Ask Amy: What did my friend mean by this comment about my husband’s death?

Dear Amy: I am a widow, and after my husband’s death I became friendly with a man who knew my late husband.

“Frank” has helped me out with some business matters, and I’ve grown to really like him.

After talking by phone, texting and going out for dinner (where we both seemed to have a great time), out of a clear blue sky Frank said, “It’s going on three years since your husband died.”

What does this mean?

Is he saying it’s time to move ahead in this relationship, or is he maybe saying that it’s time to stop seeing each other?

We are both adults and single.

I’d appreciate your directions.

– Wondering Widow

Dear Wondering: Here are my directions: Turn to your right. Find your phone. Use it to ask Frank to do something non-business-related.

I suggest that you float the idea of grabbing a coffee and going for a walk in the park, because that’s what worked for me the last time I asked a man out.

This may seem like a terrifying thing to do, but if you’re ready to get back out there, a little bravery is called for. I hope you’ll follow up.

Dear Amy: Our 30-year-old son, “Thomas,” has a great job, is well-adjusted, and has many friends.

He is outgoing and socializes with groups of friends, some of whom are married.

He is not dating anyone and hasn’t “dated” (that we know of) since high school (i.e., going to proms, dances, etc.).

Thomas and I have a close relationship and talk about most any topic, except his lack of dating or of having a special someone in his life.

I want to ask him why he doesn’t date, but I don’t want to put him on the spot in case that is not something he wants to talk about with his mother.

My husband is not a very good communicator and I think if he asked our son this question, it would be a very awkward conversation for both of them.

My husband and I joke to Thomas that we need some grandchildren soon (he is our only child) and we all laugh it off without any real responses.

If Thomas is happy not being in a relationship or dating, that is fine, as he seems very happy with everything else in life.

It seems odd to me that he and I can talk about most other things, and yet I never bring this topic up to him. We did superficially discuss dating when he was in high school, but nothing since.

Should I bring this topic up to him (and how should I phrase it), or should I let our overall good relationship continue the way it is?

– Curious Mother

Dear Curious: You say that if your son is happy and well-adjusted without having a “special someone” in his life, you’d be fine with that.

According to you, he is happy and well-adjusted.

And now it is time for you to be fine with that.

Bugging your son to provide you with grandchildren is obnoxious. It’s also not funny, even though he graciously laughs it off.

The possibilities here are:

• He is gay and choosing to keep this from you.

• He is dating lots of people (women, men, or both), but not telling you about it because he fears you’ll start advocating for marriage and grandchildren.

• He’s asexual and/or not at all interested in partnering up, and is moving through this stage of his life happily on his own.

• Or he’s out there looking, but he doesn’t want to discuss it with his parents because he is a grown man and has lots of other people to discuss his romantic life with.

I think the way to open up this topic (and also lay it to rest) would be for you to say to him, “I’m sorry for those times we’ve bugged you about having grandchildren. I hope that hasn’t made you too uncomfortable. I also hope that if you ever have a ‘special someone’ in your life, you’ll let us know.”

Dear Amy: I see it is getting close to wedding season. Every year I look forward to all of the questions about bridesmaids, showers, in-laws, etc., in your column. Many of them seem so silly!

I’m relieved that I don’t have to go through this again (I hope!).

– A Fan

Dear Fan: Oh yes. Fielding these annual questions is like standing in front of a confetti bomb.

You can email Amy Dickinson at askamy@amydickinson.com or send a letter to Ask Amy, P.O. Box 194, Freeville, NY 13068. You can also follow her on Twitter @askingamy or Facebook.