Reader has a flirtatious relationship with co-worker, wants to ask him out

I have started thinking about my co-worker, “Oliver,” as more than a friend. We have had a very flirtatious relationship filled with banter, but have never followed through on it.

Oliver mentioned going to a bar after work in passing once, and I never followed up on this offer. Could I ask him out since I flubbed our first chance? My company has no specific policy prohibiting employees from dating.

You can definitely invite him out after work. You can even tell him that you want to take him up on his invitation from some time ago.

Ask him if he would still like to go out. Keep your date to yourselves, though. Even though your company has no stated policy about employees dating, it is wise to keep your personal business to yourselves. You have no idea what may come of this budding friendship.

If Oliver agrees to go out with you, take your time. Get to know each other, and if something comes of your friendship, you should decide together when to share the news with co-workers.

I have been receiving dinner invitations for much, much later than I would expect as someone nearly 30 years old. The people extending the invitations are nice. A couple of them are potential dates, but I just don’t want to do it.

How late is too late to be asked to dinner? I have been finding myself turning down invitations for 9 p.m. plans with no excuse other than “that’s simply too late.” I want to have a social life, but everything I have read about eating late at night says this is a bad idea. What can I do?

People eat dinner at all different times, even though, as you pointed out, it is healthier for people to eat before 7 so that they have fully digested their food before they go to sleep. Going out to dinner at 9 p.m. is very common, believe it or not. Because so many people work long hours, the dinner hour has extended this far. If you ever do go, you will see that restaurants are typically packed at 9.

If you do want to get together with the people who are extending these invitations, you can do one of several things. You could occasionally go to a late-evening dinner and be selective with your food choices. Eat light in an effort to stick to your style of eating. You can ask the person if it is possible to schedule the dinner earlier. You can say you have an early morning and don’t want to be out too late. Finally, you can come up with other activities that you can do with the people in question. Get creative with your outing ideas so that you get to see other people without compromising your eating habits.