Herndon: I'm a youngish woman, 25, who has worked in a two-person division of a larger firm for nearly a year. My boss, the other half of our division, is in his late thirties. We have a very friendly and supportive work relationship, and I would consider us friends outside of work as well. My problem, if you can call it that, is that he often invites me to join him for meals during the workday. Sometimes we chat about work and other times we chat about life, but he always picks up the check. He also always does the inviting.
My question is, should I be offering to pay for some of these outings, or my portion of them? I know that he expenses some of them (but not all) to our company. At the same time, I typically bring my meals to the office to save money, so I wouldn't necessarily be looking to eat out if I wasn't invited.
On the face of it, I'd say there's nothing wrong with him taking you out to lunch. It's pretty common for senior people to take junior workers out to lunch. It's a normal part of the mentoring relationship.
However, if something else about the lunches is making you uncomfortable, it's worth a pause to look at the bigger picture. Are you worried that his interest in you might not be entirely professional, or that perhaps it might look that way to others? Is there something about the frequency of the meals, or the price of them, that just feels off? If so, address that with him. Otherwise, enjoy the lunches and the great boss!