Mo' Money, Mo' Problems

We asked TheStreet.com financial guru Farnoosh Torabi, author of You're So Money, how to navigate a few sticky predicaments.

Q: Can I turn down a request to sponsor my officemate's breast-cancer run-walk without sounding like Scrooge?

A: Gently decline by complimenting the cause, then explaining, "I wish I could, but I've already used up my annual charity budget. Otherwise, I'd go broke giving to every cool nonprofit." Finish the letdown by promising you'll help spread the word and that you'll consider her cause in the new year.

Q: I'm a lightweight, so I dread group outings where people inevitably order rounds of cocktails, then split the bill. How do I gracefully wiggle out of bankrolling somebody else's buzz?

A: Take control of the situation by schmoozing your server, then quietly requesting a separate check for your order. If anyone asks why you're keeping your own tab, explain that you're trying to get a better handle on your spending and need a receipt to keep track of your expenses.

Q: My boyfriend insists on footing our dinner bills — but he always stiffs the help. Should I slip them extra cash or confront my man about his tightwad tips?

A: Teach by example. Next time your guy attempts to tip with a wrinkly five-spot on a $50 dinner, insist that you'd like to leave the tip since he generously paid for the meal. As you lay down $10 (make sure he watches), respond to his raised brow by telling him you paid your way through college by busing tables and have a soft spot for the waitstaff. This way, you've started a conversation, not a confrontation.

Q: My supervisor gave me a really nice (read: expensive) birthday gift. Can I return the favor without becoming a brownnoser?

A: Heed the old cubicle adage "Never gift up" — meaning, shower gifts only on those who rank below you. However, if you and your boss are close, go with the always-appreciated gag gift — a Meat of the Month Club membership for the aging-frat-boy boss, for example. He'll walk away amused, with you to thank for it.

Q: I'm uncomfortable when coworkers talk bonuses. Is there a polite way to tell someone to butt out, or am I being too sensitive?

A: Money isn't as taboo as it once was, but you've still got every right to keep it confidential. Deflect the question by offering a cool brush-off like, "It's now bonus money for a clerk at Saks." If your friend is an earthling, she'll get the hint.

Click here for more from the MONEY CONFESSIONS PACKAGE

Real-Life Money Confessions

5 Secrets of the Highest-Paid Women

The Purse Diaries: What Women Spend