Boomerangst: Turning Dilemmas Into Discoveries – When It’s Time to Start Dating Again

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Finding love later in life. Here, tips for when you’re ready to start dating again

Q. I’m a professional woman in my early 50s, and a single mom whose only child is about to leave home for university. My sister thinks the time has come for me to get out and meet a man for companionship, if nothing else, and she’s got a friend in mind. He’s a systems analyst who’s divorced with two adult children. She thinks we have a lot in common. I’m willing to meet him for lunch, but I’m not optimistic. I guess I’m wondering how to approach it all and if there are particular subjects we could discuss to quickly get a handle on where we’re both coming from.

Julie, Toronto


A. Before you start thinking about topics of conversation you need to ask yourself if you’re actually ready to meet someone. That’s the first step. “It’s wonderful to have friends and family who are looking out for you and encouraging you – and I do believe that everything we want in life is on the other side of fear – but you need to have desire if the dating process is going to work.”

Those wise words come from Gloria MacDonald, founder of the Toronto-based professional match making service Perfect Partners. “The right person at the wrong time is the wrong person,” she says.

“I encourage people to visualize themselves with this wonderful partner – in whatever their idea is of an ideal relationship. When you think about that does it make your heart sing and make your heart feel open or does your heart close? If it makes your heart sing then maybe it’s time to go for it – although you’ll have to step outside of your comfort zone.”

So if you do decide to go for it and go on that date?

“Just think of it as an opportunity to have fun and enjoy lunch with another interesting human being,” suggests Gloria. “Don’t put all kinds of pressure on the situation and wonder if he’s going to be the right one. Women in particular tend to put a lot more pressure on the situation and for the man to be Prince Charming.”

And don’t worry if you’re nervous. Everyone is. “No one is 100 per cent themselves on that first date – even if you’ve been dating for years. To the extent that you can,” she advises, “get out of yourself and really focus on making the other person feel comfortable and good about themselves and be genuinely and sincerely interested in them. Forget about being interesting yourself. That’s where we create rapport.”

Other advice she offers for a first date: never talk about your ex or your dating experiences thus far, and understand that you rarely find your true love on a first date. Gloria says a major U.S. research study shows that over 50 per cent of women did not even like the man they ended up marrying when they went on that first date.

“Our success rate would go through the roof if we could force adults to go out with each other three times,” she says.


Send Diane a brief description of your dilemma, along with your first name and where you live, to [email protected]

A professional journalist for more than 25 years, Diane Sewell has written for some of the top newspapers and magazines in Canada and is a baby boomer herself. Her new blog “Boomerangst: Turning Dilemmas into Discoveries” is interactive with readers and focuses on life issues – like aging, dating, second marriages, sex, death, family and fashion. Diane will use her expertise to find the right expert to help solve your predicament, unearthing kernels of truth and quickly getting to the heart of the issue.