My worst first dates

And why I lied about my age - upwards

Hello, and thank you for reading The Honesty Box. If you’re in the UK, I hope you’ve enjoyed the Queen’s Platinum Jubilee celebrations and are ready for a little light reading about my dating life.

But before I tell you about my worst first dates, I’m going to do two things. The first is to ask a favour.

If you like what I write here, I would REALLY love it if you would forward this to a friend (or two?!), and perhaps ask them to subscribe if they enjoy it (it’s free). The Honesty Box is almost a year old and I’m on a mission to get it out into the world a little more. You can forward this email on, or send a WhatsApp link, share the homepage on Instagram, Facebook or whatever your preferred social media is!

In return, if you or your friends have questions about life as a 40-something, about not having kids and how that can be OK, or how to change your mindset, or anything they wanted to know about being a freelance journalist or how to manage self-employment, I’m very happy to answer in the comments below. Think of it as an ‘ask Lucy anything’ setup. Many thanks in advance!

The second is to tell you that The Honesty Box now has a shiny new logo, designed by my art director friend Chris Eade, which you can see at the top of the page. He’s managed to make it look like a little honesty box speech bubble, complete with coin/thought slot. Now I feel like a real professional newsletter-writer, ready to share content with the world! Thanks so much to Chris, who you can find on Instagram here.

So now on to today’s topic: two of my worst first dates (and the one where I lied about my age).

I’ve been single on and off for a while, and in my 30s (I’m now 44, woo!) I tried pretty much all the dating apps - as well as asking friends to set me up – in pursuit of finding The Husband I Could Procreate With And Then Live Happily Ever After With – The End. A couple of years ago, I let go of this obsession, and can now look back fondly at my escapades in the pursuit of love, plus mention a few things I learned.

Here goes:

Sweet Nothings Man

If I have one rule for dating, it’s never to have dinner the first time you meet, especially if the person is a stranger you met on a dating app. Dinners are for intimate catch-ups with a friend, tipsy fun in a group or for more romantic encounters with a longer-term lover.

First date dinners can A) take up a whole evening, B) be expensive, C) be fairly interview-like and D) involve alcohol, which I tend to avoid early on in dating, and for me this combination doesn’t make for a light-hearted fun time. For me, the perfect first date is a couple of hours long and might involve a walk in the park, a gallery or brunch.

Sometimes we can self-sabotage because we’re fearful of the things that can go wrong in relationships

Anyway, when a guy I was due to meet suggested dinner, I asked if he would mind if we did an early evening drink instead, which he didn’t seem all that pleased about, but we met in Soho where we sat at high stools at a bar.

We had chatted on the phone beforehand and I went with an open mind. His chat was all about other dates, and soon he told me about a woman who had whispered something in his ear soon after they met. A slight invasion of personal space, I thought, but not a dump-able offence – until he did the same thing to me. “Shall I tell you what she whispered?” he asked. “OK,” I said, thinking I ought to play nice. He leant over, getting a bit too close. “I have herpes,” he whispered heavily and hotly in my ear. Sweet nothings it wasn’t, and I left soon after.

People talk about red flags in dating, and I think there were a few when I spoke to that guy on the phone before meeting. It’s sometimes hard to know when to listen to the voice inside that says ‘I’m not sure,’ and turn a date down, while at other times it’s easy for that voice to put you off someone for no reason. Sometimes we can self-sabotage because we’re fearful of the things that can go wrong in relationships, but you never know until you try.

Dog Man

I was set up with Dog Man through a friend of a friend and we met at one of the gates to Regent’s Park in London to walk his Labrador towards a pub in the chic Primrose Hill area. The park provided plenty of pretty flowerbeds to admire and people to watch - so far, so pleasant. But when we got to the pub, said dog decided to start sniffing around under our table, including up my skirt, which I found funny (his owner didn’t).

What I think I could have enjoyed more is the journey, rather than being so concerned with finding a husband

Sense of humour failure in Dog Man aside, his pet then started exploring the pub garden’s flowerpots, which were planted with colourful pansies. I was relieved to no longer have the dog’s attention, but then it started EATING the flowers, which I objected to, as I know how much cultivation pots of flowers can take. My date did nothing about it, and after a pizza (yes, we had dinner), we said goodbye, and I never saw the dog or the date again. The dog was definitely wayyyyy more interested in me than his owner.

I’m not sure if I learned anything useful from this date, but perhaps I could have asked Dog Man’s friend more questions about him before we met. I tended to get so excited about the fact that an actual human (rather than a swiping app) has set me up with an actual man, who is available and willing to date, that I fail to ask what their redeeming qualities are. I doubt I would have discovered his tendency to let dogs eat plants, but still.

Why I lied about my age - upwards

Lying in general is a poor quality to have, but I do think that having to specify an age-range on a dating app can tap into prejudices, and when I turned 40, I felt that might be a turn-off for a man in his late 30s, so was tempted to shave off a couple of years. I now realise that wanting to hide my age was a sign of insecurity in myself, and freely talk about my age (have I told you I’m 44?).

The one time I did lie was because I experimented with a different approach. A few years ago, London was dominated by posters advertising the dating app Lumen, designed for ‘the over-50s,’ and I decided to give it a whirl – the only problem being I was only 41 at the time. But never mind – I uploaded my photos, wrote a snappy description of myself and what I was looking for, and set my birth year to 1967, making me 51.

Eventually, I matched with Ted, a 50-something outdoors-type who lived in east London, and we arranged to meet for brunch. The night before, I decided to come clean and explain that I was looking for a more mature man and told him my real age. I said I’d understand if he preferred not to meet because I’d lied about being 51, but he was happy to go ahead.

Ted was kind and nice looking with a great smile, and we got on really well for a few months. Ultimately, nothing came of it because he was still sore after a separation and wanted to date someone who definitely didn’t want kids (he had two, didn’t want more, and I was still in the market for some) and we stopped seeing each other. Do I regret pretending I was older than I am? No, because we had a great time together.

So, there you have it. Tales of my adventures in dating, most of which I tried to learn from. Looking back, what I think I could have enjoyed more is the journey, rather than being so concerned with finding a husband. It is a cliché, but letting go of the outcome and accepting myself has been so liberating. I’m sure I’ll write about this more.

Something I like

Sunshine and dancing

A song about sunshine has been going around in my head for a few weeks, after the DJ Annie Mac played it at Before Midnight, her new club night for people who like their sleep. I finally worked out what it was this week: You Brought The Sunshine, by The Clark Sisters. It sounds like a classic piece of 1960s’ soul, but it’s actually a gospel tune from 1981 and it’s super uplifting.

Thanks to Albert Dera and Unsplash for the image that goes with this post on the archive page.