We Get Really Honest with a Young Woman Who Wants (a Lot of) Money From Her Older Man


QUESTION: How do I get my married, blue-collar boyfriend to gift me a down payment for my house?

CHELSEA SAYS: Wow, I don’t even know where to begin with this one. So I’m assuming you’re having a May-December affair with this boyfriend of yours, and his wife has no idea. I’m not judging the fact that it’s an affair—to each their own. But a down payment on a house is not like a new purse or a pair of shoes. That’s a lot of money, especially for someone who, in your words, is “blue collar.”

Unless him dishing out that kind of money was part of your arrangement when your May-December affair first started, or unless he’s mentioned that that’s something he’s willing to do for you, I really don’t think you can ask him to pay for your house. Don’t get me wrong, you can definitely give it a shot, but don’t be surprised if he refuses. And I really don’t recommend tricking him into it.

I’ll be the first to admit that a girl has needs, whether it’s financially, physically, or emotionally. If you’re not getting what you want or need out of this May-December affair, then maybe it’s time to end it and move on. Maybe try finding someone who can give you everything you want out of a relationship.


TRENT SAYS: Seriously? You neglected to say whether or not he and his wife have a new baby on the way, too.

If this is nothing more than a May-December affair, why should your “married, blue-collar” boyfriend give you a down payment on a home? Did he say he was going to? He’s married… and more than likely has financial obligations at home. And, in your words, he’s “blue-collar,” which probably means he isn’t in the top 1.0%. So, I’m guessing he doesn’t have a lot of disposable income kicking around to “gift” you a down payment. And I’m willing to bet that’s not exactly what he had in mind when he started this May-December affair.

The best way to get him to gift you a down payment would be for him to introduce you to his boss and get you a job interview. It’s the best of both worlds. You can spend more time together AND you can save for your dream home!



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