Views please – Man in late forties financially dependent on parents

If you talk about kids, ask him how he plans to support them.

Thank you K and Tallspicy. So question is – is the fact that a man in his late forties is not self sustaining a red flag? I have never dated entrepreneurs in the ‘start up phase’. So in a way I do not want to rule him out seemingly for reasons to do with his finances. But it goes deeper than this. My prior experience has either been professional guys or self employed, in all cases at least self sustaining. I dated guys who earned less than me who would refuse that I pick up the check out of pride – this is a mindset much closer to my values than feeling OK to take from other people just because it’s available. I am not after money per se, it is just a reflection of what standards the person has for themselves. I haven’t met his family in person, although from all the descriptions I understand it is a ‘normal’ kind, and financially comfortable family which, as K says, may be OK supporting their adult son way into his adulthood. I haven’t discussed with him his family’s views on him having kids. Am I right in assuming I should just discount his ‘attempts’ to get the business off the ground – per common wisdom, we should choose based on the current situation and not based on projections and plans. And yes, he is a kind hearted guy and treats me well. He is just not a very practical / pragmatic guy from the looks of it. I just feel I will soon get too much of the dreamer side of his and of having to think about the day to day, financial security etc. So leaning towards ending things here…

@Angel, it sounds from what you’ve said like he’s just dabbling in being an entrepreneur and the likelihood of this business being profitable isn’t high. Sounds like he lacks direction and at his age that’s a major red flag. He just doesn’t have the drive or the skills or ambition to be able to support himself, much less a wife and a family. God help him if his family cuts him off. You don’t want to be his only source of support. Money isn’t everything and you don’t want to judge a man solely on money. But you are right to be concerned in this case.

So you were the one pushing for kids? I assumed it was him in your first post. I dont understand how you can engage with a man a year long and now suddenly ridicule him like this. He has been like this all along. I understand this is not your man if you feel like it. But if you are the one pushing for kids and suddenly waking up, i think you had big blindfolds on as well here.

Besides the mooching he also doesnt sound like a guy who wants kids if he frames it as: im not against it per se. That to me looks like a bigger problem than the mooching.

Thanks Lane. So he had started as an employee in his 20s and then, not liking a boss/structure and preferring to be his own boss, started his own business in early 30s, when he first got married. According to him, his wife never had to work, and they bought a house, then sold it and bought a bigger one etc. So far so good. Then in early 40s, he had health problems which led to the first business collapsing and his wife left him around the same time. House was sold to fund divorce and also fund an EMBA which was part of his earlier plans – so no property/money left as a result. Then, EMBA done and health issues sorted, rather than working to revive the old business and as you say, do whatever possible to get back on track independently, he chose to follow this ‘new business idea’ and hence allowed himself to be ‘temporarily supported’ by his comfortable family. They also support the ex-wife btw who is still not working (sorry! it sounds really bad…) Although I am not a business owner, I am a professional educated woman and see around me how businesses are run and what it takes. It took me a while to unravel all this, and tbh I had maybe naive hopes to wait for his plans to progress and become more concrete. It’s not that he does nothing…he does ‘something’. It apparently progresses but who knows if and when it will work out. As you say, my gut feel says at least 2 more years IF he works his b*tt off. It’s just getting quite exhausting for me to keep this internal debate on whether I trust his business acumen or not, if it will work out or not etc. I have my sh*t together so why would not he. I also had these rose blinds on thinking that if we get on as people it can go a long way and he can be this nurturing and kind force, supporting me emotionally etc. But I agree with all the posters that while the guy may not be a super alpha male type of career guy and earn less than the woman etc, it turns out that self sufficiency at a basic level must be the minimum. I just feel stupid as seem to have trusted some kind of ‘damage case’ where by mid life there is hardly anything accumulated but more lost or destroyed…. Big sigh.

@Angel… you’re never going to understand him so just let that ship sail. YOu’re trying to overlay your life paradigm onto his, which is entirely different. YOu’re into working and being self-supporting; he’s fine with his family taking care of him. AND they support his ex? And he didn’t have kids with her? YIKES. Why, if they sold the house and all the assets are gone from the marriage?? Who got all that money and where it go?? Or did he spend it?? Big red flags and disconnects in his story all over the place. I”m wondering exactly how successful that first business really was. Men who create one successful business don’t go out and do an EMBA and then roll over and let their family take care of them and let their ex sponge off his family too. It could take years for this new business to succeed, if it ever does. And in the meantime, he’s approaching his 50s fast. And what if he has “health problems” again??

This sounds like a big mess that doesn’t jibe with your values and lifestyle at all. You definitely do not want kids with him… he doesn’t sound keen and they aren’t toys for his sister and mother to play with. Take off those rose glasses and cut him loose. Plenty of men out there who are self-supporting and would be enthusiastic about having a child with you, not lukewarm “I wouldn’t mind.” This guy is too much of a soft beta male mama’s boy type for you to be happy with him long term.

Now he has to get a group opinion about his relationship with you, and told you what they said you should do??

And his family supports his ex-wife so she doesn’t have to work and they’re all best buddies????

Oh NO. Bye-bye. You can do much better than this.

I have a similar situation and just broke up. Only with me, there was never any prior success. He has been at it ” starting” his company for 8 years and has only ever made debt with it, that his parents pay for as well as all his rent, health care and living expenses. When he invited me to his parents house saying that when we drive around we could get lucky because his parents will pay for gas money, I have just had it.
There where many small instances that showed me that while he is a gentle nice guy, I can never live with a man like that. I wanted to go to a spa one day after a particularly stresful workweek and that spa is only nice in the morning, when it is reasonably empty. He thought getting up before 10 was an undue hardship and he could not manage to be at the Spa at 9 in the morning. That is when I noticed he never gets up before 10 or 11 at all and often just plays video games during the day. He hired tow other people on his parents dime to work for him via the interent, but as far as I could see, those guys where just ripping him off, dragging out the project to make as much money as possible. All the while he complained about his hard life. I am so glad I made it out quickly before I fell in love.