Things You Only Know If You’ve Been On 100 First Dates

Charly Lester, 35, challenged herself to go on 30 blind dates before turning 30. Then things snowballed...

100 first dates

by Charly Lester - as told to Emma Elms |

My dating adventures began when I was ghosted by a man I nicknamed ‘Henley Boy’. I was 29 and had been wandering around grinning like a Cheshire cat after several successful dates with him, only to end up miserable when he cut contact. It was frustrating that a man I barely knew could have such an effect on me.

I only had three months left of my twenties and decided I wasn’t going to spend them moping around. Instead, I wrote a Facebook post announcing: ‘I’m setting myself the challenge of going on 30 blind dates before my 30th.’ I’d never been on a blind date before and am notoriously picky, but asked my friends to set me up with some ‘nice, normal’ guys, ‘preferably over 25 to avoid the inevitable cougar jokes’. Within a couple of hours, I had 50 comments and multiple shares. My friends loved the idea, offering me their brothers, neighbours and friends. Several suggested I start a blog, and my first entry was read by more than 2,000 people in one night. With my ego bruised by Henley Boy, my aim was to put the fun back into dating. I wasn’t looking for The One.

I set myself ground rules, like sticking each date out for at least two hours and not using any real names on the blog. I had to go on three dates a week to fit them all in before my 30th. I was open from the start that I’d be writing about it, so most had already read my blog before they met me. It was fascinating to view myself through my friends’ eyes. One guy was so badly matched to me that I texted my friend afterwards, saying, ‘I’m confused. Why did you think we’d have anything in common?!’ I’m sporty and only a moderate drinker, but one evening this guy turned up completely drunk. He was outrageously rude, loudly insulting everyone on the Tube, while I cringed – worried that bystanders might think I was his girlfriend. It’s the only time I’ve ever told someone off on a date.

I’ll never forget the one who turned up in a crocodile outfit so I’d know who he was, and another who held up a sign reading, ‘I’m your blind date.’ For date 30, I hiked up to the Hollywood sign in LA with an American guy – I’d flown out there to see a friend for my birthday. It ended up being the best summer of my life. Women from all over the world began emailing me for dating advice or telling me about their own ‘Henley Boy’. After completing the challenge, I was having so much fun that I decided to carry on.

I went on 100 first dates over two years. In the process, I landed a job as a dating expert for The Guardian, then became global head of dating for Time Out before launching my own international dating awards and app. I was having a great time – and enough success that I was able to quit my main job as a financial contractor. And as for romance? I didn’t sleep with any of my 30 dates – and there was only one of the 100 where it was love at first sight (‘Mr Second Chance’). He was in the army, living at Sandhurst, and we ended up meeting on New Year’s Day. I’d been on so many dates by then that I’d become quite complacent about it. I rocked up to Waterloo station in jeans, a jumper, glasses and a bobble hat. Suddenly, my dream man appeared – tall, muscular, blonde, wearing chinos and a tweed jacket.

We had an amazing time jet-boating down the Thames, and he even drove me home to Reading afterwards. The date lasted for 10 hours, and he’s the only one of my 100 dates who I think I could have married. We dated for six weeks but, sadly, I realised it was impossible for me to get serious about someone who was in his situation, because he had no control over his life. Still, even if I didn’t find a relationship, I don’t regret how many dates I’ve been on. I’ve learned that no matter how confident someone is, everyone gets nervous before dates. (If you’re shy, a sporting activity is ideal, as the distraction fills any awkward silences.) And the conversations you have on first dates with strangers are unlike any other – you often end up talking about things you wouldn’t normally, like the fact I went to Venezuela for a month when I was 17 or lost both my parents to cancer at 19.

Yes, I did have one nasty experience, where a guy set up a page slating me with a link to my blog, saying, ‘Look at her – she thinks she’s happy being single, but she’s fat and ugly.’ Six months earlier, that would have upset me – but by that point my confidence had grown so much through dating that it didn’t bother me. Since ending my blog, I’ve had two long-term relationships, but now I’m happily single again. I would like to marry and have children one day, but I love the freedom I have – the fact that I could jump on a flight tomorrow if I wanted to. And I find it funny how people feel it’s acceptable to ask a woman in her thirties, ‘Why are you still single?’ but no one ever asks, ‘Why did you marry him?’ Being single is exciting. You never know what’s around the corner, or who you might meet next. Believe me, I should know..

Charly used her expertise to set up Lumen, a dating app for over-50s – the fastest growing dating app in the UK;

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