Question: I recently heard about a conference that I’d like to attend — my boss agreed and approved my registration, even though the fee was around $1,000.

The conference takes place in a city that’s either a short flight or a long drive from where I live; I was planning to fly. Well, a colleague of mine mentioned to our boss that she would like to go, too. Our boss said he’d only pay for her to attend if we drive together. He doesn’t want to pay for two round-trip plane tickets.

I could go alone and fly, but she’d be shut out. Also, I can’t stand this particular colleague. The idea of spending 10-plus hours on a road trip with her makes my skin crawl. Should I quickly book flights and then say sorry, I already made reservations last week?

Answer: I think it’s crummy of your boss to put you in this position! He must either be completely unaware that there’s trouble between you and your co-worker, or he enjoys putting other people in complicated ethical situations.

I would not book flights now and pretend you booked them last week. You’ll have to submit a receipt as part of your expense report, I assume, and your boss will be able to see the booking date. I think your best option is to suck it up.

Get some audiobooks if you’re worried about talking with your colleague for that long. And look at it this way: At worst, you’ll come away with some good stories about how awful she is. At best, you might get to know her a bit better and find out she’s not so bad.

Q: Are you supposed to leave a tip on the table or in the little folder they bring the bill in? My brother-in-law makes a big deal of always leaving it on the table, kind of spread out so the server (and everyone else) can see how much he’s tipping.

A: Either way is fine. But even though I think it’s great your brother-in-law is a generous tipper (or at least I assume he is!), putting on a show about how generous you are is tacky.