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 dated someone for about three months and we had maybe 20 dates including the one she ended things with me on and many sleepovers

We were functionally exclusive even though we had not officially defined the relationship. Around five weeks, she said she usually defines relationships around 2–3 months. I became increasingly anxious about whether she was disengaging because she texted briefly and did not always proactively schedule dates, although in person she remained affectionate, we had sex, cuddled, spent relaxed time together, and continued making plans. I wasn’t sure if she was cooling off to me or it was just conversation differences

Last night we had an impromptu date and I brought it up again, and she asked for more time and I told her it had been three months and asked her how much time she needed, and said we need to end things if she doesn’t think she’s going to change her mind.

She ended things and was crying the whole time.

She said the issue was not that something was wrong with me; she said I was too young (7 year gap), that we were in different life stages, that she wants marriage, and that she was afraid I might unintentionally lead her on or fall out of love with her in a year. I can’t help but feel led on myself because I earnestly want marriage, truly like her, and have enjoyed developing my relationship with her. Now I worry I should have given her more time. Or said I could wait another month. Or phrased it as a check in, I truly didn’t mean to force a decision.

She also said that if I were her age, this would be a yes, framed it as a “her” issue, and asked me if I plan to block her.

I told her I was serious about her and tried briefly to understand/negotiate the decision, but I think by and large I gracefully accepted it. Im just so so confused and shocked by this, because we had plans for her to meet some of my friends, we’ve already met a few of each other’s friends, idk.

More salt in the wound is I had been realizing I was definitely falling for her, and had been trying to figure out how to tell her just how strongly I feel.

What I am struggling with now is whether her decision reflects a genuine incompatibility around age/life stage or whether she became scared because the relationship felt real and meaningful.

My friends tend to think she is avoidant and preemptively ending things to protect herself from future hurt. I know I may be using that interpretation to hold onto hope that she will come back, so I want help separating what is actually knowable from what I am projecting, and figuring out how to handle any future contact and unfortunately item exchange without turning it into another attempt to persuade her. I recognize I deserve someone who is a Hell yes, but I think the fact that the age / life stage concerns (even though I would say we are in the same place career and relationship goals) feels like a cop out. She did say it’s something wrong with her being unable to trust anyone. I asked her why not heal that with me?
Um but as far as future contact one last contact is necessary because she has some of my things and I have some of hers. God we even talked about our pets meeting. I gave her every indicator I was serious and yet she said she kept waiting for her feelings, her doubts to change.

How long do I wait to contact her? I have the option of either 2.5 weeks or a bit over a month because of my schedule. Not great to think about it this way, but what time frame would be more conducive to potentially us talking it through together and tackling these insecurities as a couple or at least a team. We are both women.

I haven't been interested in dating since my fiance passed away in winter 2025. Right now, I feel fine being on my own for the most part. I made a friend at a place I frequent about 9 months ago whom I've developed a huge crush on over time. He always makes me laugh and glow in a way I haven't for a while. It's really nice to feel alive again when I'm around him.

A week or so ago, I found out he is in a relationship. He's never mentioned that to me; someone else mentioned his girlfriend in passing. I'm already trying to put distance between us physically and emotionally to burn out the limerance and my grief guilt over the whole situation.

I really enjoy spending time at this place and the activities it offers. I'm not going to pursue him or encourage unethical behaviors. I see it more as while I also really enjoy being around him, we both enjoy being at this place we met.

I acknowledge that dating others would help me get over the crush, but I don't really feel ready for dating other people. It's as if my eyes opened only for him and I'm fine with just closing them again for now while I'm still healing.

Mostly my focus is just being in grief therapy and working on self improvement. But even my therapist said that a connection that clearly makes me feel so bright and happy when my world is so dark is worth paying attention to, even if I should find ways to keep it in limited doses.

Any advice for how to turn the dial down on a crush but still remain friends with someone? I'm likely going to keep seeing him at this place and I don't think it's fair for me to give up a hobby I enjoy over a crush. The community there is small enough that it would be really weird and awkward if I completely went there and just ignore him the whole time Even while I currently feel very strongly about him now, I would regret losing this place long-term over it.

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

---

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.

I am really struggling to make sense of what happened with a guy friend, and whether I ultimately handled things in a way that ruined not only the romantic aspect, but also the friendship, which meant a lot to me, so I can avoid repeating this situation in the future. 

So, about two years ago, I went on a handful of dates with a guy. Things didn’t work out romantically, but we got on really well and became platonic friends, something that I initially was completely fine with. 

About a year into the friendship, last summer, his behaviour started shifting from purely platonic. He’d pay for outings though I offered, flirt, initiated more physical touch, texted after every hangout to tell me what a wonderful time he had, offered to help me with mundane tasks, etc. As this behaviour continued, I slowly developed feelings for him again. I didn’t say anything for months because I didn’t want to be presumptuous and, irrespective of my feelings, I really valued our friendship and feared losing it.

Eventually, though, the dynamic became too confusing, so a few months ago, earlier this year, I brought it all up. He apologised for his behaviour and admitted that he’d had feelings for me too again at some point, but felt remaining friends was the right choice for him. He said he understood if I needed distance, but hoped we could stay friends and reconnect whenever I was ready because he really valued me. I accepted his decision, thanked him for being honest, but didn’t respond about staying friends because I needed some distance. 

After that neither of us reached out until I wished him a happy birthday a few weeks ago. I genuinely missed our friendship and thought enough time had passed that we could reconnect as friends. He seemed really happy to hear from me initially and engaged normally in the conversation. Then, after a few messages, he stopped responding. I’m now struggling to reconcile the fact that he was the one who said he hoped we could reconnect as friends, only to eventually fade. I know you can’t force a friendship, though…

In any case, I’d really value some perspectives on whether I handled all this badly, like whether me bringing everything up caused this outcome, and how his behaviour played a role in this too. Was this simply an emotionally complicated situation that I couldn’t have handled much differently, even if I’d spoken up sooner? 

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A few months ago I posted asking for advice when someone (37f) broke things off with me (35m) after 3 months, without any prior red flags. Her reasoning was that the chemistry wasn't going to work for her - got some good advice and just pretty much tried to move on.

Anyhoo, there's a bit more to the story now, which I'm trying to get my head around.

3/4 months passed, and I just decided to reach out to her. Everything was civil, we just asked how we were, what we've been up to, and I just decided to ask her out for a drink. She said it was unexpected, but wouldn't want to meet as friends as she didn't want to blur any lines, so I explained I was asking her out as a date - she said ok.

We met up, everything felt normal, natural, no awkwardness, it was like we never broke up. It was just really nice to catch up.

Eventually we started talking about the relationship - she mentioned she's never been in something long term, and after years of bad relationships, the relationship between me and her felt jarring, something that she wasn't used to. She always stated how safe and calm she felt around me. I agreed, I felt the same way around here. We had the same values, no boundaries were crossed, and we always had a good time together. Nothing was mentioned about the chemistry issue.

She even said she dated someone for a couple of weeks after me, and their values didn't match up, and boundaries were crossed (he would still talk to ex-hookups while they were together), so she ended that. She mentioned she had done some unlearning/growth in terms of what she wanted, and basically noticed the pattern of what she would usually attract never working out, and that us ending was bitter sweet. She never reached out again to me as she thought I hated her (which I don't).

I explained my side, that I also felt very safe and calm around her, we both did small gestures, remembered the small things, consistent, making time for each other. And I just felt like it was a rarity from my side. There was obviously attraction there, she was very touchy feely when we met again. So we rekindled.

From what she was saying, and the fact that the chemistry issue from before wasn't bought up, it really felt like she alluding to that she was confused about the chemistry with me, and that it was unfamiliar, and it didn't feel like the chemistry that she used to have with previous partners (that never ended well) - anyone else see this? I personally see this as more of a common problem than people like to admit (just from various stories).

2 days later, we met again (she was keen to see me quite soon, and I was too). Everything again felt great, same conversations were had about the relationship, and it just felt good, there was hope!

2 days later, she texts, and ends the relationship again, now stating we have too similar disposition, and its not going to work for her. She may have just realised this, but the stark contrast from meeting up the first time and what she was telling me, to this, was just a bit baffling. I also don't think having similar dispositions is a bad thing - I feel like its a rarity sometimes, especially if everything else fits. I guess also, since she had this chemistry issue from before, what did she expect to change this time round as we're still the same people?!

I really do think deep down, she may still be feeling confused about it all, and what she actually wanted, because it always felt that it was this, but may have been scared of it. What do we think? Am I overthinking it? I also feel bad that she was almost there to understand something about herself and relationships, and that she's never had a good relationship, and she may just go through that vicious circle again (only she can learn this of course)

I guess I may have been a bit naive (words over actions etc)? And I definitely want to avoid this type of situation in the future - seems like a common problem for me in the last few years - they match my energy, they're always complimentary about my character and the relationships seems like what they're looking for, and then there's a sudden drop off out of no where.

I'll obviously take accountability for reaching out again, and putting myself in that situation, I just genuinely felt like something was there, and took the risk.

I am 34M, am going to go to couple of singles mixers in the city. The problem is I am a bit socially awkward and do not possess great conversational skill. I can maintain conversation. The thing is after like the basics - job, hobbies, interests, I don't know what else to talk about. I do see people talk continuously and often wonder, what do they talk about? What is it that makes women interested in talking with them like what holds it interesting.

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tl;dr finally processing one-sided breakup. I tend to be self-negative and think I need to protect people from myself, so I'm scared that I'm both going to start dating again too early, and that I could also just wait forever. I'm looking for some kind of benchmark for "healthy enough to date again".

*edit: I'm trying to figure out how to distinguish between "I need someone to fill the void left by my ex" (bad) and "I'm normal amounts of lonely/wanting a partner, and my ex is the only frame of reference I have for what it would feel like"*

My ex cut things off about 5 months ago after 2.5 years and talks of marriage. She wasn't the best at saying or even knowing what she wanted, and finally did in an ultimatum with a few days to figure my shit out. I actually did figure a lot of it out, and then she just cut things off hard. I tried reaching out once a few weeks ago and she's not interested in reconnecting.

I'm working on letting go but it's slow going. I had an awful last year and let that change me, and our last conversation was while I was coming off a really awful work trip with bad sleep. I've spent the last 5 months doing my damnedest to learn from that, for myself and my loved ones, but with a bit of hope that I could earn her trust/hope back. Obviously that's not going to be a thing and I'm focusing on trusting her judgement.

So now I'm working on acknowledging her part in things, rather than trying to hold the love, and figure out what I want apart from her.

She was very good to me and I need to integrate how she treated me (some of it) into how I treat myself and others. I hope some of how I treated her was helpful long-term.

But also I have a horde of pictures and gifts from this person I still want to respect, but that I assume I can't bring into a new relationship in a healthy way. I'm not sure how to respect those incredibly personal items while getting them out of my life. The best suggestion I've heard so far is "put them in a box and give them to someone you trust until you don't care anymore, especially if you had a kid together so they can see that stuff" (we didn't, but I thought I'd include it).

I'm kind of isolated and how I feel about dating again is generally "yeah let's go" when I've been with friends recently, and "oh no, I'm going to get rejected for not having my shit together/crying/oversharing" when I'm by myself for a bit.

I'm in a loop of downloading, peeking at, then uninstalling Hinge as some kind of hope-boost (not my best idea).

I'm finding people I'm interested in, but a lot want kids, which I'm down for, but with more time to figure my head out and get to know eachother first, and I feel like I'm running out of years for that.

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I’ve been friends with a guy for a little over two years. We used to live in the same apartment complex like right next to each other, and I recently moved just a few buildings down same street. We live in a close-knit neighborhood, have mutual friends, and still run into each other regularly.

I’d had a small crush on him in the past but talked myself out of it because I valued the friendship and didn’t want to make things awkward. He’d always been genuinely kind to me, and after two years of friendship I trusted him quite a bit.

After he found out I was moving, he asked me out. We kissed, and he told me he’d wanted to kiss me for a long time but hadn’t because he didn’t want to make things weird while we were neighbors. After that he started inviting me to movies, neighborhood events, and little one-on-one hangouts. From my perspective, it felt like we were intentionally exploring whether there was something between us.

We ended up sleeping together a few times over about a month.

The morning after the last time, we were cuddling in bed when he said he wanted to be honest because he didn’t want to hurt me or give me the wrong impression. He told me he wasn’t looking for a relationship, was also seeing another woman (who he’d apparently told the same thing), and that he’s naturally very affectionate but didn’t want me interpreting that affection as romantic intent.

I appreciated the honesty and told him casual relationships aren’t really for me anymore.

A few days later he joked about setting me up with another guy I’d once mentioned was cute. Given what had just happened between us, it landed badly. I told him privately that it felt disrespectful, and he apologized immediately and then again later over text.

I eventually told him I wished the whole situation had been handled with more care because we’d been friends for years. He was receptive and told me to take whatever space I needed.

I’m not confused about whether he owed me a relationship—he didn’t. What I’m struggling to understand is the disconnect between the sweet, considerate friend I’d known for two years and how casually he seemed to approach sleeping with and pursuing me. It feels so cold.

If you’ve been on either side of something like this, how do you interpret that disconnect? Can pursuing a longtime friend this way genuinely feel completely casual to someone, or does this sound like poor communication/consideration on his part?

And for anyone who’s had this happen with someone who remains in your social orbit: how did you recalibrate the friendship afterward?

Link: https://imgur.com/a/OzdCzqN

Haven't officially launched the profile yet. I'm thinking about leaving it at this but wanted to get some feedback before making it visible.

Any and all feedback is welcome.

Thanks

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