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?

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