Be brave, take a risk and rise to the occasion
Q: I’m a man in my early 60s, long divorced. I haven’t had a serious relationship for many years, but I’ve Ask Ellie 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?
A: It’s pretty simple — 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 particular day, it’s not a complete 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, whether she’s interested in a relationship, etc.
If she is seeing someone, 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 and maybe you will be rewarded.