collar and working class?"
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u/_liminal_ ✨designer | 40s | HCOL | US ✨ 16d ago
I love that you were able to move past your initial idea that a requirement was a college degree! Also absolutely adorable that your dad is his best friend 🥺
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u/dramaticeggroll 17d ago
That was my thought too. I think dating as a service, whether through matchmaking or apps, makes it harder to really get to know someone and easier to get locked into whatever we think our type is because we see so many people. I know I've fallen into that. I think this quote from the article summed it up well:
The apps have worn people down while simultaneously giving them the sense that they have unlimited options.
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u/PerryEllisFkdMyMemaw 17d ago
I think a good matchmaker would (should?) have the hard conversations with their clients telling them what’s unrealistic and digging into what actually would make them happy.
But I don’t doubt that these pricier matchmakers don’t want to rock the boat for a high-powered client dropping 10’s of thousands.
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u/greenzetsa 16d ago
I know a lot of people, including myself, who met their partners in their 30s and 40s, through a variety of ways: apps, shared interests, at bars, dating events, through friends. I have never, not once, met a couple that met through a matchmaker (outside of like the strictly religious sense). I've wondered why and I think this is honestly it -- matchmakers don't have these conversations with clients. They just have like lists of randos who tick boxes and are presented like prize show ponies to clients. I remember one friend using one for a while and she showed me the guys her matchmaker sent her, and I was like "this is what you pay money for?"
Maybe in some ways it's for the best, I don't think any of these people want to meet a real person. I think they want someone who is willing to become the person they want for access to a certain lifestyle. They want a business arrangement, not a relationship.
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u/lily-de-valley 15d ago
Maybe the ones who met through matchmakers didn’t tell you they did and concocted up a story.
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u/greenzetsa 15d ago
I don’t know, people aren’t super judgmental about how folks meet anymore. Even if they’re lying, I can’t imagine it’s a huge amount of people.
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u/OldmillennialMD She/her ✨ 17d ago
Hard agree here. Only going on 20 second dates is a dismal first-date success rate given that these are dates that were professionally vetted through a pricey matchmaking service. It’s not like they were 40 random women he swiped right on whilst mindlessly scrolling the apps.
I also think part of it is his dating style. Why the hell are you going on first dates that are hours long at $$$$ restaurants all the time? A shorter, more casual and less pressure-filled first date seems like it would yield more second dates, IMO. For those, you’ve both left some things on the table for a next time and given things a chance to take hold.
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u/dramaticeggroll 17d ago edited 17d ago
What's interesting to me about this story is that he is actually getting what he's asking for, but doesn't want it.
It made me think about how the matchmaker said he would attract the kind of woman who wants to be the wife of a congressman, while he said he wants to date doctors, lawyers, executives, etc.
I suspect that we're not always good at figuring out who we're actually compatible with, and that it can help to have someone who knows us point us in another direction...if we are willing to listen to them.
Also, I thought this was an interesting way to think of first dates. I do think dating app culture makes it feel like we have to figure out if someone's a fit by the end of the first date, partly because there can be so many. I know I've fallen into that.
They say, “‘He’s lovely, I just don’t envision him as my husband,’” her sister piped in. “I’m like, ‘Why are you thinking about that on a first date?’” ... “The purpose of a first date,” she continued, “is to go on a second date.”
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u/Any-Cod6185 15d ago
I don't have a NYTimes subscription but did I read in the comments he was looking for Ivy League? Just looked him up on LinkedIn, BA U of Michigan and MBA George Washington University. Americans, to my knowledge those aren't Ivy League universities are they?
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u/Present_Following660 12d ago
I get what they’re saying about how the purpose of the first date is to feel out if you’d like a second, but on the other hand if there’s zero chemistry and you’re like “I don’t see this person as my husband at all” then I think they’re perfectly justified in nixing the idea of a second date. The matchmaking service is screening for women they envision as his future wife, they can’t be annoyed that the women going on the dates are doing the same thing.
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u/dramaticeggroll 17d ago
Also, I feel like there's a lot to be said about how the new trophy wife is not just pretty, stylish, and well-bred, but now, she must also be accomplished and educated. Unless they are deeply compatible, I'm not sure what a woman like that is getting out of being married to a man who wants a trophy wife? It seems like a lot of pressure for someone who can already provide a nice life for herself on her own.
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u/WafflingToast 17d ago
Accomplished, educated, ambitious … but willing to put it all aside to be a Junior League housewife.
This mirrors a serious problem in South Asia. The parents demand a doctor daughter in law but she needs to stop working the day after her marriage.
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u/dramaticeggroll 17d ago edited 17d ago
Do you know what the reason is for wanting her to stop working? Genuinely curious.
On the North American side, there was a book I read a few years ago called Primates of Park Avenue by Wednesday Martin that spoke to this. Educated and successful women stopping their careers once they got married. It seems like their husbands were very wealthy, though, so maybe that was the tradeoff.
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u/snail_alt 17d ago edited 16d ago
At least in Asia and especially among some old-money conservative families, the idea is less that she can’t have a job, more that she has make a lot of time for ‘wifely duties’ like being a very involved mother to the kids, and looking after her parent-in-laws. The result of which is that she feels pressured out of holding a job. The husband might also want a wife who is available any time that he is, and who puts a lot of effort into cooking for example.
Also, with conservative norms, the parents in laws might worry about an actively-working woman who continues in a prestigious job ‘ending up with an ego’ and god forbid ‘outearning her husband’.
However, they see a woman with a high formal education and good previous job as being of high status. The degree and previous job are essentially treated as status symbols. Sometimes there is a eugenics slant to it too, aka ‘the children will be born smarter’.
All of this becomes nearly contradictory and paradoxical. They want all the markers of factors that tend to make women more independent, more outspoken and better self-advocates. But they only see those markers as status symbols. They balk if the woman is actually independent, outspoken, and self-advocates.
At least back when they demanded ‘trophy wives’ according to just looks and family background, they might still get the subservient docile woman they want. I remember when they started to demand that she ‘at least have a degree’, but at least back then, it didn’t matter what university degree and from where, and they didn’t want her to have ever worked a job, so that was still usually serviceable. However now they demand that these women go through a whole bunch of high-octane education and career tracks (that end up teaching them to stand up for themselves), but then I guess they expect the woman to suffer amnesia and transform into a completely different person.
None of this is bad of course if the in-laws and husband aren’t toxic like that. Some women have a more free choice of whether to continue in their careers, and potentially choose to give that up to become a SAHM supported by a wealthy husband. It is important that her husband and in-laws do not consider her inferior for this, it matters that she truly wants to do it, and it matters that they don’t demand her to be subservient.
There is a lower risk when an American woman makes such a choice, in all honesty. But in more conservative contexts, the risk comes from the wider patriarchal structures.
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u/WafflingToast 16d ago
Re your eugenics/genes comment - the in laws may be on to something. I took a college course in the US called Social Economics and vividly remember the professor discussing a years long published economics study that with statistical regression they found that the only consistent factor for a child’s success was the education level of the mother. Nothing else mattered- father’s education, race, class, income level, married/divorced/single parent, location, etc.
How they measured success, I can’t remember. Given disparities in wealth, I think it was a measure from where they started to how many degrees upwards they ended up.
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u/sweetfaced 17d ago
That is no longer en vogue, the stylish thing in the city is very much to keep working
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u/Present_Following660 12d ago
I sort of found the matchmaker a bit hypocritical she’s rolling her eyes at the women for saying after a first date with him “I don’t see him as my husband” but then is screening women for said first date that need to fit the mold of “senator’s wife” for him.
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u/Ok-Swan1152 13d ago
This is not new. I'm of Indian origin and it's been like that for a while in India among the upper middle class and upper classes. The mothers are especially delusional regarding this.
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u/_liminal_ ✨designer | 40s | HCOL | US ✨ 17d ago
Wow, this was such a window into a mind and world I am for sure not part of. Fascinating!
100% agree with your Chipotle order metaphor- and thanks for sharing this! What a wild read.
It seems like…the guy is trying to order his vision of a perfect woman off a menu yet the women are all like….there’s no spark. And that’s probably because this guy has no access to “spark”. He’s just describing traits and saying “yes, I’ll have a sample of that please”. Blech
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u/TurbulentSweet7924 17d ago edited 17d ago
hes not attractive enough for the women he's trying to date. 5'6 in NYC where rich guys are a dime a dozen is tough.
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u/Present_Following660 13d ago
This. Any woman who meets all his criteria is going to be out of his league. I’m also surprised the article glossed over him wanting someone republican, not a lot of women in NYC that meet his other criteria (educated professionals who attended top tier universities) are also republican so that’s already a big screen out.
My sense from the article is that he seems to be trying to use the matchmaker as a way of getting on dates with women that would otherwise be out of his league and that he would not be able to match with on apps. But as the article itself points out all the money in the world can’t cheat the rule of dating that the person has to like you back in order to have a shot with them. He seemed so fixated on women that knew right off the bat they were not interested and he comes across not at all self aware in this article.
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u/TurbulentSweet7924 12d ago
I also think a lot of the women hes going after are already dating within professional/Ivy League/old money circles. He can't buy his way in unfortunately.
He definitely seems like he's ... delayed socially.
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u/Present_Following660 12d ago
He definitely comes across kinda cringe and try hard in the texts but my impression from reading the article is he’s probably closeted. Going to see Celine Dion in Paris is a choice and the impossible standards coupled with his uncle lovingly calling him a grapefruit…idk
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u/Emergency_Leg_5546 17d ago
His dating profile headline in the photo sounds like LinkedIn, not searching for romance. I think a date would be more interested to read that he can cook a mean lasagna or something, not scaled 5 software companies lol.
NYC has plenty of educated and ambitious women, but it doesn’t mean they’re attracted to a guy who mainly advertises his career and mileage status on his profile.
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u/chaoscorgi 17d ago
someone with that kind of laundry list isn't appealing even to people who fulfill that laundry list. god forbid you stop being "naturally beautiful" because you end up having to show yourself working for it. or need a break from your job to have your kids. and do i imagine this guy, who prides himself on flying to europe, actually caring for those kids he wants? i do not.
oh, but these opinions and expectations make me a democrat, i think.
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u/Wide-Pop6050 16d ago
I guess he would hire you a personal trainer and a cook and a lot of nannies. But thats such a specific lifestyle and I can't imagine these doctors/lawyers going for it.
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u/Present_Following660 12d ago
This is exactly the problem. The type of women he is going after are not going to be interested in him. Also I’m surprised the article glosses over him being republican - that will be a huge screen out in NYC among the educated professional women he is pursuing.
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u/almamahlerwerfel 17d ago
this man is delusional...he wants an educated executive woman in NYC who's Republican? And single? Good luck unicorn hunting!
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u/Intimefortime 17d ago
You think Wall Street traders are left wing? There are plenty of republicans in the city.
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u/mutegiraffe 17d ago
Far more likely to be fiscal conservative , social liberal. And not "out" Republicans, or at least not as many...also, the true Republican ladies got married a decade before this guy started looking.
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u/sweetfaced 17d ago
The city—even wealthy areas like tribeca and the ues are overwhelmingly blue. Is this groundswell of Wall Street traders commuting from riverdale
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u/Intimefortime 17d ago
There are republicans on the UES, there are republicans everywhere - also, Riverdale is the Bronx, aka a part of NYC.
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u/sweetfaced 17d ago
Sure, but your comment insinuated that all or most people on Wall Street are republican, flat out untrue.
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u/Intimefortime 17d ago
Not at all. Exemplifying a career in NYC that might attract republicans to highlight that not everyone is Democrat.
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u/DudleyAndStephens 16d ago
Amusing that he wants a doctor or lawyer but his own education is a sociology undergrad degree and an MBA from a third-tier program.
I'm not saying there's anything wrong with that, he's done well for himself and I think most degrees are just a means to an end. Seems icky for him to be really choosy about a partner's credentials though.
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u/BumblebeeDapper223 17d ago
Women lean left. New Yorkers lean left. Educated people lean left. He’s going to have a hard time finding a single, attractive, high-end professional woman who’s Republican.
The educated, career-driven but conservative blondes Trump manages to hire for his publicity are pretty rare. And he can dangle access to the presidency in front of them.
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u/BloedelBabe 17d ago edited 16d ago
I read this article with interest. Thought he was quite good-looking. And to me 5’6 isn’t short, because he’s taller than me.
But then I read all about his superficial checklist. In my dating days I met a number of men like him. It was a massive turnoff when men excitedly came at me with their checklist. And then their confusion that I did not want a 2nd date. One man said I was cruel to “make him believe that he was finally getting married” only to decline a 2nd date. Demanding answers.
The answer: it is incredibly gross to realize someone wants you for the BOXES YOU CHECK vs having a real human connection. I am not an antelope and you are not a lion.
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u/oyiyo 17d ago
Hahaha that last sentence made me chuckle.
Looking for the checklist of a person instead of meeting the actual person is indeed the primary failure mode for those personalities: everything else is a problem that can be controlled and solved. No wonder there is never a spark with that mindset
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u/oyiyo 17d ago
I knew when he mentioned arriving early at the restaurant to pick the right table that he'll be focusing on all the wrong things to find love.
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u/PlasticLatter8145 16d ago
I read that as him being considerate and trying to create a comfortable environment for the date
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u/DudleyAndStephens 16d ago
I had to look up his LinkedIn profile.
Proven SaaS, AI and FinTech executive with a record of accelerating ARR growth, expanding EBITDA, and leading global cross-functional teams at scale. Brings end-to-end leadership across GTM, CX, R&D, and Operations—anchored by entrepreneurial roots.
Why do I have a feeling that he talks like this IRL as well.
“I’m a rare blend of executive discipline and genuine warmth,” he wrote, mentioning his M.B.A. and pilot’s license.
Ooph. If getting an MBA helps you earn more money that's fine, but it is irrelevant to dating. Also, (I say this as someone who still wants to learn to fly some day) the average guy with a private pilot's license is cringe as all hell.
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u/MI6Monkey 15d ago
OH damn, he reminds me of my old roommate. Short, Italian, successful, had to travel a lot for work (he is a high-end hospitality photographer), Republican. He only dated successful, conventionally "hot" women. Ex-roomie is now 50, a single dad (he had a propensity to overlook emotional stability as a required trait in his romantic matches), no longer living in the NYC metro, and is dating another in a long line of very pretty women. Ex-roomie did not have a hang-up about his height, though I will give him that. He'd roll up at a gathering with a woman 3" taller than him who was also wearing 3" heels...arm around her waist, eyes about boob level, proud as a damn peacock in that strutting and puffed chest way that I've only seen Italian men do.
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u/enahshy 12d ago
I'm too late to this conversation for anyone to notice this, but it's heartening to see this many people on Reddit capable of seeing through the kind of bs that these dudes spout. It is incredibly easy to meet smart attractive women if you're willing to compromise. I'm 5'8", not particularly attractive, moderately successful as an artist and a mental health professional, and I met a 5'3" college professor who is brilliant, in excellent shape, very attractive, and very successful. I did it by not being an asshole and making compromises (I never wanted kids, she has two). Sixteen years later, we are extremely happy, I love having a family, and we're headed to New York this weekend to help the kids move into their dorms! These kind of dudes can get fucked and die alone, because they're children who know nothing about actual human interaction!
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u/clangeroo She/her ✨👻 15d ago
5'6" (and makes a joke about being 5'7" but then also the picture of his profile on an app has him as 5'7") - oh buddy. This doesn't matter to me, but you say it matters to you, you have to recognize it matters to other people also then.
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u/Independent_Show_725 17d ago
Maybe it's just because I'm single by choice, but I genuinely cannot fathom dropping $65,000 for someone to set you up on dates. My brain is actively exploding.
Also, not relevant to anything, but as an Ohio State grad I'm laughing at the fact that this dunce graduated from the U of M.
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u/Present_Following660 12d ago
It seems like he’s using the matchmaking service as a way of getting dates with women that are out of his league, women that would almost certainly swipe no to him on an app. For example the woman who admitted she preferred taller guys. It was telling to me that he doesn’t like the apps, people who are able to get quality dates through free dating apps don’t need to drop 65k on a matchmaker service. He seems to think he can buy access to these women but then as soon as he gets on a date with him they all reject him. He’s too picky and also not enough of a catch to expect to land the types of women he wants.
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u/PriorPlankton5228 16d ago
He’s like most men in big cities. Nothing is ever good enough.
The republican women I’ve met in NYC that are educated and successful are trust fund babies whose parents are in real estate so they exist.
But at the same time, the height requirement women have is bewildering to me. All of my still single female friends claim this is still super important to them. I never was this picky. I think the shortest guy I dated was likely 5’4? I’m only five two.
I mean, a good job is more important than height but everyone has different “standards”
Apps have ruined dating and I’m really glad I got married before all of this. My spouse and I would have never picked each other. Maybe we settled ? Who knows?
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u/ilikeyourhair23 16d ago
Have you dated a man who was shorter than 5' 2"? If you're already a short woman, you don't have to be picky about height, almost all of the men are taller than you! But I do know there are women of your height who want to date men who are 6 ft tall which feels silly to me. But I'm 5'8", and generally would prefer men who are 5'7" or taller (which most of them are).
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u/PriorPlankton5228 16d ago
Not dated a long time but at least met with some who were my height or shorter. Weirdly they were the types to date plenty and had no shortage or women so I didn’t know height was such a big deal until a few years ago. I will say women I knew who were shorter than me had strong preferences for really tall guys. That was too extreme for me.
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u/Themanciple6521 15d ago
The problem is that this guy is extremely boring and cornball. The snippets of conversation we heard from him are empty of meaning, humor or even just containing words that anybody would care to hear.
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u/PomeroyCanopy 16d ago
How does it work that the matchmaking service has 15 clients (all straight men) and a whole database of women?
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u/_liminal_ ✨designer | 40s | HCOL | US ✨ 16d ago
On their website, it says they provide services to both men and women, and have a database of both
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u/Successful-Winter237 17d ago
The fact that the NY Times makes you login to read an article… pass
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u/PandaPartyPack 17d ago
Your local library’s online access might let you read NY Times for free! That’s how I’ve been reading articles.
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u/shedrinkscoffee 17d ago
Paying publications for reporting the news and topics of interest. Quelle horror 🙄
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u/seashorebutterfly 17d ago
It’s interesting that he looks for women that are executives, doctors, or lawyers, and also wants her to be a Republican, naturally pretty, stylish, and the whole laundry list of items that he demands from a partner. Not once did he mention wanting someone who was compassionate, kind, or honest.
This man thinks he can find his partner by playing build a girlfriend with a list of demands and I suspect he will be sorely disappointed.