Dating a guy for his moms money

Hi Meredith,

I am from Colombia and have been living in Boston for two years.

I have been dating my boyfriend for almost six years. He is a loving and caring person. We live together.

He is a son of a single mother who lives in a little town in Colombia, and I have seen her about once a year since we started dating. I once spent a week in her house and I realized they are different than my family in terms of education. I thought it might not be a problem as long as the they share the same values, but here comes the problem: I learned from my boyfriend that she used to be a compulsive gambler and lost all of her savings at the casino. But according to him, she went to therapy and she has not been playing for the past year, in part because casinos were banned in her town.

The last year she and her sister came to visit us in Boston. The sister told me in a casual conversation that she sometimes goes to casinos. I told that to my boyfriend and he felt uncomfortable and said his sister (who is married and lives next to the mother) told him it hasn't happened more than once and she is completely recovered from the addiction.

His mother is retired and has a retirement salary, which in Colombia isn't much, but she lives in her own house and doesn't have many expenses. But she is continuously asking him for money and I know he gives her some (I don't know how much and he doesn't like me to ask). We are a very young couple just starting in a new country. We have entry-level jobs and very little savings. We are unable to have dependents at this moment.

I really hate to be that person who is monitoring how their partner is using the money, especially if it goes for his family.
Recently, he asked me very casually if I would marry him and I said yes. Since then, I can’t stop thinking about this issue. If you marry someone you marry his family too. I am also afraid of the possibility of bringing her to the US, since we are planning to establish here. I asked him that and he said "no way," but I am not convinced.

What do you advice to deal with this situation? Would you marry a person with these family issues?

– Unsure About Forever, Boston

You must have an honest talk about how much your boyfriend gives his mother and how that affects his ability to pay for his life. Explain to him that you need transparency if you're going to get married. You have to hear the facts, talk about them, and then make peace (if you can) with each other's financial philosophies.

The best way to deal with this is to meet with a financial advisor who talks to couples before they get hitched. Let a third-party expert help you come up with a plan for your finances, one that includes individual expenses (his mom, etc.). It's so much easier to talk about the what-ifs with a professional. There's no need to deal with the tough questions on your own.

Readers? Can she marry this guy if she’s worried about his mother? How do you deal with similar issues in your family? What should she do?

– Meredith