Q. I fancy my friend's dad. He's single and a good laugh, and I swear he flirts with me. I'm tempted to make a move, but would it ruin the relationship with my friend?

A. While inter-generational relationships do work, when it involves your mates' parents it comes with baggage. Acting impulsively could have serious consequences for your friendship. Would you want your friend as a step-daughter? Don't rush into anything, just focus on having fun with your friend. This might be an occasion where you ought to wait for him to make the first move, then decide, but discuss the possibility with your friend, and make sure she's OK with it, before you rush in.