DEAR ABBY: I am a 40-year-old single mom who is just getting back into the dating scene after being divorced for a year and a half. There is a guy, "Hank," I'm interested in getting to know better. We both have kids who go to the same high school. We have gone to several out-of-town football games with our kids and have texted each other often.
What's bothering me is Hank has never asked me on a one-on-one date. Should I ask him, or should I wait for him to make the first move? I don't want to appear desperate, but I really would like to get closer. -- STEPPING BACK INTO THE SCENE
DEAR STEPPING BACK: I wish you had given me a little more information about Hank -- such as why he's raising his children alone and for how long, and whether he dates at all. However, I don't think it would be overly aggressive to say (casually) to him, "You know, we never get a chance to talk one-on-one, and I'd like to get to know you better. Why don't we have dinner one night?" It's not an obvious proposition, and if he's at all interested he'll agree.