TL;DR:

Been dating for 6 months-ish. He (40M) has had a rough go (divorced, felon) and is currently in a rough patch (was employed but has been jobless for 3 months, lives with family–though that’s a mutually beneficial setup). I (32F) grew up on the rough side of town and was determined to get me and my family out, so I kept my nose clean and worked my butt off (never married, no record, well-paying job, own a couple of properties). Being opposites on these didn’t bother me up until recently and has been exacerbated by him not having a job / assuming I will pay.

The Details:

We met online. I think we were both just seeing what’s out there but not expecting anything. Us, being both STEM nerds, end up hitting it off discussing one such topic. Fast forward a month, we’re talking every day, having fun getting to know each other, etc. Then, I find out about his criminal history…on my own…major trust issues introduced. I can understand why he wasn’t forthcoming since we were still getting to know each other, but dang it sent me into a tailspin. But, we survived it; he let me (and still does) ask whatever questions I want about it and I came to terms with it for the most part.

Fast forward some more, his company started making some changes to their policies that he disagreed with, so he quit. When he quit, I think he was expecting to be able to find another job quickly, but that hasn’t really been the case. He has been trying, just having a hard time.

And now to…well… now. The other day we went out to eat and he reached for my wallet and took my card without asking. I don’t mind paying and usually I do, but up until this point he at least waited until I offered. The assumption without asking really bothers me. We’ve talked about marriage, but we’re not married yet, so what mine is still mine. And while I really do make decent money, I’m also bankrolling quite a bit for my family…so money stress is still a thing. I did mention that it bothered me to him and he apologized and said he wouldn’t do it again, but it unfortunately it fed some of the silent worries and has since caused me to spiral.

Big picture: intellectually we match, principles and values we match, importance of family – match, family planning – match, politically – match, the way our brains process info – match, metaphorical guards – match, sexually – match, etc.

Things my brain is having issues with: felony (I keep going back and forth, this comes with some implications that I just don’t know how to feel about), job (grossly, I started feeling embarrassed that he’s unemployed), remnant trust issues (there’s a small fear another bomb is gonna drop), me being expected to pay, and some tiny nitpicky things not worth mentioning.

I just feel kinda stuck. I love him and don’t want to lose him but I also have the logic based argument in my head that I can’t seem to quiet down.

Anyways, any advice is appreciated.

6 comments
  1. Take your time with him. Don’t rush into anything. I worry that you bring up marriage. It’s way too soon, especially since he doesn’t have a job.

    Since I don’t know why he has a conviction, it’s impossible to comment on that. If it’s for something violent, I’d be concerned.

    Assuming you’d pay, even though you generally do, is a red flag. He’s going to continue to take advantage of your generosity until you don’t let him. Perhaps ease up on the dates until he can reciprocate. Keep things very simple for now.

  2. Let’s be honest here. Your 6 months in and he’s already naturally going fir your purse.
    I feel like I’ve read one of those scam marriage stories.

    Op, maybe ask him to back off a bit till he gets himself sorted, his reaction will show you his true intentions

  3. I agree with other commenters, take it slow. It’s okay to “talk” about marriage as a desire right now 6 months in, but getting super serious about it and discussing engagement for real should wait until closer to a year, especially in your current situation. Given his past and him also not having a job or his own place, I think you should give him time to “prove himself” to you.

    Maybe the reaching for your wallet is him being super comfortable with you at this point. It’s a little strange, but I wouldn’t be too alarmed unless he does it again (or something similar).

    How hard is he looking for a new job? If he’s kind of being lazy about it, I would be very concerned.

    Since you did not reveal what he did that makes him a felon, there is not much I can say about that other than trust your gut and decide if it’s something you can live with for the rest of your life as something that is going to follow him around and/or affect your lives together.

  4. Please be careful OP. I unfortunately see these situations too often with my work.(divorce lawyer). Worst thing you could do right now is get married or pregnant.

    Could you imagine being where he is in another 8 years at 40, given how far it sounds like you have come by 32? How can he not have a job when literally everyone is screaming for employees (felony?)

    You may have good chemistry so enjoy that for what it is, but great sex early in a relationship doesn’t mean great marriage. You need to be equal or at least close to it some how and you are doing 100% of the work at this point.

    I recommend slowing down, you can still date him but don’t move him in and pay for everything like a child, he needs to bring something to the table, and from your description I am unsure what that is.

    Tldr: I think your feelings are valid. He is not bringing much to this relationship, and doesn’t sound like that’s changing at all if you are in same spot at 6 months ago. SLOW DOWN.

  5. You just mentioned 4 pretty huge issues.

    It’s been 6 months!! Why the hell are you settling for this?

  6. I think that it would be realistic to try to navigate ONE of these 3 huge issues but not this many. Far too many cons/red flags/ whatever you want to name them. These are all big deals and you’re 6 months in. Stop investing time in him and move on.

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