Will he return my money?

A friend borrowed money from me many months back and hasn't returned a dime. I'd reminded him many times but I feel that he kept giving excuses (his clients delayed his payment, etc).

This is a long-time friend so I'm pretty upset with him + it wasn't a small sum.

Will I get my money back?

My sig + 2H ruler (Sun) are in opposition with his sig which isn't a good sign. Seems like we'll clash over this and I won't get my money back?

I'm in my 12H (bad position) combusted by Sun.

What does Sun/Moon/NN conjunct Asc mean?

Alas, I don't think this looks promising. Hopefully you have some kind of "paper" on the loan, even if in the form of emails or text messages. Otherwise the loan may be difficult to prove if you wish to take your "friend" to small claims court, or see if you can find a legal way like a lien to reclaim it.

When I was younger I also loaned money to "friends" who never repaid it, who changed phone numbers without telling me, and then dropped out of sight. I look at that lost money now as my tuition in the School of Real Life.

A friend is an 11th house matter, ruled by Venus. A friend's money is the 2nd house from the 11th, or radix 12th house. Alternatively we could look at your money as a loan (shared resource) as your 8th house matter. Either way, we see Venus (him) in the 12th house of deception.

You are symbolized by the moon, with its next aspect to a 7th house Saturn. I would consider this to be an affliction, suggesting nothing good coming out of the matter.

Both of your significators are combust. It's possible that he actually doesn't have the money to repay because he's mismanaged his finances.

No doubt you've suggested to him a generous repayment schedule, with a small amount owing each month till he's paid the entire sum.

However, if you have any documentation on the loan and if the amount was big enough, you might want to consult a lawyer on your options.

^Thanks, I also think there's a slim chance of getting my money back. Yes, I have all our conversations in text but I'm not sure if I wanna take him to court.

I believe he probably doesn't have the money to pay me so I've suggested he pay me back little by little, which he didn't do as well.

Like you, I might have to write this off as life lesson tuition fees.