Charly Lester

Charly Lester. Not so stupid cupid.

Models from the Harrow School of Gymnastics

Rishiel Gudka:

Daniel Ward:

And Parkour Generations

Chris Keighley:


Hair and make up: Aliyah Haji and Mackenzie Malcolm.


Charly Lester is a surprising young woman.


She is the UK’s best known dating industry expert, the former Head of Global Dating at Time Out, the founder of the Dating Awards in London, Amsterdam and New York and one-time adviser to Sir Alan Sugar when his Apprentices were tasked with launching their own dating apps.


Her achievements in this arena would have put Jane Austen’s Emma Dashwood into a tailspin of 18th century astonishment and unalloyed admiration.


It would be easy to dismiss Twickenham-based Charly as a one trick pony; someone who hit a nerve with the dating public and turned it into a business. That would be to under-estimate Charly and the serious trend analysis and precision she brings to the world of match-making.


Charlotte-Cristina Lester, to give use her full name, has a lot to offer.

In a world where the London School of Economics has just announced that having a partner is the top pre-requisite for happiness, Charly’s ability to assess the cold, hard facts of the warm and wonderful world of dating is both unrivalled and, more importantly, very illuminating.


An indication of her intelligence comes from her academic background. She is a Cambridge graduate in Law - she received a 2:1 – and has a Masters in Broadcast Journalism. She has produced her own documentaries in Asia. She has written for the New York Times and consulted for the Guardian newspaper. Yet the clue as to why she puts such great store on our closest relationships lies in her own personal life.


Charly lost her parents within 10 months of each other when she was just 19. Her father died first when she was travelling on a Gap Year before moving to Cambridge and her mother died when she was in the first term of her degree at St Catherine’s College.


It is the love story of her parents’ which informs and emphasises the importance she puts on finding the right partner.


“My parents were soulmates. They were each other’s everything. My Dad was English, and my Mum was Romanian. He was backpacking through Europe, and ended up in Romania by accident. His train broke down in the middle of the night, and he had to find accommodation in a town with no hotels. He met a woman on the road who owned a student boarding house, and when he got to the boarding house the residents were all celebrating my Mum’s 23rd birthday. My Dad continued on his travels, but returned to Romania for Mum. Throughout much of their engagement and the first year of their marriage, they were separated because of the difficulty involved with getting visas in the seventies, and so they communicated in a series of love letters, all written in French, which was their common language at the time.”


“When Dad died suddenly of a brain tumour, my Mum completely lost the will to live. He had been her rock,” said Charly.


“I guess that is why having the right relationship is important to me. I grew up seeing just how good it can be when it works.”


Of course, Charly gets as anxious as anyone else about finding the right personal relationship. That is how her whole foray into the entrepreneurial side of romance began.


“I was 29, and had had a bad experience with online dating. Rather than let it affect me, I wrote a jokey Facebook status suggesting to my friends that I would go on 30 blind dates in the three months left until my 30th birthday. My friends loved the idea, and suggested I turn it into a blog.”


The very first blog post was read by 2,000 people on the first night, and within weeks ‘30 Dates’ became the most successful dating blog in the UK.


Charly had some interesting evenings that have taken her far away from her natural habitat on our stretch of the Thames. She went to Dans Le Noir, the dining in the dark restaurant, for a real blind date. Then she went to a Circus pop-up evening where she sat since most of us would settle for the local pub or a trip to the cinema.


Not long after, she went to a Guardian Soulmates evening at Vinopolis on the South Bank and wrote a review for her blog. The newspaper loved it so much they hired her as a consultant. Soon she was editing their dating blog and by April 2014 had set up the UK’s first Dating Industry Awards. Clearly on a roll, she then became Time Out’s Global Head of Dating before setting up the European Dating Awards in Amsterdam in 2016. Last September she took the Awards to New York.


It is all long way from the White Swan in Twickenham where we met just after one of her hot yoga sessions on Richmond Hill.


These days, her latest venture is SPEX, an online dating site for people who wear glasses.

It is a natural fit. Charly wears glasses most of the time. She always looks rather studious but scrubs up amazingly well; she just thought the sex need to go back into spectacles and she was the girl to do it. She could be right. She takes her specs off for yoga, triathlon training and other forms of exertion but they are nearly always poised on her very attractive, inquiring face.


It is no surprise to me that she was a top student at Kendrick Grammar School, near Reading who achieved the series of top grades at GCSE and A Level needed for admission to Cambridge. On leaving university she went into banking but felt it did not suit her skill set. She was right.


Above all else, Charly loves entrepreneurial ventures backed up by solid trend analysis and serious research. She doesn’t lose sight of romance but she does think the path to truelove requires a strong, resilient and practical approach to dating.


That is why she will be writing our regular dating column for RiverTribers in search of a mate. She will cover the facts you need to know, the hard truths and the soft options, the best way to close the deal and why sometimes you should walk away.


In short, there will be invaluable advice from someone with a business-like approach but with their heart in the right place.

©RiverTribe Magazine 2017