I'm dating a divorced guy and we're talking about getting married and maybe having a family. I love him but he's paying a lot of alimony to his ex in another state. His ex is living with a guy but has no intention of remarrying because she likes the money. I hate to be shallow, but practically speaking, my boyfriend has a financial millstone around his neck that could be there indefinitely. And that makes it feels like there are three of us in the relationship. I'm not sure I should sign up for this.

He Said: If your boyfriend hasn’t talked with an attorney recently about the situation, he should. Laws on spousal support vary from one state to another but the trend most places is away from permanent alimony towards a “rehabilitative” model where the person receiving alimony uses the temporary support to prepare themselves for financial independence. Also, in many states, living with a partner is grounds for forfeiting your alimony.
 
But there may be more at stake here than just money. You said that it feels like there are three people in the relationship. While sounds difficult for you, it’s not unusual. People’s lives can be astonishingly complicated by multiple financial obligations: child support, aging or disabled family members, private school and college tuition, student, business, personal, and co-signed loans, bail bonds, credit card debts, charitable donations, mortgages, prescriptions and other medical bills, and on and on.
 
You say hate to be shallow. Then don't bet. If you love your man enough to get married and have a family, focus on making that successful and not on the money that is legally required to go to his ex.

She Said: I'm going to put this question in a category I see a lot. The category is called, "I knew from Day One that my partner had X going on, and now I'm months or years into it and I'm not sure I can handle X." How has he handled money up until this point? Does he pay his way or depend on you? Does he have savings or does every penny get used up by the "Laziest Ex in on the Planet?"

My guess is that you can indeed handle your man's financial obligations to his ex, and my reasoning is the fact that you've been handling it up until now. True, once you marry, buy a house, and have kids, his financial responsibility to you and his new family is going to increase, possibility creating a strain if he's still paying alimony at that point. But I too, find it hard to believe his ex can just keep tapping him for alimony for an indefinite amount of time. He needs to get aggressive about weaning her from his wallet.

There's also the other side of the coin. If you marry, you will be contributing to the household as well, right? (Unless, that is, he has horrendously bad taste in gold-diggers.) You two will be a financial team, and your own hard work, personal savings, prudent spending, and wise retirement investing will help make up for any alimony he's still paying in the future. Right? Because that's what marriage is--a partnership in which you team up with the goal of helping the other person, a situation in which you stop asking yourself "What's in it for me?" and start asking yourself, "How can we, as a team, make this work?"

Marry him only if you can see yourself moving from the first question to the second.