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The Do's and Don'ts of Matchmaking

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Here's the rules for playing cupid.


Being a matchmaker is a tough job. But someone’s got to do it. We’ve all been there. We see two people who would be just right for each other and we can’t help but get things moving along.

Whether you’re bored of listening to your friend’s dating disasters or know you can set them up with someone way better, remember the urge to play matchmaker can either help or hinder your friendship.

Here’s what to do and what to avoid when you’re playing cupid:

The Do’s

First ask them if you can be their wingman

You can’t set them up with someone if they aren’t willing to meet them. Ask if you can help them look for someone first. 

Listen to what they would like in a potential partner

It’s not about you. Whatever your personal opinion is on who they should date, at the end of the day, you’re trying to find someone for them, not you! If they’re looking for someone older, interested in specific activities or someone who is different to their ex, the key is to listen. Try to tick 3 out of 4 boxes so there’s room for them to be surprised. 

Help organise their first date

Eliminate some of their anxiety by picking a date they both are comfortable going on. There’s nothing worse than a mediocre first date, and the setting plays a big part. Is going to see a movie going to reduce the time they have to talk?

Is dinner at a fancy restaurant… plain boring?

Will a high intensity activity just get their hearts racing for all the wrong reasons?

Choose the venue or activity you think they will have the most fun with and will bring out their personality.

Encourage them to date outside their type

If it’s a bad boy they always go for why not persuade them to go on a blind date with someone you think will treat them better. You should still listen to what they find attractive and try and find a happy medium. 

Give them advice only if they ask

I know it can be hard to hide your opinion when you’re trying to play matchmaker but it’s alright to let them know e.g. if their chat needs work or what outfit they should go with. You want to help build their confidence, not just state where they’re going wrong.

The Don’ts

Use this as an opportunity to have fun

If you’re serious about finding your friend someone they would be happy with, don’t treat this opportunity for your own amusement. They’ve trusted you with the task of introducing them to someone you think would be right for them. Affairs of the heart shouldn’t be treated as a joke. Save the memes for the group chat after the date.

Become the third wheel 

After the introduction, it’s important to let them get on with it. It’s okay to get a debrief from your friend after the date but orchestrating how the relationship should move forward is not your call. 

 Be over critical of anyone who might not meet your “standards”

Your friend may have a checklist of who they want, you may have a checklist of who you want and trying to find someone you’ll both be happy with, will become near on impossible. 

Tell them everything about the person you’re setting them up with

Reduce expectations and let them surprise each other. It can be so tempting for both of them to do a quick social media search on each other before the date, but sometimes going in blind can give them both an idea of who they really are in the present and not in a socially constructed profile online.  

Sign up now with your wingman by downloading the Wingman® app in the App store and Google Play store. Available in the US and UK for IOS and Android devices.

All Gifs via Giphy

Photo by Elena Koycheva on Unsplash

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