Ellie Tesher is on vacation. The column below is an archived favourite, personally selected by Ellie

Best of Series Part 3: March 7, 2016

I’m an unattached male, 61, although friends say I look 50. I have post-graduate degrees, no dependents. My wife’s long gone.

When I was in a community theatre production last year, I took an immediate interest in a female volunteer.

I didn’t mention my attraction then, but later contacted her.

She responded through Facebook. We’ve stayed in touch. She’s 40ish, has one teenage child, and I don’t detect any ongoing relationships.

Recently, we discovered we’re working together again and are getting along very well.

I want to “make a move,” but typically, my fear of rejection is present. I don’t share my affections casually.

Also, I’m not focused upon physical intimacy.

Am I being a hopeful/hopeless romantic, or a chicken?! Is the age difference irreconcilable? Should I wait until we’re not working together in a production?

Timing or Timidity

Enjoy whatever friendship develops while working together but don’t talk about your attraction during this time.

(There’s enough intensity in theatre work without complicating it, and the wait won’t be that long).

When it’s over, suggest doing something together such as seeing some other show, listening to music, etc.

If she accepts, you’ll be relating in a new setting, as individuals rather than cast members.

That’s when you have to draw on the confidence that you bring to a stage, and state your interest in dating her.

The age difference isn’t what matters. It’s whether she has a similar attraction to you, and whether she’s interested in having a romantic relationship.

You’ll find out most comfortably by taking it slow getting to know her beyond this limited exposure surrounded by other cast members, then finding an appropriate time to speak up.

My mom and step-dad aren't officially together anymore, she hangs out with this other guy.

He's pretty cool but I'm not looking forward to having ANOTHER stepdad. She’s now saying that everything's perfect because of this guy.

I don't want HIM to ruin my family, future and life!!

But everyone in the family likes him. Worse, things aren't going too well for me in school.

I never really knew my father, and met my step-dad when I was two-years-old. I’d gotten so attached to him, and she's probably going to take that away from me.

I’ve talked to my mom but she just says I'm being silly.

Not Another Step-Dad

Tell your mom that you’re not a “silly” child but you are a scared daughter.

That’s something she can understand and help you get over.

But first you must resist accusing her of ruining your life, because that only pushes you both apart.

She’s apparently chosen a man who’s decent and even “cool” in your eyes, so he’s not going to ruin your life either.

You’ll even understand your mom better if you talk to him, and see what it is she likes so much.

Since your step-dad and you had a good relationship, you’ll likely be able to stay connected unless your mother has very good reasons otherwise. (If so, ask her to please explain to you what she can).

School is a major part of your life, too – your center of friendships, adult guidance, the path to your future.

Talk to your mom about having difficulties there that may be due to the changes at home.

You’d benefit from seeing the guidance counselor or an outside counselor to help you get back to focusing on school and making whatever adjustments you need at home.

FEEDBACK Regarding the husband bested by his wife at arm-wrestling (February 11):

Reader – “Men needing to be stronger than women is a stereotype too often perpetuated.

“One shouldn’t hide or sugar-coat their abilities, especially those they’ve worked for, to make someone else feel better about themselves.

“For too long girls have been taught that they don't need to be physically strong because “that's the men's job.” This message is especially harmful for teens such as myself.

“The woman didn’t initiate the situation. If her husband can't be proud of his wife, it’s an issue with him not her.

“For their union to overcome this issue, it’s the responsibility of both to explore the source of the rift in their relationship.”

Ellie – Your strong, confident opinion’s accurate and admirable. I agree that they can encourage his fitness together, since she asked for advice how to ease his embarrassment.

As I wrote, natural competition between them is fine.