Charly Lester

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dating blogger, Charly who knows a thing or two about the dreaded dating having launched the first ever national dating industry awards. She’s now global Head of Dating at Time Out. Yes that is TOTALY a thing…We caught some words below (your sex life can thank us later).

Where in London do you live and what do you love about that area?

I live in Clapham Junction, though my neighbours keep telling me off for calling it that! Apparently it’s officially Battersea (or at least that’s what the bins say). I love it – everything is on my doorstep, from incredible brunch options, to cocktail bars and high street shops. And yet it’s still possible to disappear down a side street and feel like you’re in a leafy residential suburb.

Tell us what you do for a living and how that came about?

I’m Global Head of Dating for Time Out, which I like to think is one of the coolest job titles going! Time Out actually created the role for me at the start of this year, and I now split my time between the London and New York offices. I’m a dating blogger at heart – I began blogging about dating in 2013, on my blog 30 Dates. Three months later the blog was picked up by the Guardian, who ended up asking me to edit all their online dating content. Then last summer I set up the UK Dating Awards in response to emails I was receiving from blog readers who wanted to know which dating sites and services they could trust.

The crazy part, which I still can’t quite get my head around, is that this time last year, I was still working full time in banking. I started my blog after a guy messed me around online, and I wrote an off-the-cuff Facebook status suggesting I might try to go on 30 blind dates, in the 3 months running up to my 30th birthday, as a way to remind myself how much fun dating can be. Less than two years later, and I have a completely different career, and what I consider to be my dream job, all because of my response to being rejected by a guy!

Charly Dating Awards

In terms of dating, what do you think people overlook, or need to be aware of, try harder at?

I think it can be really easy to get set in your ways, when it comes to dating. I have lots of friends who go to the same pub, and order the same drink, and the only variable is the person they’re sitting opposite! But the exciting thing about living in London is that there are so many cool things to do. None of us have as much spare time as we’d like, and dating can feel like a waste of your free time, if you don’t meet someone you want to see again. I always try to encourage people to think out of the box, and go to events or venues they wanted to try anyway. That way, you can get a true feel of the other person, and it is a lot less like a job interview. And then even if you don’t fancy them, you didn’t waste your evening!

Where do you think would be an ideal place for first time dates?

I always recommend doing some form of activity – because it’s a lot less daunting to chat while you’re side by side, instead of sitting across a table from one another. I’ve had great first dates at London Zoo, taking a jet boat down the Thames, and playing Urban Golf beneath High Street Ken station. If you do want to do something more traditional, try to find a bar or restaurant with a bit of personality. Mr Fogg’s is a really different bar, and I love the cloak and dagger feel of Evans & Peel Detective Agency. The Shed is one of my favourite restaurants in London, and I also had a great first date in the dark at Dans Le Noir. Be adventurous and have fun!


What would be your perfect date in London?

Haha, that’s quite a tough one, as I’ve probably been on at least 100 first dates for my blog, and now that I’m no longer single, I drag my boyfriend out on ‘date nights’ at least twice a week! One of the problems with being a ‘dating expert’ is that I’m very rarely surprised any more, so my perfect date would be one which I haven’t done any planning for! I love pop-up stuff, and not knowing what’s coming next. Last month we went to the Gingerline, which was great, because the food was incredible, and the whole event was shrouded in so much mystery. But then last night I went to Duck and Waffle for the first time, and staring out of the window had one of those ‘God I love London’ moments. I think as long as I get that excited rush at some point during the date, I know it’s a good one.