I’m a man in my early-60s, long divorced. I haven’t had a serious relationship for many years, but I’ve had close female friendships from my former workplace.

I’m now dealing with health issues – some more serious than others, but under control.

I met someone I’d like to date, but I’ve lost self-confidence in that area. I don’t even know where to begin.

I see this woman weekly, as she’s a librarian at the library near where I live. We always have a very pleasant conversation.

She’s warm and chatty and has a nice sense of humour which is important to me. She’s also attractive but not showy, and I like that.

She’s younger than me, by about ten years, though I haven’t asked directly.

I’d like to ask her out but I’m terrified she’ll invent some excuse and I’ll be too embarrassed to even see her at the library again.

Should I just acknowledge that I’m past dating and give up?

Too Late to Date?

No risk, no gain.

You’re racing ahead of yourself and imagining the worst.

You’ve had friendships with women before this which suited your mutual interests.

Now you share interest with this woman in books and discussing them.

When it seems appropriate – soon - casually suggest getting a coffee together (not a drink) when she finishes work so you can carry on the discussion further.

Even if she can’t make it that day, it’s not a rejection.

Keep chatting. You need to start on the basis of friendship, because there’s lots you don’t know about her.

You’ll both become relaxed enough to gradually fill in some blanks, e.g. whether she’s involved with someone.

If yes, making a new friend of her is not a defeat. It can lead to more friends and even to dating someone new.

Don’t let fear of rejection hold you back.

From divorce, and health issues, you already learned that life is about meeting challenges, not hiding from them.

Take the risk.

Recently we attended a two-event wedding.

My wife (the groom’s Godmother) and I were invited to the Saturday evening wedding/reception and a Sunday brunch for out-of-town guests.

As the whole weekend went over budget, the brunch was downsized the night before to breakfast for the couple and five relatives.

When winding down, I thanked the groom for breakfast for which I’d assumed he was still paying. He looked stunned but quickly recovered.

I joked about how I get a lot of meals paid for in this manner but quickly offered to split the bill, which we did, $150 each.

My wife thinks I committed a very insensitive faux pas with my premature thanks. I think I did the right thing since it never dawned on me that the couple would ask their guests to chip in for this long-planned event. Who’s right?

Eggs Over Visa

You’ve naturally led me to a Dr. Phil quote: “Do you want to be right, or happy?”

Your sign-off shows you’re a man with humour and you joked with the groom. It’s highly unlikely that he was offended by your suggestion, and you recovered graciously by paying half the bill.

Weddings are expensive, and this couple initially over-reached.

However, their minds are now focused on the honeymoon, and married life… not on what you said.

Your wife, as groom’s Godmother, was naturally sensitive about his feelings. Tell her she has a good point and you respect her for making it. Then give her a hug.

FEEDBACK Regarding the woman having difficulty handling her “out of control” stepson, 11, during summer-long visits (July 16):

Reader – “These three words of hers stand out: "He doesn’t care.”

“He obviously does care and is showing it through his actions.

“This stepmother’s looking for blame (Ellie: her husband’s ex enforces no rules on her three sons).

“His stepmom needs to help him. How is isolating him from play while watching his two older brothers have fun, constructive?

“I was a youth-care worker in an adolescent ward at a psychiatric hospital for 15 years.

“This couple need to get direction, now. He's an adolescent boy, not a monster.”

Ellie – I appreciate your own background in working with troubled children.

I agree that both parents (and hopefully, eventually the boy’s mother too,) get professional guidance themselves.

They need to understand, get diagnoses for the boy, and deal with his potential psychological and possible physical issues which are affecting his behaviour.