Woman's BF Wins Lottery And Wants To Help His Ex-Girlfriend, And Current GF Worries What It May Stir Up

A few bucks can't hurt. right?

Redditor u/FarRush1 has a quandry. Money always leads to trouble if you're not careful. It can cause issues you've never even dreamed of. For instance.... My [24F] boyfriend [26M] won a lot of money, wants to help his ex.

My boyfriend won a lot of money in our country's lottery. We've been together for 2 years. When he first told me, after the excitement had settled, I realized this was his money. And wondered if he was going to leave me. He made it very clear he has no intention of leaving me, and that this changes nothing between us.

He first wants to focus on helping friends and family, and then being smart with the money, and not drastically changing our lives in any way. I totally agree and respect this. We were talking about people he wanted to help out, and he brought up his ex girlfriend that he dated from 17 to 22. He says he only wants to pay off her student loans, and doesn't plan to rekindle any sort of communications with her. She was there at a weird time in his life, low self-esteem, teenage stuff. And that she was the first person to ever really love him. They ended mutually due to job offers in different cities. I am fine with him paying off her student loans, but can't help feel a little uneasy in the feelings it could potentially bring up. He obviously still cares for her, and possibly loves her. And I would obviously never try to convince him not to pay off her student loans. It just feels like if he does, they're going to reconnect and I'm going to lose him.

He's the most caring, funny and sexiest man I know. I was completely in love with him, and fully intended on spending the rest of my life with him, before he came into this money. He could give it all away, and my feelings for him wouldn't change at all. I don't want anyone to think I'm scared of losing the money more than losing him.

Sharing is caring. NO?

Hush up! 

He needs to keep his mouth shut about his winnings. Please see this survival guide for more information about what he needs to do to survive the incoming storm.



Stop listening... 

So you can probably ignore 99% of the advice here because they're mostly focusing on how lottery winnings can make you dumb and try to help everyone.

Without knowing amounts, I'll tell you this - it will not rekindle their flame, and if this is a worry you should likely keep it to yourself. Let him help the people he wants with this money as long as he's being smart and saving enough for his future.

I gave about a third of mine away to family and friends, about 14 people total. 3 years later I've made that all back.

If he's smart, and listening to advice in those articles, the only issue you really have is that he's giving money to his ex girlfriend. You're going to need to swallow your pride on this and let him spend it how he wants, and trust him when he says he chooses you over her.


It's not the $$$

The money will directly connect them and create that situation. It most certainly does have to do with his handling of money.


Hide your coin! 

Nobody here really has experience with coming into a fortune unexpectedly. There's a reason why lottery winners are mostly broke. After they win the lottery.

He needs to put the brakes on all of that talk. On helping his family and friends. Of course, he probably already messed up by talking about it and suggesting this to his family. If he hasn't, he shouldn't. There will be one or two who will feel entitled to that money and get extremely resentful if he does not keep giving.

He needs to keep this information on the lowest of downs.

He needs to get to an accountant or other some sort of financial planner immediately.
Get his, and only his, debts settled. Blank the slate.
Get that money into some sort of investment strategy where he can get paid from the interest being made off of it rather than the principle.
If there's not enough money to get a comfortable living wage from the interest, just leave the money to mature as a guaranteed retirement fund.
If there is some principle left, sure, take a vacation, maybe help out someone. But still, he probably does not have enough money to both help everyone he wants and not have to worry about money any more.


The more, the unmerrier... 

It turns out that people who win the lottery tend to continue to manage money the way they did before they won. So if they were decent at managing money, they will continue to be. If they are spendthrift, they will spend it away.

If they're smart they set up a trust or other device to keep some of the money away from their own loose hands. I hope he does that.

I would be most concerned that his ex will figure out he came into a bunch of money and she, or her family and friends, decide to come after him for it.


Be safe...

IANAL. He needs to set up a trust, so he needs to see a financial advisor and an estate/probate attorney. Really push him to do this. Trusts also can help in lawsuits, since they're really hard to break (at least my grandparent's is). Again, I am not a lawyer, nor a financial expert.


Call Oprah. She'll know what to do. 

It sounds to me like he wants to do something nice for someone that was there for him during a rough period of his life.

Other than wanting to pay off her loans (which he could do through a lawyer and stay anonymous, no need to contact her at all) is there a reason to think he has feelings for her?


She single?

Is she in a relationship now? If so, has he considered it might throw a wrench into her relationship? I mean, I don't know how her significant other would feel about some previous lover of hers giving her a gift of cash, but it seems like it would cause friction there.


The past is the past! 

He seems a decent person from what you write.

He wants to do a good and kind thing for someone from his past. This is generous and incredibly kind, probably a 10 year jump start on fiscal stability.

If this "rekindles their love" then he isn't for you. If you aren't secure in your relationship or in his intent, it is better to know sooner rather than later that it is less stable.

If you choose to ask him not to do this, you may stir some concern and resentment on his part.

Youthful relationships are such a major part of our development into the adults we are going to be, he likely has several motivations for wanting to do this.

I support his desire to do this. What I might suggest, however, is the Daddy Longlegs thing, set up a blind grant so she gets the bill paid but doesn't know from whom, so it doesn't feel like charity. That won't work if his good fortune is public knowledge.


Do you trust his love?

You said that after he won the money, you felt scared that you were going to lose him. Why is that? Would you say that, money or no money, you both had a secure and loving relationship?

I think that might be the key to the problem -- how secure and loved me made you feel and how he feels about your before he won the money.

In my opinion, your best bet would be to just be open and honest with him about this, and calmly explain that you feel a bit uncomfortable about his idea. Without turning it into an argument, perhaps ask him how he would feel if you wanted to pay off an ex boyfriend's debts if you had won the money?

And I know this is far from the most important bit, but I do hope he is generous towards YOU with his winnings as well. Good luck.



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