Interview with Charly Lester Speaker & CEO of the Dating Awards

Few people know the dating industry as well as Charly Lester. Her position as CEO of the Dating Awards means if there’s something going on in the industry – she knows about it!

How would you sum up your role? A difficult question for someone who wears so many hats!

Haha, that’s quite a tough one to answer. Ok, so I started life in the world of dating as a blogger, writing ’30 Dates’. I then moved to journalism for the Guardian and Time Out, and now work as a freelance journalist for various sites and publications, including eHarmony, AVIS and While I was working as the Global Head of Dating at Time Out, I set up the UK Dating Awards, and am now CEO and Founder of The Dating Awards – which I run in London, Amsterdam and New York. When I’m not working on the Awards, I do freelance consultancy and PR for a number of sites, apps and dating companies. I also run regular Guardian Masterclasses in blogging.

What path did you take to what you’re doing now?

It’s certainly been an interesting route, and completely unplanned. I began the blog on a whim – by writing an off the cuff status on Facebook, and setting myself a challenge to go on 30 Blind Dates before my 30th birthday. The rest has really happened quite organically, with a lot of the opportunities coming to me off the back of other stuff I was doing within the industry.


Any challenges you’ve overcome on the way?

Setting up the first UK Awards was particularly scary. I was setting myself up for a huge fall – financially and personally – if it failed. I had to prove myself in an industry where virtually no one knew me, and get people to trust that I was in it for the right reasons, but thankfully I soon realised I was the most powerful selling point of my brand. If I could get face to face with people they saw my enthusiasm and began to understand my vision for the Awards. I have to admit, I’ve definitely been underestimated on more than one occasion because I’m a ‘girl’.

What’s your favourite part of the job?

Every day is different! And every month there is something new and exciting to get my teeth stuck into. One minute I’ll be filming a documentary, or writing an article, the next I’m attending a cool event or flying to the other side of the world. I love the fact I’ve managed to create my own job, and I quite enjoy the thrill/fear of knowing I have to earn enough each month to pay my rent!

Biggest work achievement to date?

I was an expert advisor to Lord Sugar in the final of last year’s season of The Apprentice. We filmed over 6 hours at City Hall, and I had to share my thoughts on Vana’s dating app with both Lord Sugar and Claude.

Any funny/crazy/stupid things you’ve seen/done along the way?

Oh god – I’ve been to some awful dating events. I’ve sat silently gazing into strangers’ eyes at Ssh Dating. I’ve sniffer t-shirts at Pheromone Dating, and I’ve played British Bulldog in Clapham Common with Give a Damn Dating.

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What do you enjoy most about being a guest speaker at the Matchmaker Academy bootcamps?

I love speaking at the Matchmaker Academy. It’s such a great atmosphere for learning, and I’m very fortunate to get to speak with some of my closest friends in the industry. It’s always really interesting hearing their answers to certain questions, because 9 times out of 10 we all would have given the exact same answer. One of the most valuable things I’ve learned about working in the dating industry is to surround yourself with people who inspire you, and the other speakers at the Academy are people who inspire me and make me want to drive my own business forward.

Any advice for people looking to get into matchmaking or the the dating industry?

Meet as many people as you can who work in the industry, and work out the ones you think you would work well. Success in this industry requires networking – it’s very hard to succeed alone without referrals and partnerships, so get chatting to other people in the industry and work out what you can do together.

If you have a question for Charly she’d love to hear from you, tweet her @30dates