Please send your questions for publication to prudence@slate.com.

Dear Prudence,

At a recent work-related occasion for merrymaking, I found my boss and I were two of the last people present. Alcohol was freely available, and he asked me if I wouldn't have one more drink with him. I hadn't seen much of him at the party, but as we talked I realized that he was maybe not three, but at least two sheets to the wind. He was also alone and faced a 20-minute car ride home, including a stretch on the freeway. I had no access to a car at the time.

I was concerned for several reasons and ended up ruffling a feather or two. Can you recommend a tactful way to point out that a superior is, let's say, not fit to operate heavy machinery or a motor vehicle?

—Puzzled

Dear Puzz,

Prudie is dying to know how you ruffled the feathers—and whose. Did you put your well-oiled boss in a cab or conscript a co-worker to chauffeur Old Granddad? In any case, since you ask about future approaches, there really is no tactful way to tell a guy he's too drunk to drive. People who have had a snootful respond differently. One person may be amenable to the "suggestion" that he be driven home, another might become belligerent and argumentative. In either case, do your best to prevail, and it is likely that a sobered-up person will thank you in the morning. If someone is really blotto and you can get your hands on the car keys, do that. Then get him a ride home, or failing that, plunk him on the nearest sofa.

—Prudie, protectively

Dear Prudence,

I've recently had a strange development in my social life. I'm a 20-year-old college student whose roommate turned 21 not too long ago. Predictably enough, my roommate likes to go to bars. Unfortunately, he can't bring himself to go without a "wingman," and this duty almost always falls to me. Even though I look old enough to get into bars, I never drink because I'm usually the designated driver. In any case, what almost always happens is that I sit at the bar with my roomie and watch him have fun and chat with the ladies. I don't really feel comfortable in bars, but I go to keep my roommate happy (and alive). Should I suggest my roommate find another "wingman"?