Let his answer, or lack thereof, be your guide. You don't sound like you're really that interested in him. You have a huge laundry list of potential dealbreakers that would not be a big deal for others your age difference is not large, lots of people date across class lines, etc. His being unemployed is a huge red flag for you, which is perfectly fair. Personally, I would not be terribly worried about any of this unless he started to expect you to support him.
That would be the dealbreaker point, for me. People say "I don't want to work for anyone else! Usually that lasts a few months and then they come back to earth and find a new job. I've been unemployed and not sure what my next move was and living off of savings and Unemployment. It doesn't make you a bad person.
Dating Advice for Dealing with a Jobless Boyfriend
What would happen if you lost your job? Would you expect your partner to stick by you and let you work through things, or leave because obviously you are a directionless leech? Either way, you clearly want to break up. I give you my permission to break up. Woo, I honestly can't imagine what my reaction would have been at 24 if I had been dating someone who put a huge amount of worth into how much money they made and were pretty heavily judging my lack of interest in doing the same.
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I don't think it would have gone well. If it happened today I would just walk away. Having a large paycheck is never going to be a priority for me. Having someone silently steaming in the background about that fact would be like dating tinnitus. It would be a different matter if he was trying to live off your wealth, but he's not. I'm not sure I understand your concern over that, are you worried if he tried to that you wouldn't be able to say no? Have people done that to you in the past? I know circles where big money is what matters, and it sounds like your group is of that mind set.
It's really up to you to judge if you are able to swim against popular opinion, whether the people in your life would accept it or be constantly throwing barbs at the two of you, and how you would handle it if they did. I think this is a good point. I've heard it said before that, when dating someone, you should only plan ahead as far as you've already been together.
So if you're going on your second date, it's a bad idea to buy concert tickets for next month. If you've been together a month, it's a bad idea to make travel plans for next summer.
If you've been together a year, it's a bad idea to buy a house together. You've been together for six months. It's perfectly OK to look ahead at the next six months. It's a little hasty to start worrying about what if this guy never gets his shit together and your kids can't go to private school and you never get to buy that Maserati you've always wanted. So if you see this guy getting his house in order over the next six months, and you really want to give things a try, sure.
If you anticipate him trying to move into your place next month, yeah, seriously, do what you have to do. That is ok though. I have been in your shoes to a lesser scale not six figure income but not minimum wage either. You haven't been together that long, it's ok to end it. Can you see yourself introducing this man to your coworkers, mentors, boss, etc.? Can you see yourself being ok with explaining how many hours you worked last week when you see he is doing the bare minimum or is still unemployed, and then when you want to go somewhere nice to relax Once again, Eyebrows McGee hits the nut on the head.
Reverse the genders, no family and friends would be raising eyebrows. But oh my, the dire warnings that your situation can draw. I say this from my own experience: K, better educated, much more ambitious and driven he doesn't even make lists! But I was older than you, and had a failed marriage behind me, and knew what a treasure I had. Not always in my head, but my heart always knew.
For me, it was that this man has never, once, said an unkind thing to me. Lots of stuff I wish he would say, but coming from my background, honest and accepting has been healing beyond words. It's 34 years and counting My only advice would be to try to stop thinking about the future, and ask your heart how you're doing right now. He sounds like a keeper, but only you know.
How much money were you making at 24? I think you should let him know that his hesitance to get a job might be a dealbreaker for you. His response might be telling. It's not about the money. It's about being responsible. Make your decision based on that.
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Alia of the Bunnies at 4: I'm sorry, refusing to get a job because you don't want to work for other people isn't some brave stance against traditional gender roles, it's just being lazy. OP, you know what he is now. If he never changed, would you be comfortable with him? Would you feel comfortable having this guy raise your kids? Being a role model for them, being responsible for them? Do you want to have kids?
The guy is very young - 24 is very young - and the dream life is not to have to work for anyone else. It sound like he's got enough savings that he doesn't have to waste his time like this, so good for him.
The problem is, you talk about him just playing video games rather than making efforts towards the better life. I don't know the extent to which this is actually the case or whether it just looks that way from your perspective as an older, more responsible person.
Dating Advice for Dealing with a Jobless Boyfriend | Cupid's Pulse
In any case, I think playing video games is a more productive use of youth than, for example, working retail. However, you clearly have different attitudes and this is probably not going to work out. Your leaving him is likely to force him to focus and do whatever it is that he want to do for real, rather than making it easy to drift. If he is ultimately obliged, as sadly most people are, to make the compromise of employment then at least it will be blatantly his own fault. As things stand, it'll feel to him like something you brought on, and then you're done for regardless.
I don't want to single you out or anything, cincinnatus, but while I agree with you that being self-employed or owning your own business is a fine goal to have, and I respect entrepreneurship, I strongly disagree that the best way to go about it is to shun entry-level work. People who own hotels but don't understand what it's like to be a bellhop are not as good at management. Put in your grunt time, IMO. Be at the bottom so you know what it's like and can have a mutually respectful relationship with future employees. Break out your own competitive business after first working for someone else at it.
I once said that in my family, we are all congenitally incapable of working for someone else. Lots of us in the family have small businesses, are independent workers, or have some other position as an independent professional. I am planning to start a company as soon as I get a prototype working and enough capital together. So what do I do now? I work for someone else.
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We all have our own dream of what we would like to do and what would be the best fit for our personalities and desires, but we also have to eat and pay rent. I also get the impression that you prioritize intellectualism and professionalism. But you should ask yourself if you see yourself partnered with someone who doesn't share your same intellectual and professional values with you. If, instead of him being an unemployed high school dropout he was, say, a nursery school teacher of a low level employee at a non-profit, I think the tone of these answers would be quite different.
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