Dear Harlan: My mom wants to fix me up with someone she works with. He’s a cute guy who is in his early 20s. He is from another city and doesn’t know a lot of people here. I’m hesitant to go out with him because of his relationship with my mom. I don’t want to mess up their working relationship if this doesn’t work out. My mom can also be too involved. Do you think it’s a bad idea to get set up?
— Set Up
Dear Set Up: One date isn’t a big deal. Go out with this guy before diving deep into what will happen if you break off the engagement a week before the wedding. One of the biggest mistakes single people make is overthinking a first date. First, see if there is a connection. If you want to spend more time with him, ask your mom how this could possibly impact her work relationship with him. Ask what would happen if you broke up or he broke up with you. Go through some situations and see how she responds. Also, ask her how she would handle discussing the relationship with him at work. You can also ask this guy how dating him would impact his work relationship with your mom. Only have these conversations after you see if this is a relationship you want to pursue. They might surprise you and tell you what happens outside the office is not something discussed in the office. But first, have a date. You might realize there’s nothing to talk about.