(MONEY Magazine) - My friend Scott drives a BMW 760Li with a refrigerator in the back seat (MSRP: $118,900). He has a Hummer too. He sold the Lamborghini, and now he's thinking yacht.

Scott is 32. He runs his own credit-card processing business in Boston, which evidently is doing quite well. He's the kind of guy who likes to try the hot restaurant and maybe rent a limo to get there, just for kicks. Once in a while, I feel awkward about how much more money he makes than I do--like the first time he drove over in the Hummer and I, who at the time drove a pickup truck I later sold for $100, wondered if we could still relate.

But Scott didn't grow up rich--far from it--so he makes sure not to act like a show-off or make his friends feel like freeloaders. "When a person orders an expensive bottle of wine, you can't get up and walk away just because you can't afford it," he says. "So now I don't order the expensive wine. I don't want to do that to anyone."

Wealth disparity can drive a wedge between even the closest friends. This is increasingly a fact of life in today's winner-take-all economy, where some skills are in fevered demand and others are, well, not. And it can make a friendly lunch feel weird.

Currently, the average salary for a first-year associate at a big law firm is $125,000, while an advertising account executive makes around $48,500. "The gap between college graduates going into lucrative positions and those going into more normal positions is exploding," says former Clinton labor secretary Robert Reich. "We've not seen a time in living memory when so many young people made so much money, and some peers are wondering what they have in common anymore."

Is there a solution? I asked all kinds of people--even Donald Trump. (After all, when is he not the richest guy at the table?) Turns out he's sensitive to the issue, pointing out, "No one wants to feel guilty for being rich or poor." I learned what in a way I already knew: If two friends are close, money probably won't tear them apart, but both need to step carefully to avoid feelings of guilt, inadequacy or, worst of all, resentment.

BE HONEST "I went to college with kids whose parents were loaded," says Scott. "I tried to keep up, but after I got into debt, I'd just say, 'Sorry, I can't swing it.'"

GIVE A LITTLE If you can't afford to split the check, say so up front, offering instead to cover the wine or the tip.

CONTRIBUTE IN OTHER WAYS If Mr. Fast Track invites you somewhere and he's paying, ask how you can help. Make reservations? Pick up the tickets?

SOMETIMES, SUGGEST BURGERS Don't always choose four-dollar-sign eateries. "That's like making your friend say, 'Sorry, I'm incompetent,'" says Daniel Kegan, a psychologist who studies money issues. Tasting the foie gras ice cream at some hot spot isn't worth making your pal feel like a loser. Send a message that quality time is paramount; pick a cheap place.

TREAT--WITH PURPOSE Treating too much can make friends feel inferior, so give an excuse. "I'll say it's a thank-you for a favor, or a late birthday gift," Scott says. "That way it's not a handout."

TREAT--JUST FOR FUN Occasionally, it's okay to pick up a dinner for the gang as a show of friendship. Trump's technique: "Say there's a new place you want to check out, and that it's taken care of. Treat it lightly, like it's no big deal. One of the perks of wealth is the ability to be generous." (By the way, Scott, if you're reading this: I think the Donald is absolutely right here.)

To help kick off the Rules of the Game column, we'd like to help you turn the tables on your richer pals. Tell us, in 200 words or less, why you deserve to treat your friends to a night on the town. If you win, you'll get dinner for four, plus a limo for the evening--on us.

E-mail your entry to contest@moneymail.com or mail it to Contest, MONEY magazine, Room 17-102, 1271 Avenue of the Americas, New York, N.Y. 10020.

Deadline: March 15, 2006.