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Boyfriend Urges Girlfriend To Seek Half Million Dollar Loan From Wealthy Stranger For His Business Venture

by Jeffrey Stone
December 25, 2025
in Social Issues

A young couple from tough immigrant backgrounds scraped by, constantly stretched thin by bills and family obligations, until a glimmer of hope appeared in the form of a millionaire connected to the girlfriend’s elderly client.

The boyfriend, convinced his business idea would lift them out of poverty in months, pressed her to ask this near-stranger for a massive $500,000 loan, seeing it as their fast track to stability and more time with loved ones. She refused, calling it inappropriate and dangerous to her job, while he grew increasingly frustrated.

A young couple’s request for a massive business loan from a wealthy acquaintance sparked relationship tension.

Boyfriend Urges Girlfriend To Seek Half Million Dollar Loan From Wealthy Stranger For His Business Venture
Not the actual photo.

'AITA for asking my girlfriend to ask someone she knows for a loan of 500k to start off my business?'

My girlfriend (20F) and I (20M) come from a very poor background. Our parents moved to the U.S for a better life.

My partner and I are both first generations. We often struggle to make payments because of our background, we’re either making a big purchase or helping out family.

My girlfriend is a caregiver. The lady she has taken care of for over a year now has made a friend.

My girlfriend got to meet the friend and it turns out she’s a millionaire. My girlfriend told she was a millionaire because my gf thought it was cool.

I saw it as an opportunity to see if the millionaire was willing to give us a loan to start the business since I know it will be successful and...

however, my girlfriend sees it as us begging and asking for money as if the millionaire owes us.

My girlfriend thinks this is a handout but in reality it’s a loan that an average bank won’t give to anyone my age and that’s why I see it as...

Since the conversation I haven’t stopped thinking about it because I hate seeing my mom working night shifts

and I hate not being able to hang out with my family as much or my gf as much.

I see this as it’s either we wait 10 years if not more to barely be over the poverty line or we can be over in as little as 2...

EDIT: the lady my gf takes care of got 3k stolen from her. It was the “friend” that was a “millionaire” lol.

Chasing entrepreneurial success while juggling tight finances can feel like navigating a minefield, especially in a young relationship. This Redditor’s situation boils down to a hopeful vision versus practical concerns.

On one side, the drive to escape poverty through a bold business move is understandable. Many young couples from immigrant backgrounds face similar uphill battles with bills, family support, and limited access to traditional funding. He views the potential loan as a smart bridge over those barriers, believing strongly in his idea’s potential.

On the flip side, his girlfriend’s hesitation makes sense too: Involving her work connection in a massive personal request could jeopardize her job, which provides steady income they both rely on. It’s less about doubting his dream and more about protecting their current stability.

Motivations here stem from shared hardship, but they manifest differently. One leans toward calculated risk-taking, the other toward safeguarding what’s already working. This kind of mismatch isn’t uncommon in partnerships facing money stress, it often amplifies underlying fears about security and trust.

Broadening out, starting a business is thrilling but statistically challenging. According to the U.S. Bureau of Labor Statistics, cited in Forbes, about 20% of new businesses don’t make it past their first year, rising to around 50% by the fifth year. These numbers underscore why lenders, including wealthy individuals, are cautious. Success requires not just a great idea, but experience, market fit, and resilience against setbacks.

Financial expert Heather Boneparth notes on the pitfalls of money discussions in relationships: “You can love each other deeply and still allow money to erode your relationship if you’re talking about the wrong issues, or not talking at all.” This rings true here. Open chats about goals, risks, and boundaries could help align their perspectives without resentment building.

Neutral advice? Explore safer funding paths first like small business grants, bootstrapping with side gigs, or building a detailed plan to approach formal lenders or angel investors, who typically invest far smaller amounts initially, often $25,000–$100,000 per deal.

Prioritize her job security and discuss compromises, like scaling the idea smaller to test waters. Ultimately, team up on realistic steps. Many successful entrepreneurs start modest and grow steadily.

Here’s the comments of Reddit users:

Some people believe the request is fundamentally rude and presumptuous.

Kirin2013 − YTA. Just because her 'friend' is a millionaire doesn't make it right to ask them for a financial loan to start a business.

It's downright rude in fact. Plus, never loan money to friends.

Significant_Town_843 − This is one of the funniest posts ever. Hey rich person I barely know, can you loan me $500k?

Of course no problem let me get my cheque book. YTA 500k times over

Some people argue that the plan endangers the girlfriend’s job and professional trust.

Morganx27 − YTA. Asking the friend of someone your gf professionally cares for for $500k out of the blue is an inappropriate thing for her to ask as someone in...

If you asked, you would not only not get the $500k (nobody would give such a huge loan to someone with no track record,

you don't become a millionaire by giving away half a million every time someone asks), you'd probably lose the income your GF brings in.

I assume the person being cared for is vulnerable in some way, and your gf is in a position of trust.

To use that trust to potentially put a strain on the person's friendship is absolutely inappropriate.

[Reddit User] − I think you’re delusional, but I don’t think that’s an official verdict here so I’ll go with YTA.

It’s not even someone your girlfriend knows, it’s a friend of her client.

Depending on how the friend take the request and the stipulations of your GF’s work policies,

she could very easily loose her job over something like this. It’s insanely unprofessional.

AaeJay83 − Yes YTA. You're willing to put your GF job on the line for this. Truthfully, who will give a 20 year old a loan for $500k.

Did you even think this thru? If said person is a millionaire, they didn't get there making poor financial decisions.

What happens when this person tells GF boss about the request?

Some people contend that no rational millionaire would lend such a large sum to an inexperienced stranger.

Jujulabee − YTA And beyond that unless the "millionaire" is senile or an i__ot she is NOT going to loan you any money let alone $500,000.

Your GF is just going to embarrass herself and possibly ruin her relationship with her employer for even asking such a ridiculous thing.

People most likely wouldn't lend that amount of money to their 23 year old children let along a stranger.

DuctTape66 − YTA, there's a reason banks won't give this kind of loan to young people starting a business and the same reasons apply for the millionaire friend.

- You have no experience running your own business.

- The business runs every risk of losing all that money (yes, it does, no matter how sure you are, if still does)

- What the hell kind of business needs this much to start?

- You don't seem to even be planning to give this rich friend a pitch of your own or seem to have even tried to find a lonegiver on your...

you just want your gf to ask for a loan for you, and that shows how lazy you are: an indication you are not prepared for the work of running...

- You also state you want to hang out more with family and gf, starting your own business will not give you that...

Also indicating you do not understand the amount of work it will require from you to be successful.

My tip: take a business class and start out with something very small without risking loosing a lot of money and see how that goes first.

Then you can pursue the bigger dream if you still think it's what you want.

Some people criticize the OP’s lack of experience, unrealistic expectations, and poor business sense.

mathbabe7 − The fact that you think a millionaire will hand out 500K for a random 20 year old

AND that you think it's OK to make such an obnoxious request through your girlfriends risking her relationship with her employer

tells me everything about how much business acumen you have.

YTA Read more, educate yourself on interpersonal skills and business management, build a solid plan and you will find a way. Good luck.

[Reddit User] − YTA. More than half of all small businesses fail.

What experience and education does a twenty-year-old guy have to make you think you can run a successful business?

And expect an unrelated person to shell out half a million dollars into? That is a LOT of money to just hand over to a young, inexperienced person.

Don't even call it a loan because the reality is that the person will never see that money repaid.

It's her money, nobody else's, and you aren't entitled to any of it. Listen to your girlfriend.

Work your way up, polish your job skills, get some training or education. Stop with the shady get-rich-quick schemes.

LostDogBoulderUtah − YTA If your business plan was any good you'd be reaching out to angel investor groups or pitching it.

Actually, if it was really good, you could start the basics of it and angel investors would be looking to find you. I had that happen.

Shot the breeze with a professor and showed up to my next class to find he'd brought ten potential investors to hear my elevator pitch.

It fell apart as I tried to do business with family instead, but I learned a lot.

Just because this person has money does not mean that they are eager to hand it out or be a piggy bank.

If a bank thinks you're too risky, why would this person be willing to loan you money?

You're high risk with a low chance of success. No experience in management or even working in a business. Also... half a million dollars is a crazy sum to ask...

You can open a number of franchises with that, but most businesses start with less than $5000 of capital.

And you want to start a business to have more free time? That's not how it works.

You'll work 80 hour weeks for at least the first 4 years just to get it running.

Worse, if you can't manage finances and hard choices and not giving money to relatives when you don't have the money to give?

Well it doesn't get easier when you do have the money in an account and they know it.

It's really easy to wind up bankrupt with incredible debt. Or worse if you deal with the wrong people.

In the end, this story reminds us that chasing dreams shouldn’t come at the cost of trust or stability, especially when a surprising twist revealed the “opportunity” was anything but reliable.

Do you think the Redditor was wrong to push for the loan request, given the high stakes for his girlfriend’s job and the slim odds of success? Or was his frustration understandable in the face of ongoing financial strain? How would you balance big ambitions with protecting your relationship? Share your hot takes below!

WHAT DO YOU THINK OF THIS STORY?

WHAT DO YOU THINK OF THIS STORY?

OP Is Not The AH (NTA) 0/0 votes | 0%
OP Is Definitely The AH (YTA) 0/0 votes | 0%
No One Is The AH Here (NAH) 0/0 votes | 0%
Everybody Sucks Here (ESH) 0/0 votes | 0%
Need More INFO (INFO) 0/0 votes | 0%

Jeffrey Stone

Jeffrey Stone

Jeffrey Stone is a valuable freelance writer at DAILY HIGHLIGHT. As a senior entertainment and news writer, Jeffrey brings a wealth of expertise in the field, specifically focusing on the entertainment industry.

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