<prompt> Human: My fiance has 100K in student loan debt medical school. I have 400K in savings mostly in index funds.Once we are married, I think it makes sense for me to pay off her student loan debt with some of my savings. Two questions here. How do I do this optimally? - Are there ways to optimize selling a large amount of index funds and using that money to pay student loans. - Are there certain deductions with caps that I should watch out for? - I have a large free cash flow 70K year from my salary, should I instead use that to pay for the debt instead of paying capital gains taxes? God forbid something goes wrong in our marriage, and we get divorced. Is there anything I can should do to protect myself in that scenario?  <response>: Boy this is a cynical group when it come to fiances. Maybe it is because I have been married 25 years but if I had 400K I would have helped my wife when she was my Fiance with her student loan if for no other reason than the whoopie was worth it.Depending on her interest rates I would pay it down with cash flow by adding extra payments. You would have to analyze if the Capital Gains tax and the loss of write off on SL interest is worth it.If you help before marriage I would sign an agreement that any assistance you provide is reduced on an X amount per year. This way if you pay all of it and no marriage you get it all back. If you get married and she bails after 5 you get a percentage back based on that scale. Maybe at the rate a standard SL repayment on that amount would be at a set time period.The last thing you want to do is wipe out all her debt and she leaves marriagerelationship with no debt just as she starts earning the big bucks.By the way get this in writing and just in case she is offended, wear a hard hat when you bring it up and make sure the sheets are clean for the couch. 