My [27F] boyfriend [29M] won $40k, now is in financial trouble. Should I help him?

My boyfriend (29M) and I (27F) are in a bit of a mess and I could use some outsider perspectives. About six months ago, he won big at the casino, around $40k. We were over the moon! He splurged a bit, got himself some cool stuff, and was really sweet to buy me some pretty lavish gifts too.

The issue is, he wasn’t aware that he needed to set aside money for taxes on his winnings. We’ve just been hit with the reality that he owes a hefty sum in taxes, and if he can’t pay, he’s looking at having to sell his car among other things.

He’s asked for my help to cover the tax bill, either by loaning him money or finding some other financial solution together. I’m torn. On one hand, I want to help him because he’s my partner and I love him. On the other hand, it feels a bit unfair since it was his decision to gamble and then spend the money without considering the consequences.

Should I help him out financially? Or is this a moment where he needs to figure it out on his own to learn from it? Any advice would be greatly appreciated.

TL;DR: BF won $40k gambling, spent it without setting aside money for taxes. Now he’s in financial trouble and asking for my help. Should I help him or let him sort it out?

original post here.

Advice

This is indeed a tricky situation, and it’s understandable why you might feel torn about how to respond. Helping someone you care about when they’re in a bind is a natural impulse, but it’s also important to consider the long-term implications of your decision, both for your relationship and your personal finances.

Here are some points to consider as you decide the best course of action:

1. Financial Partnership: How entwined are your finances? If you’re not living together, sharing bank accounts, or otherwise financially committed, it might be premature to take on his financial burdens. However, if you have a deeply intertwined life or are planning a future together, supporting him could be seen as an investment in your shared future.