My Top Five Worst Dates

For Valentine's Day!

Worst dates ever, in reverse order.

1. The one that was the first ever. I was 13 years old, meeting a boy I’d had a slow dance with at the school disco. The rule was: whoever you had the slow dance with – the last dance of the night – was the one you were going to go on a date with. It was a musical chairs kind of situation. We arranged a double date at the cinema in Bromley on a Saturday afternoon. So many good films came out that year: White Mischief, Hellraiser (which my Dad worked on and I was so freaked out by the set alone that I refused to see the film), Withnail and I, A Month in the Country, The Last Emperor. We won’t have seen any of those, we probably saw Three Men and A Baby.

I remember my Dad drove me there and me feeling embarrassed that he knew what I was doing. I can’t remember the friend who came with me, or what I wore (which is weird because I can remember what I wore to my first school disco: dark green cheetah print trousers with elastic stirrups that looped under my feet and an acrylic black knitted jumper. The best disco outfit I possessed that year was a sailor’s top with a navy and white striped rara skirt, from Mark One, the poor man’s Miss Selfridge).

No, what I remember is that I realised instantly both that I didn’t fancy him and he had really bad acne. I hadn’t noticed his skin in the half-light of the mobile DJ’s flashing traffic lights and smoke machine. (Why, in the 1980s, did we want to dance in a recreation of a busy box junction?) You don’t see this kind of acne anymore, thanks to modern medicine, but I’m talking craters and pus volcanos. He wrote me my first ever love letter after that cinema trip but I was shallow and mean, and I did not write back.

2. The one where I stood someone up. I felt really, really bad about this, I promise. I was working in Prime Time Videos in the King’s Road. I was 19 years old, and I was, honestly, having the time of my life. I loved working there. Paula Yates came in once, with her unruly children, and always owed tons of money on late fines. Kylie Minogue came in and was so tiny you couldn’t see her on the other side of the video racks. There was a sweet guy with long curly hair who used to come in quite regularly, sometimes with a friend of his, and it was his friend who eventually told me that Sweet Guy had a crush on me and would I go out for a date with him? I didn’t fancy him, but he was sweet, and the fact that he had a crush on me was flattering, and what was so hard about a couple of hours in a pub chatting? I said yes and the date was set.

Come the day and that afternoon some other guy came around to my flat. I did fancy this one. I’d met him at RAW, a cool nightclub on Tottenham Court Road. He was an actor, starring in an ad for Domino’s Pizza. Big time stuff. He was a bit short but he drove a cool car. He came to my flat by surprise (out of work actor) and we had a couple of, um, entertaining hours. And then I said I had to go out, to a date. And he wouldn’t let me. And I didn’t exactly insist. No mobile phones then – it’s 1993 – so the Sweet Guy sat in the pub, slowly nursing a pint, wondering why I hadn’t turned up. He didn’t come back to the video shop for a month, and when he did, he asked why I stood him up, saying that he hadn’t minded, and I made some pathetic bleat about something having come up. I still feel guilty about it.

3. The One Where Karma Got Me Back. Twice. I met a guy on a photoshoot (I was being photographed for a book), and he said he’d take me out, and my uncle looked him up in Debrett’s and he was Rather Grand and everyone was quite excited about it, until it became apparent that he wasn’t coming around to collect me for the date, after all. And there was another guy that I’d had a fun weekend with, who said he’d meet me outside Sloane Square tube station but he never turned up either. I think I even had a brick mobile phone by this point so there was no question of him not letting me know that he was late, or waiting by a different tube station (or even just the wrong exit, that kind of thing used to happen then, you know – I’m forever haunted by the Victorian bride waiting at the wrong St Mary’s and believing herself jilted). I wasn’t really that upset, I kind of felt I deserved it.

4. The One Where I Learned My Lesson. I can’t remember much about this particular date other than it was when I was at university, so in Edinburgh. I think the guy was in the year above, and he took me out for supper somewhere. The main point was that I thought it had gone OK but he never called me again for a follow up date. All my friends said: ‘What a bastard,’ and ‘his loss.’ But when I told my aunt, she said: ‘Clearly you need to look at your dating technique.’

Ha. But I don’t think she was wrong and it was a good lesson in having a friend who will tell you the brutal truth. (A few years later, I split up with a guy after we’d tried dating for about six weeks, we both wanted Something Serious but realised it wasn’t going to be with each other, so agreed to have a final date where we would tell each other what the other needed to do in order to improve their chances with other people. I know, right? He told me I didn’t suffer fools and that it could be a bit terrifying. And that could have been super useful, except that I couldn’t change it about myself.)

5. The Weird One With Two Dealbreakers. OK, so this guy I met at a friend’s wedding, circa 2003. A bit short, but a few men were then, because I was nearly six foot in my Early Noughties platform heels. We flirted at the reception, and I was very pleased with myself for resisting any snoggage. At this point, I wanted to find The One, and this meant sticking to The Rules (these had been published: no kissing on the first date, no being available the Saturday after Tuesday, no splitting the bill.) I didn’t realise then that there’s an Early Marriage stage, where some of your friends settle down quickly. There’s a panic but if this is you now, aged 25 years old or thereabouts, don’t worry – it doesn’t signal that everyone is going to be doing this. There will follow about a decade of no weddings at all, until it all starts up again.

Post-wedding, he calls, and says he’s going to take me to an exhibition, and we’re to meet by Trafalgar Square fountain at 6pm. I think this sounds pretty cool and put together my Art Gallery outfit. Kitten heels, a short skirt, some sort of cod-Chanel jacket probably. Straightened, highly highlighted hair. We meet, it’s daylight because it’s the summer, and this does nothing for his height but he seems OK. I’m on a date and this is a good thing. We go down into the bit by the fountains and I see a small crowd there, where all the people are wearing paper boiler suits with hoods. Yup. We’re not going to an exhibition – we are the exhibition.

Hot, right?

For the next hour, I wear a white paper boiler suit, with a hood pulled up, elastic cutting into my cheeks, my kitten heels clattering, carrying a small black umbrella (it’s not raining). It’s every bit as flattering as you might imagine. We march as a group around Trafalgar Square for about forty minutes and finish up on the lions for a photograph. Someone wants this moment kept for posterity but it’s not me. I’m sitting high up, feeling as hideous as it’s possible to feel, when I hear someone calling my name. Oh yes, as laws dictate, it’s an old school friend I haven’t seen for years, waving and calling my name and asking what on earth is going on. I’m bright red and waving back, and I haven’t got a fucking clue is the answer.

When we’ve handed back our boiler suits, I climb on the back of his moped (no, they are never sexy, unless it’s 1963 and you’re an Italian film star in Rome) and we go to a restaurant off the Charing Cross Road. All goes well – a large glass of white wine, a plate of carbonara – until he asks the waitress for her phone number when he pays the bill.

You read that right.

I’m sitting right there.

Somehow, I don’t leave, but get on the back of his moped – WTAF? – and he drives me back to my flat. There, in the street, I permit a snog. Perhaps I’m trying to redeem the evening. But it’s not long before I realise, it’s unredeemable. How do I know for sure? Because before I’ve even put my key in the lock, he’s puttered off, putt-putt on his silly moped, into the sunset, never to be seen again.

Enjoy this, did you? Did you laugh heartily at my humiliation? Then click a heart for me, would you? And tell me your worst dates ever….

Love,

Jess x