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Man reveals to his fiancée that he won the lottery 5 years ago. UPDATED

Man reveals to his fiancée that he won the lottery 5 years ago. UPDATED


Money can often truly change people.

This story comes from a man who was hoping he had found true love, but he wanted to be sure. He loved his girlfriend and he knew she loved him too, but he was worried about telling her his secret. He was incredibly wealthy. 5 years earlier, he had won the lottery. He kept living their life together as though nothing had changed. Then, he shared the news.

[No Regrets] I won the lottery 5 years ago and haven't told anyone. I just got engaged.


So after taxes my winnings came to just shy of 4 million. I paid off all my debts, hired an accountant, fixed some things on my truck, and put most of it in savings. I kept my job, didn't move, and kept my mouth shut.

My family and I do not get along, for a number of reasons. I decided not to say anything to them because I didn't want them hounding me for cash. They made their choice about their relationship with me long ago.

I've been dating a girl for about 3 years now and recently asked her to marry me, she said yes. I bought a modest ring, just over what people would expect given my known employment.

This weekend I'm going to lay everything out for her and I can truly know she's in it for me and not the money. It's going to liberating to be able to buy what I want and take care of my friends, totally worth the wait

Here are the top comments after the initial post:


'take care of my friends'

Easy on this or you'll make them dependent.


Good on you man. I've always fantasized about helping out my friends and family anonymously if I won the lottery. Like, there's got to be a way to secretly pay off someone's student loans, right?

That way I can help out the people I care about without letting them know my situation. I know from experience that things like student loans and credit card debt from when we were all younger and dumber can sometimes feel like the only hurdle between constant stress and a normal, relaxed life, and I'd love to help my people get that relief if I got it too.


Be careful man. Money changes people.


Hey! Congratulations man, you're living the dream! My boyfriend has a fully laid out plan if he ever wins the lottery. I buy him his tickets every month because the state we live in doesn't sell them and I visit a neighboring state that does on a monthly basis. Although all the travel is killing me and I want to put a stop to that sooner than later. I personally think it is absolutely adorable of him, hope is a powerful thing.

Firstly, it seems like you have your head screwed on straight. Which is EXCELLENT! I have a decent fortune myself or rather my father does, but he's done a lot for me. Which brings me to my second point, my dad has always wanted me to have a prenup no matter what. So I know a bit about them.

With the prenup you will BOTH need INDEPENDENT legal counsel for it to be 100% verifiable/legitimate! If you pay directly for her legal counsel, then if you ever end up divorcing each other, I believe she can come back and say she was coerced/forced into signing it and therefore it isn't valid.

So, do not give her lawyer fees in any kind of traceable way and DO NOT pay her lawyers directly. Instead either hand her cash for it or buy her a material item that is approximately the same price as her lawyer fees.

Thirdly, as far as paying off your friend's student loan, feel free to do that! That guy sounds like he really deserves it for being good to you. I would encourage your friend to keep his trap shut about it though. Like, 'If I do this, this can't get back to my family...'

Finally, don't be surprised if your girl feels 'lied' to or whatever. You know her well so approach the subject with caution. It might be a big shock for her. There's always the eensy chance that this news ruins your engagement or makes her refuse to sign a prenup... if that is the case, man I'm so sorry, but she isn't truly the one.

However, with you two being together for 3years I highly doubt this will be an issue. You know her best so you will know exactly how to best approach it. In any event, I hope that was helpful/useful information. Good Luck and wishing you all the best!

The OP responded in the comments to concerns that readers had regarding his relationship:


Well this spawned some serious discussion so I'm addressing a few things:

  • We've already talked about prenups several times and are both for them. She makes enough to support herself and we're both financially independent of each other.

  • I do plan on offering to pay for any legal fees if she wants council on the prenup.

  • I have helped a few friends with small things financially, most have paid it back.

  • No, you can't have a dollar

  • For those of you who feel entitled to know the financial ins and outs of your SOs life while dating, that's your view. We're both adults who had careers prior to dating and have never needed to get into what is in our accounts short of 'Do you have this half of that bill?'. I've never told her I'm loaded, or broke, or gone over what my portfolio looks like because it hasn't come up and I'm fine with not knowing hers.

  • I do enjoy my job and the people I work with/for, so it's been easy to stay on. My returns net me about double my salary so I've been saving quite a bit.

  • I plan on buying a new vehicle, her as well if she wants one, a house, paying off a friend of mine's student loan (more on that), and taking some time off to travel.

  • A good friend of mine reached out to me early on and let me stay with him for close to two years, rent free, while I kicked a drinking habit and got on my feet. He's the only one I'll be pouring any kind of cash to and it couldn't go to a better person. He has a newborn daughter that will get a college fund, I'm paying off his school debts and his house.

Other than that, ask away boys 'n girls. I'll update everyone after dinner Saturday if you're still interested.

The OP then provided an update two weeks later:


I received a lot of feedback on my post and several people expressed interest in the outcome of revealing my finances to my new fiancee after keeping her in the dark for so long.

So, my plan was a relaxing evening on the odd weekend we both manage to be free from work or other plans. We went to an early dinner at one of our favorite Italian places (an inexpensive little diner nearby with great appetizers), and then finally went to see Star Wars. After the movie we grabbed some beer and wine for the evening and went home to relax.

Skip the weekly small-talk about work, friends, and the accompanying few drinks in and I told her I wanted to be open about everything with each other leading up to the marriage.

She got kind of quiet, a little guarded and said 'Well yea, so do I', pausing with that look people get when they want you to keep talking.

I told her we were never truly going to have to worry about money, that she could do whatever she wanted with her job or stay at home or change careers, anything... because I had north of 3 million dollars in the bank.

Her response was the slow 'What are you talking about? How?' kind of thing. I got up and pulled a financial statement I'd printed out and stashed in the coffee table drawer, handed it to her and told her I'd won it all a couple years before we met.

I kept it hidden because I didn't want my family hunting me down, that I didn't want people around me to change or to lose my friends.

Then she started apologizing, saying she should have told me before I proposed. She has about $40,000 in student loan and credit card debt and thought that was going to break the engagement.

She thought I was so financially responsible that there was no way I'd take on that debt because she never told me about it. It's why she'd been so open to a prenup in the vague conversations we'd had about it before, why she'd never brought up or talked about money.

So, after a long... long conversation about openness and trust (even mentioned some of you cynical bastard's opinions) we hashed out some ideas on what we would agree on for the prenup in regards to premarital debt/assets and all that.

I'm going to pay her debt off after we're married so the tax issue is less of a concern and all of my winnings will remain mine should we divorce, interest and dividends will be marital assets.

All told I'm very pleased with how things played out and we're in a great place for it. We're working with attorney's and my accountant this week and I'll be putting my two week notice in at work. She wants to keep her job but will request some time off so we can take a vacation and settle in to actually enjoying some money.

I talked my friend about paying off his house and all that, he very firmly refused anything for himself but was very grateful for the offer to setup his daughter's college fund. I'm going to keep leaning on him though, I think he'll come around to accepting some repayment of the kindness he showed me. Maybe a vacation at the very least, I dunno.

That's all folks, I'll check in from time to time if you guys have any questions, Happy Monday![No Regrets] Still!

Here are the top comments after this final update:


A positive lottery story? Awesome


This is absolutely the amount of money that could ruin your life. $3m isn't actually 'F you' money unless you're very careful. Especially if your family is a rat king of dirt bags.


I’m glad they both wanted to talk about their financial situation and wanted to give the other person an out if they felt like it was too much.


I feel like 3-4 million is not actually enough for both of them to not work (I know she didn’t quit but he said she could) and pay off friends’ houses and stuff like that? Especially if they are having kids? Kids are expensive, plus college, plus weddings, etc. My personal quit everything number is higher than that and I’m almost 50.


OP has a good head on his shoulders. It's so nice to see someone behaving sensibly about a lottery win, instead of blowing it all in a year and ending up bankrupt, which seems to be the more common story. Or maybe they're just the ones we hear about.


This is a happy update! So unlike most posts in this subs. Hopefully, we don’t jinx it.

So hopefully everything works out for this happy couple. Has anyone known anyone who came into a cash flow like this? How did it turn out?

Sources: Reddit,Reddit
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