He’s happy? Let him be

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

He’s outgoing and goes out 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., proms, dances, etc.).

Thomas and I have a close relationship and talk about most topics, 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 awkward for both of them.

My husband and I joke to him that we need some grandchildren soon (he is our only child). We all laugh it off without a real response.

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 up this topic to him.

Should I bring this 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 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. Possibilities here are: He is gay and choosing to keep this from you.

He is dating lots of people but not telling you about it because he fears you’ll start advocating for marriage and grandchildren.

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

Or he’s out there looking but doesn’t want to discuss it with his parents.

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 am a widow and after my husband’s death I became friendly with a man who knew him. “Frank” has helped me with some business matters, and I’ve grown to really like him.

After talking by phone, texting and going out for dinner (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.”

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

I’d appreciate your directions.

Wondering Widow

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

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 a terrifying thing to do, but if you’re ready to get back out there, a little bravery is called for.