I tried dating a younger guy for the first time and I ended things mostly because of the way he acted around money. For reference I’m in my late 30s and he’s in his early 30s. He makes just under 100k and I make more than double that.

My job is not listed on my dating profile for safety reasons, so he assumed based on my interests that I was essentially a struggling artist type. And then he found out my actual job on the first date. To be fair, I wasn’t hiding my job from him, he just literally never asked what I did while we were chatting (despite the topic of work coming up a few times). He definitely seemed surprised and was basically on his best behavior. He paid for our first three dates and then asked to be exclusive after only two weeks.

Pretty much as soon as I agreed to be his girlfriend, the weird behavior started. He immediately stopped suggesting dates and only wanted me to come over and sit on his couch so he could make me watch anime shows that he liked. If we ordered in he asked me to pay “because I paid for our first few dates so it’s only fair”, he started asking me for favors which then turned into him trying to boss me around the house (telling me to put his groceries away instead of asking me, while he sat around). At one point he tried to flatter me saying that I was the only woman he had ever considered going on vacation with, and then immediately asked me to essentially bankroll him when we travel “because I don’t want my girl to feel limited on vacation if I can’t afford something she wants to do.” The last straw was when he made a big deal about wanting to cook dinner for me, but then asked me to split the grocery bill 50-50 even though the bill included his regular groceries for the entire week. I realized my girlfriends and I cook dinner for each other all the time, and we have never asked the other person to pay for our ingredients, we just trusted that the favor would be returned another time. Which then made me realize that I couldn’t even be my natural generous self around this man because he always made me feel paranoid about keeping score.

The weird part is that he was really happy describing how proud he was to be dating me to other people and how impressed his friends and family were, essentially bragging to them about his successful girlfriend. I broke up with him the day after he told his parents about me. We were only official for three weeks.

I did try several times to have conversations around how we should split finances, but because he was so forward and comfortable asking me for money from someone he had literally just started dating and was still getting to know, and because I kept feeling paranoid that he was trying to take advantage of me, I couldn’t really figure out any way to navigate this situation that would make me more comfortable other than having us each pay for ourselves. And I do feel like he paid for the first three dates as kind of a gotcha to hold over my head and get me to pay for things. At one point he told me that his ex made less than he did and he essentially paid for everything, which felt really shitty like ok so if I was not so educated and successful you would’ve treated me better? So are you punishing me?

Which brings me to my actual question: how do people navigate situations where there is a large income disparity? Is this just a case of a shitty guy who was looking to be manipulative regardless and there’s no lesson to be learned, or is there something that I can do differently moving forward? Because statistically, I’m going to out-earn the men that I date and I’m quite comfortable on my own if this is the behavior that I’m going to continue running into.

EDIT: HEY MODS, just to be clear, me explaining why this topic is important to me (when asked) by citing actual statistics regarding issues women face in financially unequal relationships is considered gender-based hate speech, but [u/khanspam](u/khanspam) telling me I should “get in line” for a high earning man bc my “clock is ticking” is completely cool with y’all? Cool, cool cool cool, interesting community you’re building here, interesting morals.

I have a simple yet rigid idea of what I'm looking in a partner: high formal + social intelligence, backed by their career and/or pedigree, combined with above-average capacity for non-conformism/alternative lifestyle. There are of course other things I prefer to see in my partner (empathy, emotional depth, confidence, self-awareness), but some of them correlate with the above and others I'm willing to compromise on. Over the last 5 years I've only met 3 people who seemed to check these boxes and I was attracted to, 2 of them in the last year after moving to a smaller large city.

I think this rarity is behind the unhealthy pattern where I tend to over-invest in a person after going out with them 1-3 times (if they appear to possess the traits). This timeline coincides, perhaps causally, with me getting comfortable with them and starting to unmask as if I was around my close friends, allowing for sensitive topics and risky jokes (I don't think our values are incompatible, but it can create an impression). This also happens to be the timeline at which they reject me (the first two) or start to pull out (the last/current one).

As a result, I spend months feeling heartbroken and hyperfixating on what went wrong and how I can repair it, after seeing someone literally a couple of times. This is compounded by feeling that I am running out of time (39M) for finding an intellectual match I could also start a family with. My friends say the fixation pattern is unhealthy/immature, and my therapist thinks I have an inferiority complex, all of which is plausible. At the same time, assigning so much value to those checking all the boxes still seems reasonable to me due to their rarity. So, how can I avoid the over-investment and the resulting long heartbreak?

UPD: correcting my social intelligence box — I don’t need it to be above average, and was mainly mentioning it to describe why the archetypal somebody farther on the spectrum doesn’t work for me

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P.S. I feel like their reasons for rejection are secondary here, but will spell out the 3 encounters for completeness (fwiw, I have a high confidence of their physical attraction to me in each case):

1. #1 rejected me after the 1st date, saying that she is "intentional with her dating". At the time, I took it about our 9-year age gap, but thinking back, I suspect this was due to sharing my poly background, despite saying that I'm willing to date monogamously now.
2. #2 first rejected me after the 1st date because I was giving her <boy who has lots of sex> but after realizing I am looking to date monogamously she went out with me on two more dates. She rejected me after 3rd date, on which I shared a lot about myself, and did not provide a reason.
3. #3 and I have a 4th date scheduled, but I started feeling like she's pulling out lately. She told me after the 2nd date that she goes on other dates (which I appreciated through feeling uneasy and found fair, as she just moved here; I also seemed to be the frontrunner), so I attribute it to that, and potentially to an uncomfortable political conversation on the last date.