How to play Cupid (without shooting yourself in the foot)

When you know two people who would be just perfect for each other, matchmaking seems like a great idea.

However, if you do set two of your friends up and it all goes horribly wrong, you could end up losing those friends or getting stuck in the middle of many future awkward situations.

Deciding to Make a Match

The first rule when trying to play cupid is to remember that just because these friends are single, it doesn’t mean that they are desperate. Ask a few basic questions about what they are looking for, and things they are attracted to. If their descriptions match with the potential mate you’ve picked out, you then need to think about whether they have anything in common besides being single and if you could actually see them together.

Paula Stephenson, a professional matchmaker based in Calgary, interviews her clients extensively before setting them up with anyone, but uses her intuition to determine matches. Gut instinct goes a long way, and if your gut is saying no, then you might want to refrain from making a match.

If you still think it’s a match worth making, you need to give a fairly accurate description of each party and be sure not to gloss over anything important in the hope that the incredible chemistry between them will make these things unimportant. Omitting details that could be unpleasant surprises or deal breakers (such as being a heavy smoker or being chronically unfit) will just lead to awkwardness later.

Engineered Situations vs Blind Dates

Once both parties have agreed to the set-up, you can either provide details and retreat, or you can keep on meddling by organizing a get together of some kind (this is especially good for shy friends.)

Stephenson found that setting couples up on blind dates worked best. “I set up a little place that serves great desserts and coffee, that’s a positive atmosphere,” she says, but adds that when she has thrown “networking stomping grounds” for singles, those events have also yielded great results.

When Lara* connected with Kate, an old friend from high-school, on Facebook, she was sure that she would be a great match for her best guy friend, Tim. “She was a bit hostile and told me how she hated everyone always trying to fix her up with the loser in their life,” says Lara. “I convinced her he wasn’t a loser and she let me get him to contact her on Facebook.”

In no time at all, Kate and Tim were messaging back and forth daily. “When they finally met at my Christmas party they were stuck to each other all night. That was almost a year ago and they are still together,” Lara says. Using a non-threatening approach like that worked well for Tim and Kate, and may be a good way to engineer a somewhat safe set-up.

If It Goes Badly

Given that there is no accounting for chemistry, there is a fair chance that your matchmaking skills may fail spectacularly and you’ll hear about it in graphic detail. You may want to issue a disclaimer before introducing people, so they know that you cannot be held to blame if things don’t work out. Stephenson makes her clients sign a stringent policy that says “As with anything with life there are no guarantees, there may be some small quirk that the one person can’t live with, and it is no reflection on the person that was matched up.”

When Carla introduced her oldest friend to an acquaintance of her husband, she thought it would be a match made in heaven. “It wasn’t,” she says, “I wish I’d never set them up.” Carla’s friend ended up marrying the guy and having a baby, but their relationship is, “seriously messed up with so much baggage,” and Carla can’t help feeling like she is to blame, especially when her friend complains about her husband to her.

Stephenson says that the biggest dangers in playing cupid are when people misrepresent themselves (such as by saying they are a ‘light drinker’ when in reality they are a bit of a lush) or haven’t dealt with their personal baggage and aren’t really ready to be dating.

“So far I have only had one couple that didn’t work out and, luckily, neither has blamed me for getting it wrong yet. Once again, it was a case of misrepresentation on what each other were truly looking for in their futures,” says Stephenson. “Honesty really is the best policy when dealing with a matchmaker.” With all this being said, it’s only fair to realize that the same rules apply when you’ve been set up with someone and that if it all goes wrong, you can’t lay the blame at the feet of the matchmaker.

If the person they set you up with isn’t right, be tactful and discreet. Point out why they weren’t quite right for you instead of slamming your pal’s taste in men/women or else, next time the opportunity arises, they’ll introduce that hottie to someone more appreciative of their efforts.

* Names changed to avoid destroying friendships!

Article courtesy of Click by Lavalife.

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