I've been seeing a man for several months. He has gobs more money than I do, which is fine, but I am uncomfortable when he offers to pay for expensive things I could never afford on my own (i.e. airfare, hotel rooms, iPods). I keep resisting these offers, and he keeps insisting he doesn't at all mind paying for me. At what point in the relationship is it okay to start accepting big gifts from him without thinking of myself as a gold-digger?

He Said: This is actually a not-uncommon circumstance in SF, where that cute guy you met at the bar last night might turn out the latest Facebook or Zynga gazillionaire. Obviously, communication is the key. You have to judge whether this guy is mature enough to not allow the financial imbalance to affect the way he treats you. Grill him on this matter. Make him promise that he won't resent you for accepting his generosity, or hold it against you when you decline. This still will be difficult to gauge, as money has an insidious way of warping interactions of even the best-intentioned souls. Having been on both ends of this equation, I have developed a simple rule: Never accept or give anything material that might end up on eBay one day. But go ahead and enthusiastically enjoy travel and entertainment, which is by definition perishable and creates once-in-lifetime opportunities to deepen your bond and life experiences at the same time.

She Said: Asking yourself if you’re a gold-digger is a lot like asking yourself if you’re losing your mind. If the question interests you, the answer is probably no. And if you’ve been seeing him for several months, I’m assuming you’ve already had sex, so he can’t be trying to buy that. So with those two concerns aside, it’s time to ask yourself if this relationship has longterm potential. Can you see yourself possibly living together or marrying? If it does, then proceed slowly, allowing yourself to increasingly accept his offers right at the edge of your comfort zone. (Don’t, for example, let him sweep you off to Monte Carlo next week. But maybe accept an IPod Nano, which costs a hell of a lot less than a night at Benu.) If you know in your heart, however, that this won’t proceed beyond dating, then you’re right to hold back on accepting anything more than dinner, and you probably want to have that conversation with him sooner rather than later. Money is not just paper. It symbolizes energy and control, among other things, and it has the powerful capacity to make our lives much easier. But if you’re going to be with someone for the long run, then you have to deal with energy, control, and power in some form or another—one of you will inevitably be better looking, or more social, or funnier or smarter than the other. In this light, money is just one more form of energy a couple must negotiate, share, and use wisely.

“He” is Chris Bull, author of seven books, editorial director of Queerty.com and cofounder of GayCities.com.

“She” is Robin Rinaldi, 7x7’s former executive editor, currently at work on a memoir titled The Wild Oats Project.