Should I help my boyfriend get out of debt?

I have been with my boyfriend for a year and a half. We are in a serious relationship, leading to living together in the future. We’re both in our early 50’s, divorced, older teen kids. As part of my divorce settlement my marriage home needed to be sold and I received a nice sum from the sale. I’m planning on using a large chunk for a down payment on my next residence. I’m currently renting an apartment and want to buy a condo. I will still have a nice amount left after the down payment. My boyfriend is in debt and wants to pay off all his debts, credit cards, etc., which will total about $ 25,000. He didn’t want to have to ask me if I could help him out, but he did and he wants to work out a repayment plan of putting a certain amount of his pay check into my account monthly. It will take about 5 years for him to repay me. He is willing to sign some sort of an agreement. I seriously doubt that he will not pay me back. What are people’s opinions of me lending him this money?
to answer some of your questions – neither of us wants to get married again. We had been in long term marriages before. I also don’t want to give up my alimony. Living together is a commitment, we just feel that we don’t need that piece of paper.

A couple of you mentioned that he should see a financial counselor. How do you find one? And how would you know if that financial counselor is a good one with good advice?
As far as me putting into an investment, probably for retirement – I do have a nice sum in a couple of retirement accounts. Actually this money is part of the money to be used to “hide” so that I will be able to contribute as little as possible for my daughter’s college education. She does not want anything to do with me so I feel I should not be obligated to have to pay for her college.

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