Photo: Flickr/Creative Commons, fly.

“My gal pals assured me that first dates were just like a riding a bike, that instinct would kick in and I’d instantly remember how to go about it,” says Jennifer Blackwell, as she recounted her first post-divorce date. “My 24-year marriage ended two years earlier and I knew I wanted to explore dating again. I wanted – felt I deserved – someone special in my life. At the age of 52, I had a fairly good handle on what kind of man I was looking for. But I’d forgotten how to navigate the initial step – the proverbial first date.”

Blackwell, with the encouragement of friends, registered on a dating site, met a man and, after a series of emails, agreed to meet for dinner. “My girlfriends encouraged me in every possible way. They did everything – except counsel me on the mechanics of the evening itself. I hadn’t been on a first date in 26 years.”

Online dating is a popular way to meet prospective partners for Boomers. Photo: Flickr/Creative Commons, R. Reeves.

Lessons learned from dating disasters

Three hours before the scheduled rendezvous, Blackwell’s date emailed her to say he had a “better” restaurant in mind. Blackwell, slightly hesitant but wanting to demonstrate she could go with the flow, showed up at his recommended venue: “It was a noisy pub in Mississauga and he was there with a dozen of his mates for a darts tournament. It wasn’t the one-on-one scenario I was expecting.”

At one point, she suggested they take their drinks to a table in the corner for some one-on-one. His response? ‘Whah? Don’t be anti-social. Stick around and we’ll go back to my place later.’ Blackwell didn’t have the dating savvy to leave then and there. She stuck around for three hours before cabbing it home. Obviously, the three-email exchange wasn’t enough to give her a sense of what kind of guy he was or what he was truly looking for.

Did the experience discourage Blackwell from dating again? “Not at all!,” she says. “The ‘Ian Hiccup,’ as I call it, only made me more determined to do things my way and come up with a strategy to navigate first dates.”

Been there, done that: Advice from dating trenches

Lisa is a 60-year-old Toronto marketing executive. She met her partner, Yves, on a blind date when she was 53 and he was 54. Both had been single for about 10 years when they met. “I had a decade of first-time-dates under my belt by the time we met so I followed ‘my rules’ and it all worked out.”

Not surprisingly, Lisa frequently shares her hard-earned lessons with friends and acquaintances. “One of my rules is to always talk on the phone first to get some idea of personality and temperament, sense of humour and if you have enough in common to be curious about getting to know the person,” she said.

“I had a decade of first-time-dates under my belt by the time we met so I followed ‘my rules’ and it all worked out.”

Her other essential rules include: be on time, pay attention to your date (not your phone), ask as many things as you tell about yourself. She also doesn’t expect her date to pay. “I also don’t expect him to flirt with the server – that happened – and I don’t want to hear he’s still living with his ex-wife while they sort out property and separation details.”

And yes, that also happened. “Being over 50 means you have learned to cultivate patience and you won’t compromise,” she says. “You know who you are.”

6 tips for successful, drama-free dating

While everyone’s dating journey will differ, relationship experts offer some basic ground rules to help navigate that all-important first date.

  1. Manage expectations

“Dating is a journey, not a race,” says Jacquie Brownridge, professional matchmaker and managing director of It’s Just Lunch, a matchmaking service with branches in Toronto, Vancouver and Victoria. “It helps to set a safe, fun, initial expectation. Start by looking at the date as a first introduction to an interesting person who happens to be single. Just take it one step at a time. Don’t let your imagination get ahead of you.”

  1. Where to meet and what to do  

“The ‘space’ for a first date is important,” insists Brownridge. “Find a place that is social, not too private, as that could be uncomfortable, and not busy as that could make it hard to connect. A safe, public restaurant or cafe for lunch is ideal, as it has the added benefit of seeing how the other person interacts with people like the hostess and waiters. Researchers have found that sharing a meal together enables better connections than a walk, a movie, or just a coffee.”

Experts are split on the effectiveness of a coffee date. Yay or nay? Photo: Flickr/Creative Commons, Nick Webb.

But Shanny Tebb, of the Toronto-based matchmaking company Shanny in the City, dismisses coffee dates. “A first date in a coffee shop seems cheap, rushed and often lacks ambience. Coffee dates often turn into interviews rather than a fun date.”

  1. What to talk about

“Treat the first-date conversation like a friendly exchange, not an interview,” says Brownridge. “Bring a few conversation starters that are open ended, fun and non-judgmental. People are most natural when they talk from the heart about things they enjoy. It’s important that both of you have a chance to do so.”

And be mindful of dating no-no’s, adds Tebb: “Avoid talking about your ex, divorce, failed marriage, finance problems, health issues, etc. Keep the date upbeat and positive.”

  1. Communicating before the first date

Do you text, email or talk on the phone? Some prefer the sound of a voice, others learn more from lengthy emails. “The world has changed and how we communicate has changed,” says Tebb, “If your date texts you, don’t take it as a bad thing. Simply communicate how you wish to communicate. If you prefer a phone call, simply schedule in a time to chat with your date.”

  1. Dealing with nerves

“If you are over 50, you may be asking yourself: ‘Why am I in this uncomfortable position of dating at this stage?’” says Brownridge. “It’s important to remember that you are not alone. About half of Canadians experience divorce, while others have lost a partner. Your date could be feeling the same.”

First date jitters? Take a bath or meditate. Photo: Flickr/Creative Commons, Risto Kuulasmaa.

Meanwhile, Tebb has practical tips to reduce nervousness: “Avoid the last-minute stress of picking out clothes and figuring out how to find the rendezvous restaurant. Do all of that in advance. Also, yoga, a hot bath or a walk in the park can also ensure you arrive feeling relaxed and calm.”

  1. Personal safety – practical and pertinent

“I feel it’s important to meet in a public place, and to have a reservation. Make sure a friend knows where you are going and with whom. And avoid drinking too much,” advises Brownridge.

Happy dating!