My (M31) refusal to pay off my sister’s (F31) debts is causing a big family drama

A successful entrepreneur (31M) finds himself at the center of a family conflict after refusing to pay off his sister (31F) and her fiancé’s $500K student loans as a wedding gift. What started as a celebratory dinner escalated into a heated argument, with his father pressuring him and making assumptions about his wealth. The fallout has left the sister considering eloping, and now the family is pointing fingers. Read the full story below.

‘ My (M31) refusal to pay off my sister’s (F31) debts is causing a big family drama’

This is kinda long and I know that asking strangers on the internet may not be the best way of working out what to do but I really need to get this off my chest. The first thing to say about my father is that he places a very high value on formal education. He had very little of it himself but believes that it is the best thing that you can do in life. I am one of a set of non-identical twins (with my sister) and she is everything that he could hope for in that she has a bachelors, a masters and has just completed law school.

Unfortunately for him (and me) I am not suited to formal education at all. I did enroll for one semester at a state u but I knew from Day 1 I had made a mistake and left. He was furious about that at the time and confidently predicted that I would be a b** and a loser for the rest of my life.

However, I found my niche as an entrepreneur and after struggling along for a few years at the beginning am now doing very well. In the same way that I knew college was not for me, I know that running my own business is. I have started and sold a number of them over the years and, although not everything I have tried has worked out by any means, the last one I managed to sell for a decent chunk of change (low 8-figures) and have recently moved across country to NYC to find a mentor to help me play in the big leagues.

Prior to this incident I thought that my Father had come to terms with me not going to college etc and making a success of being a businessman instead. He and I have never been on the very best of terms but I did honestly think we had managed to get to a sort of “working relationship.”

I should add that my sister and I have always been close and although our lives have taken us in different directions we still speak at least once per month. I always knew that she must have incurred a good amount of student loan debt over the years but I have never tried to tell her how to live her life and she has never tried to tell me how to live mine.

My sister got engaged last year to a guy she met in law school, I have met him once when they came to NYC for a visit and he seemed alright to me. Fastforward to two weeks ago and I am travelling from NYC to our hometown for a “meet the family” type dinner with my family and my future BIL’s family (coincidentally, they come from a nearby town). Upfront I will be very honest and say that I didn’t really want to go as it is a long trip for me, I am very busy and what does it matter if I meet his family or not? But I go, for my sister’s sake.

Anyways, just before dinner my father pulls me off to one side, tells me that sister and BIL have a combined student loan debt of nearly $500k (WTF!!) and it would be really nice if I “did something for the family for once” and paid it off for them as a wedding gift.

Frankly, I have been expecting him to ask me to contribute to the cost of the wedding and I had already decided that I would just keep my mouth shut and pay up so long as it was less than $25k, but this really shocked me. It was the really matter-of-fact way that he said it. Now, I have the money and wouldn’t really miss it but that was not the point.

It gets worse. As we are sitting down and eating it transpires that he has told everyone there that I am “rich” and I will be paying off the student loan debt. There are toasts and heartfelt thank-yous while I am just sitting there stunned at being railroaded in the most brazen way I have ever seen!!

Long story short, I said a few things I probably shouldn’t have and end up walking out of the restaurant there and then and going back to the airport and catching a red-eye back to NY. While I am in the air I am stewing on the whole situation but by the time I land I have calmed down and thinking “what have I done”? However, when I switch my phone back on in the cab back to my apartment it just blows up with voice messages and texts from my parents and sister. Later that night, my sister rings me again and this time I answer it.

I explain that it isn’t about the money but the way in which it was just assumed that I would pay up. I know that this sounds really petty now, but I was just so angry at the time. My sister was really surprised as she knew nothing about it before the dinner and afterwards dad was going round telling everyone that I had said I was going to pay it but had now changed my mind! She ended up being really embarrassed in front of her future in-laws (who are now wondering what their son is marrying into) so is now very pissed at our dad.

Now I come to the issue. Turns out my sister went back and confronted our dad about it and there was a huge row and now she is talking about eloping and not having a big family wedding at all or only inviting her fiance’s family etc etc. My phone is being besieged with messages from my parents to talk to my sister and ask her forgiveness so that she will forgive them. The final message from my father before writing this was just him ranting about how I don’t deserve the money that I have and it is because of “people like me” that college graduates are struggling. Seems that we aren’t in such a good place after all.

I am not sure what to do. Was I totally out of line? I don’t have many friends to talk to about this and those I do have probably have as equally skewed perception on this as I do. Did I get this totally wrong? Should I just have paid the money? I hate being railroaded and that is what it felt like, as though my only value there was a source of funds. Having said that. I’d hate to think that my sister’s wedding gets ruined because of me…

Tl;dr: I have made some money selling a business and my father thinks I should pay off sister’s and BIL’s student loan debt as a wedding gift and blows-up when I refuse. Family drama ensues, wedding in danger, parents blame me. Should I just have kept my mouth shut and paid up?

Here’s the feedback from the Reddit community:

CynicLibrarian −  You did the right thing. There is absolutely no reason that you should pay her debts, and if that is a condition of having a relationship with your family, it sucks that you had the misfortune of being born into a company of idiots. If it makes you feel better: you sound like the most grounded of all of them.

emilouwho687 −  I think it was super generous of you to consider offering $25,000 to pay for your sisters wedding. To me, that is already going above and beyond as a brother. Your father is out of line. Also, you’re lucky that your sister is also on your side. If she wasn’t, this would be really messy.

You don’t need to pay for your sisters (let alone your BIL!) college education. If you wanted to gift them anything as a wedding gift, that’s your prerogative. You need to simply let your father know that the only money he gets to decide how to spend is his own. Full stop. And it was wrong of him to try and trick you into paying by announcing it in front of everyone. You are owed an apology.

Goblins1432 −  Your father is trying to live vicariously through his children. The education he wanted was something he only experienced through your sister and so holds you in contempt. That is his problem at this point, not yours. Keep up with your sister, she didn’t expect you to pay and seems to recognize that what your father did was wrong. Her eloping is up to her and her fiancé.

If you want to help (that 25k is no joke even against 500k of debt) go ahead but don’t feel like their choices mean your own life decisions take a back seat. You worked for your money, they worked for their education, each came with its own set of consequences. Don’t let your fathers expectation hamper your success.

[Reddit User] −  Dude. Look at my post history and read the post on my inlaws expecting my husband and I to pay up for my BILs honeymoon. For some reason, my inlaws think we owe his brother a piece of our hard earned pie. We don’t and you don’t. I think your father is jealous of how well you succeeded without a degree and a lot of his identity was probably based on what he could have been had he been privileged enough to get a good education.

When you didn’t get an education and succeeded anyway you basically ripped that chip right off his shoulder. Your sister followed his advice and ended up in massive debt. I bet if your father had the means he would love to pay it, but he doesn’t so to redeem his own pride he wanted you too. This isn’t about you it’s about your father’s pride, identity and self worth. You did nothing wrong and I’m sorry you’re having to deal with this. Distance yourself from your father because it looks like he’s just waiting for you to fail.

YesHunty −  Here’s the thing. Your sister and BIL are GROWN ASS ADULTS. They decided to get the loans, they can f**king pay them off. That is not your problem. At all. For your father to even consider asking that is completely ridiculous. If he placed such a high value on her getting an education, he should be the one helping her pay the loans down if needed. You are her brother, not her damn parent. Your money is YOURS and its being rude how your father is acting.

F**k your dad. I feel bad for your sister too because he not only managed to tarnish your reputation, but hers too. If I was your sister I would elope and not include him in anything. I would let your sister know that your father did that without you agreeing to it in any way, shape, or form. If she needs help, she can ask like any grown mature person, and accept whatever the answer may be. Your dad has such a s**tty attitude. And after reading through your post a few times, I know its jealousy.

He obviously invested alot into education, pushed your sister to do the same, and then you wound up with more than he could have ever dreamed. That’s jealousy. Don’t let his jealousy and rudeness ruin your relationship with your sister. And DO NOT give any of them any money unless it is 100% okay with you on every level.

Bigassbird −  Your sister knows what went on and believes you. She should be able to smooth things over with her fiancé’s family. Aside from the fact that the money owed isn’t that much for you its a HUGE amount for most other families in this world. How the f**k have they racked up half a million of debt?

If you can, and you want to, then help your sister out on your own terms and just cut your dad out your life. You’ve done exceptionally well despite his influence and will continue to do so. Anyone who involves you in something this major without your permission should just be dropped.

Ren_san −  You are getting a lot of validation and psychoanalysis of your Dad but little concrete advice… I have some suggestions I think may help you and everyone move forward.
1. I think you need to arrange another dinner with your sister, future BIL, and his parents without the rest of your family. Apologize for the drama and enjoy a nice, relaxing evening. Don’t bring up your wealth or wedding gifts at all, and if someone else brings it up (I can’t believe anyone with any manners would) then change the subject.

2. Put yourself in the frame of mind as though your father will never know what you gave them as a gift, that you do not know about their debt, that they are eloping and will have no wedding costs. Then decide on a gift. It may not even be financial; that is fine. Maybe it is a large cash gift that she can put towards her loans, towards her wedding, towards a down payment… Maybe it is a horse. Or a honeymoon. Or a designer wedding dress. Whatever would make you happy to give her, do it, and don’t think about the other pressures when deciding.

Your sister is not a victim of her student loans. She signed every paper agreeing to pay back that money, and she was an adult when she did it. And if she chooses to have a large, lavish wedding, she is choosing to spend thousands on that that could make a large dent in her debt. The most important thing here? She knows all of these things, and expects nothing from you. Good for her. Your father has been analyzed enough here.

No matter how much wealth you own, you don’t owe anyone anything. Being wealthy and coming from a non-wealthy family, this issue often comes up. The question you have to ask yourself is, what level of wealth is it “okay” to start assuming family members owe you something? My brother and his wife easily make $100,000 more than me and my husband per year. But it would be apalling for me to expect them to give me money.

Yet, at some level of wealth disparity this problem always arises… The answer is never. It is never okay to assume you are entitled to someone else’s money. Period. And you should never feel like someone else is entitled to your money. That way, gifts can be given and received with joy, not out of obligation. So, give your sister a wedding gift that gives you joy to give her. And tell your father your finances are none of his business, and you will not discuss it with him further. Ever.

elephasmaximus −  This is all on your dad. He made his bed, he can lie in it.

parasoja −  That is so far over the line that I wonder if there might not have been some sort of mitigating factor. Just before dinner my father pulls me off to one side, tells me that sister and BIL have a combined student loan debt of nearly $500k (WTF!!) and it would be really nice if I “did something for the family for once” and paid it off for them as a wedding gift … As we are sitting down and eating it transpires that he has told everyone there that I am “rich” and I will be paying off the student loan debt … My sister was really surprised as she knew nothing about it before the dinner.

Did your father tell anybody before talking to you? When he said you “should” give them the money, did you say “no, I will not do that” or “I’ll have to think about that”, or did you just kind of not respond? If you didn’t respond, he could have taken that as assent. Obviously he shouldn’t have (very, very, very shouldn’t have) but there’s a huge difference between deliberate railroading and an honest – albeit thermonuclear – fuckup.

0928346234 −  You are absolutely right. This is a matter of principle. Your father pushed your sister to get the education (and the debt). This was his vision, his principle. Now he is trying to manipulate you into relieving your sister from consequences of his and her past decisions which proves that he was wrong all along and you were right. Don’t pay your sister debt. She has extremely valuable education. In 5-10 years she will be able to pay it in full while making 6 figures salary per year. She will not suffer by any means.

One of the reasons why lottery jackpot winners go bankrupt quickly is they keep giving money to their family and friends. Once you gift serious amount of money to somebody all other family members start feeling that they are entitled too: some nephew has serious medical condition, somebody got in accident, somebody opening the business and struggling – list goes on and on. Once you start giving your money away – they never stop asking and there will be even more of family drama.