CitySwoon Blog

Face to Face. Real People. Real life.

Founder Story: Secrets of a Professional Matchmaker co-founder and matchmaker Louise O’Connor combined her web coding skills with her knack for matching up single friends on amazing real dates, to create a dating site with a difference.

Louise O’Connor loves to get singles together. It all started when she set up two of her university friends, and they ended up married. A while later, Louise was living in London, when she went to a hen’s weekend and met five single women.  “I was working as an IT programmer in investment banking; writing code to price bonds, options and futures for the trading floor. I was the only girl on the team,” says the avid matchmaker. “My single colleagues were always reading books on how to meet women… they didn’t know where to start! So I decided to do five separate set-ups with my new single girlfriends” she explains.

Louise played matchmaker, as well as date coordinator, researching the thriving London single scene and the best places to go. She sent her matches to five of the top hot spots. “One was a blind date in a blind restaurant,” says Louise, “the waiters are blind and they guide you blindfolded to your table – so my friends didn’t actually see each other until the end of the date!”

Louise’s singles all had a ball, and she did too – “I was hooked!” she says.

Connecting the dots…

Back in Sydney, Louise had a brainwave. “I decided to combine my matchmaking and programming skills and create a brand new kind of dating site.” was born – matching compatible singles and getting them to meet on real dates in the hot spots of Sydney. With over 400 face-to-face dates set-up in just three months, Louise and Cityswoon are on a roll, which is great news for single Sydneysiders!

Single? Here’s where to start!

Just flicking through profiles on a dating site won’t tell you if there’s chemistry, says Louise; “Maybe they tick all the boxes – they’re smart, the right height, have a great photo. But you never really know until they’re standing right in front of you, if they’re going to make you swoon.”

That’s why Cityswoon is all about meeting face to face on group dates and one-on-one dates. “We want you to meet the person, not the profile,” Louise explains.

She wants members to find that dizzy, butterflies-in-the-stomach feeling. But chemistry is not everything, says Louise; “You can swoon for the wrong person – if you have the feeling they’re not trustworthy, or you’re not on the same page personality-wise, you need to walk away before you get attached.”

So what makes a great match? 

“You’re more likely to work out if you really click,” says the matchmaker.

“It helps if you are aged within six years of each other… obviously relationships do work outside of that, but statistically it’s true” says Louise.

“Similar backgrounds or values are also important, as is a similar level of optimism and positivity.”

“Compatible goals for the future help as well,” says Louise. “If you have different feelings about wanting kids you’re going to run into trouble down the track,” she adds.

Hot Date Tips

“Nerves and shyness can get the better of anyone,” says Louise. “Ironically, the best thing to increase your confidence is to step outside your comfort zone and do something new!”

Meeting new people on a first date can be particularly daunting, but Louise advises faking it till you make it. “Your date has no idea how you’re feeling on the inside, so just look them in the eye when you approach them, smile and introduce yourself confidently. Fake it long enough, and you confidence becomes real!”

“For most people, those initial nerves settle down pretty fast,” says Louise. And if you can’t hide the butterflies, don’t worry – this can be a big compliment to your date!

“The other person will also be nervous,” Louise points out, “so just focus on helping them feel more relaxed. Ask them easy questions when they first arrive, like ‘have you been here before?’, ‘was your trip here ok?’ and so on.”

Practice makes perfect, says Louise. “The most important thing, when you’re looking for that special someone, is just to keep getting out there. If you go on a CitySwoon date every day this week, those initial flutters will all but disappear by date five!”

If you’re shy, you start with a CitySwoon group date, Louise suggests, “you can bring a friend and hang out with a bunch of fun people. You might meet someone you really click with. And even if you only make friends, your new friends may have a single friend who does make you swoon!”

Starting the New Year single? Make History!

Being single in Sydney this summer is a great opportunity, says Louise. “You can be a part of history and set a brand new Guinness World Record at Cityswoon’s ‘World’s Biggest Blind Date’. We are so excited about this once-in-a-lifetime event – and my biggest set-up yet!”

On February 21st 2014, over 700 single Sydneysiders will gather to party in a stunning venue at the iconic Sydney Opera House, overlooking the harbour and the bridge. I’m going to match everyone up on a blind date, and there’ll be all kinds of great activities and chances to meet new friends and maybe even that special someone who makes you swoon!”