Meghan Markle and Prince Harry have a matchmaker to thank for their love


Happily ever afters don't always happen by themselves. Sometimes they need a little nudge.

As you're likely well aware, Prince Harry and Meghan Markle are tying the proverbial knot in Windsor this weekend. Something you may not know is that the royal couple were matchmade by mutual pal, Violet von Westenholz.

"It was definitely a set-up," says Markle. "It was a blind date. I didn't know much about him and so the only thing I had asked her when she said she wanted to set us up was, I had one question, I said 'Was he nice?'"

("Nice", by the way, is our #1 ask from our straight female clients. Not rich. Not tall. Not a legitimate prince. Good on Meghan Markle for getting her priorities straight!)

Matchmaking your single friends is one of the kindest things you can do for them. But it can also be one of the biggest disasters. Good thing Violet von Westenholz has a knack for it! 

Last year, I wrote a column in The Toronto Star about how to matchmake your single friends. In honour of the upcoming royal wedding, we're reprinting it below in order to help any budding Violet von Westernholzeseseses out there. Maybe you'll be responsible for the next fairy tale wedding!


So you think you can be a matchmaker?

It’s thoughtful and considerate to engineer romantic happiness for your single friends. But if your formula for setting people up is no more sophisticated than “They’re both single and seem to smell OK,” you need to fine-tune your strategy.

Here is the honest truth about set-ups: most people are bad at it. This is partly because most people are not very good romantic fits for each other.

Human beings: complex.

Finding love: hard.

Having been on the receiving end of some nightmarish set-ups and hearing horror stories from friends and clients, I know for a fact that setting up the singles in your life is something of an art. It requires intuition, logic, faith, finesse and a whole lot of luck.

Here are some things every budding yenta should keep in mind before accidentally subjecting their long-suffering friends and relatives to yet another disastrous blind date:

Do their lifestyles align?

If one of your single friends is a steak-loving workaholic corporate lawyer, and their would-be match is a raw vegan visual artist/freelance photographer, exactly what will they talk about on their first date? How about for the rest of their lives? This is a fun pairing for a sitcom but a seriously bad idea for a set-up.

What are their hobbies/interests/passions?

People love to talk about the things they’re most passionate about. Whether it’s the Toronto Blue Jays or health-care policy, indie music or municipal politics, the nuances of the latest HBO series or the craft cocktail menu at a trendy new local, great conversations are built upon common interests. Similarly, great relationships are built upon good conversations.

Do they have similar values?

If your friends adhere to a religious faith (or different religious faiths), consider complications that may arise with their respective families or when potentially raising children down the road. Political leanings are also important. Most people tend to be pretty open about dating those with different political viewpoints, as long as they are open-minded enough for friendly debate. That said, you probably shouldn’t match a left-wing activist with a staunch social conservative. Another solid sitcom idea, though!

What do they want down the road?

Some people want a white picket fence in the suburbs and 2.5 kids. Others want to forgo kids and real estate and spend their golden years sailing around the world. Some want to establish the first human settlement on Mars. Where do your friends see themselves in 10 or 20 or 30 years? Do they ultimately want the same things? Don’t throw them together if they don’t.

Is there the potential for physical attraction?

Looks shouldn’t matter, but they do. A lot. Ask your friend or family member what and who they find attractive (do they have a “type?”) and don’t set them up with anyone who falls too far outside of those parameters unless you feel super strongly that their personalities would really click.

Have you asked if it’s OK to set them up?

You should definitely do that. A few years back, someone introduced me to someone else completely out of the blue via Facebook message. She didn’t know me very well and hadn’t ever asked me what I was looking for in a person — or even if I was looking at all. The man was not my cup of tea and extricating myself from that situation was deeply awkward. Be sure to ask permission of both parties before setting them up. Exception: you feel like being sneaky, so you invite them both to a group gathering. This is a solid strategy for organic interaction but not necessarily welcome if it’s too obvious a move.

And now, for a story: I was very recently set up by a friend and had a lovely time. My date was smart, funny, cute, pop cultured, hosts a radio show (as I once did) and our tastes and senses of humour aligned like planets. Although it didn’t go anywhere (blame our complete lack of romantic chemistry and the fact that he lives in Vancouver), it was still a fantastic set-up and it was crystal clear that our mutual pal has a solid understanding of us both. I appreciated the care he took and the thought he put into it.

Matchmaking your friends is a good deed, indeed. Just make sure you do it well.

This article originally appeared in The Toronto Star