Dating a Trust Fund Baby

posted 6 months ago in Relationships
Post # 32
458 posts
Helper bee
  • Wedding: April 2018

CapitolBee :  Honestly, 6 months in is too early to need a boyfriend to change things about himself.  

I couldn’t marry a person in his position who is not working and just partying all the time – but that doesn’t mean his lifestyle is wrong.

If he get’s a job or ambition or something FOR YOU then he will likely end up regretting it. 

I would just have some fun with it and keep it casual, don’t move in together or anything.  If he sorts himself out on his own then great, if not it sounds like your lifestyles aren’t compatible. 

Post # 33
861 posts
Busy bee

CapitolBee :  I too am jealous of your boyfriend! I could easily spend winter and spring snowboarding. I’ve known a few outdoorsman who were trust fund kids. Most of them found side work doing something they loved recreationally. Could your boyfriend pursue ski instructing in the winter, and possibly wilderness guiding in the spring and fall? Maybe he needs to find something he loves. We should all be so lucky, and if he’s financially set for life, I say good for him! There’s no shame in that. 

Post # 34
901 posts
Busy bee
  • Wedding: January 2019

Sorry but this is crap. I’m not quite a trust fund baby, but my parents have given me a lot of support. I still work a full time job, and a pretty selfless and thankless one at that. The problem isn’t his trust fund, it’s his attitude. His parents allowed him to be lazy and lack drive, the money isn’t the problem, it just limits his need to grow beyond the limitations of how he was raised. Yes I could date a trust fund baby, but no I couldn’t date a lazy money leech. Therapy is not an excuse either, plenty of working people attend therapy.. and GASP… have a job. He doesn’t need to have a high paying career but he needs to do something productive with his life, or I sense your frustrations will grow rapidly.

Post # 35
724 posts
Busy bee
  • Wedding: February 2020

To be honest, it does sound potentially like a compatibility issue more than anything. Unless he himself is venting frustration about his lack of career advancement, it sounds like he is perfectly fine with his leisurely life. And hey, if he has the means, more power to him!

Not everyone is ambitious or focused on advancement. And while that is fine, it is equally fine for you to realize that you want someone who has bigger goals than living a relaxed life. 

Post # 36
7002 posts
Busy Beekeeper
  • Wedding: September 2012

It sounds to me like you guys just aren’t compatible. You can like someone a lot but it doesn’t mean they’re the right person for you. At the core you just seem to have a different outlook on life. It doesn’t make him wrong and you right, or you wrong and him right – it just makes you different. 

You can ask yourself if you can “get over” his lifestyle and lack of ambition to find a career but odds are even if you try it will eat away at you. I agree with others who said 6 months in and you’re already questioning his traits? He’s not the guy for you, just be glad you realized it early and not a few years down the road. Find someone equally matched to you. 

FWIW, I don’t think there is anything wrong with him. He is who is. Everyone has different prorities in life. Some people prefer to work “easy” jobs and then travel cheaply rather than work the rat race with 2 weeks of vacation every year. Does that mean they don’t have drive or ambition? No, it just means they want different things in life. 

Post # 37
923 posts
Busy bee
  • Wedding: City, State

If you’re only 6mos into a relationship and you don’t like the way a man handles his personal finances/ career, why not go find someone you do approve of? I don’t think you’re in any position to expect that a man change his perspective on money. You’re dating. Relax. A man who works isn’t hard to find, if that’s what you value.

Post # 38
10687 posts
Sugar Beekeeper
  • Wedding: City, State

CapitolBee :  

Personally, I’d be fine with a Trust Fund Baby. They were my tribe growing up.

How old are you both?

What comes relentlessly through, Bee, is that you really need this guy to be someone else.  

Your family’s input really ought not be a controlling factor. Hearing them out in a respectful manner, sure.  But, internalizing their opinions?  Part of adulting is getting out from under the sway our parents hold over us.

Post # 39
2217 posts
Buzzing bee
  • Wedding: October 2019 - Chateau Lake Louise

CapitolBee :  So actually, this exact situation. 

When I met FH he wasn’t working, and hadn’t been for about a year. I didn’t really question it because he talked a lot about how awful his last job had been (it truly was) and that he was living on some money he had saved to buy a sports car. Ultimately he decided his mental and physical health were more important than the car and quit. It was an amount of money that, given his relatively modest lifestyle (he owned a small condo and had a roomate, along with cars which were paid off) it made perfect sense he wasn’t in a financial bind OR in a huge hurry to find another job.

But as time went on, and I found things out about his family – like that they own a hotel – and met his parents, it became clear he had some income from that source. He was pretty circumspect about it, because he had bad experiences in the past of people using him when they found out. 

Personally, I didn’t care about his resources insofar as where they came from. He managed them wisely and clearly had his shit together. We dated for about 6 months before he ended up getting another job. One that, I will admit, I found for him. 

In his case, it wasn’t laziness or lack of ambition so much as inertia. He legitimately had trauma around his previous job. It had him putting in 80+ hours a week and was physically taxing to the point it was damaging his health. He wasn’t sure what he was going to do in his next job, but dreaded having a similar situation come up.

Once he stopped working he spent his time off dirt bike riding, taking motorcycle trips, and generally catching up on all the amusements he never had time for when he was working.  He knew once he started a regular job, he wouldn’t have any time off for a while, and wanted to make the most of it. 

I also started to see signs of depression in him. A lot of his self-worth is tied up in being successful at work. Absent that source of affirmation, he got more and more down on himself. I eventually started sending him job listings saying things like “Oh, this looks interesting.” and “Have you thought about doing something like this?”

He landed in a job he had done in his 20s, but that it hadn’t occurred to him to pursue. He’s done very well there and his confidence has rebounded. 

I think knowing the underlying motive for your BFds behavior makes a lot of difference. Why he left his last job, what might be keeping him from actively looking for another one. Is he really content to just coast indefinitely, or is he feeling defeated and doesn’t know how to articulate that? 

If the former, then I think you have a fundamental incompatibility. You are clearly a do-er and have drive to accomplish things. If he isn’t similarly inclined, you’ll spend your entire relationship feeling like you’re pulling dead weight on a sled after all the snow has melted. You’ll both be unhappy; you because he’s dragging you down, and he because he’ll resent your constant pushing. 

If the latter, then I would try to think of ways to support helping him find something worthwhile to do with his time. Suggest some new or novel lines of work he could pursue. Suggest he get a job at a ski resort if all else fails; they need maintainance crews and office staff, after all. Encourage him to continue therapy, and to discuss his employment situation in the context of all the other things he is working through. 

Our culture tends to put a LOT of emphasis on employment as a source of self-worth. While I find that unfortunate, there’s no getting around it. He may not realize just how much not working is impacting his mental health. His sense of independence. His self image as a capable effective adult. 

However, if that just isn’t the case for him, and he’s just more of a go along to get along guy, you’d both be better off finding someone more in your own mind on the issue. 

Good luck

Post # 40
1097 posts
Bumble bee
  • Wedding: September 2017

Has he considered finding a job linked to his recreational hobbies? He could manage a ski lodge or a summer camp or something. If I had the funds to not have to work for a living, I think I would invest in becoming really good at a hobby or something I enjoy and see if I could turn it into a profession, even if not a lucrative one – like baking for a cafe or working at a vineyard or something. 

Post # 41
3400 posts
Sugar bee
  • Wedding: January 2021

It’s sounding more and more like you basically want him to be someone he’s not.

You shouldn’t get into and continue a relationship with someone who you are hoping will change.

He isn’t the person you are looking for, so why not free the both of you up to meet better matches?

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