The 39 Steps To Being 40: Challenge Number Six – Drink Cocktails In a Glamorous Dress and Non-Clumpy Shoes

I can’t do dressing up. It’s not that I don’t want to, it’s just that I seldom get an opportunity to do it. And I don’t really know how.

I’ve never had a job that required me to look smart. (Apart from a Christmas job in a gift shop when I was 18, when I got told off by the manager for wearing pantaloons.) I worked in subtitling for nine years in London, which is very much a casual clothing environment. Any client contact was usually done over the phone. As in “Dude, where’s the tape for the programme you’re planning on broadcasting in 20 minutes’ time that we need to subtitle?” or “Hello, you need to put in warnings for strong language and sexual content for Late-Night Countdown” or “Hi, yeah, we’ve decided to edit out three minutes in the middle of this DVD extra that you’re delivering 38 language streams for tomorrow. Will that affect the subtitles at all?” As clients plainly had no regard for our sanity, they probably had little interest in what we looked like either. And living in London, if we went out for drinks or dinner after work, we just went straight from the office, as it was always too far to head home to change first.

Then I worked for three years in a baby language lab at the University of York. No point in skirts here either – I spent half the time crawling round the floor playing with stacking cups and mopping up dribble.

And now, as a full-time mother, when I’m still crawling round the floor playing with stacking cups and mopping up dribble, my appearance has definitely ended up taking a back seat. Permanent bags under the eyes and hair in dire need of cutting are the norm. And frankly you should just be grateful that I’ve even remembered to put clothes on, so please don’t complain about the fact that they are unironed and covered in dodgy stains. None of my clothes fit me any more as my torso is a completely different shape post-childbirth, but I can’t afford to replace my wardrobe as I’m not earning any money, and anyway, if I did, everything would just end up smeared with Petits Filous.

I can’t walk in heels, and am crap at doing make-up. It doesn’t help that I have a predisposition to knee dislocations. But how do women learn to do these things? Do they get lessons somewhere that I somehow missed when I was growing up? I guess my mother never wore make-up or heels either (despite being only 5’2” tall). And I started my teenage years in the ‘80s, so that was not the best influence on the make-up front – blue eye shadow, bad blusher, hair gel. My first boyfriends seriously disapproved of women with painted faces, and being young and foolish, I let them influence me.

So my friend Beth from Book Club set me the challenge of drinking cocktails in a glamorous dress, à la Carrie Bradshaw in Sex And The City. I added the non-clumpy shoes part, since I live in trainers. It’s a shame that this had to be a challenge rather than a normal thing to do. Nights out are a very rare commodity indeed these days. I’m always exhausted, and we hardly ever get a baby-sitting opportunity.

I do love cocktails. The best cocktail nights I’ve known were my hen night in Covent Garden (though this was understandably marred by the fact that my mum was diagnosed with cancer three days before it) and one during a trip to New York in 2002, where our friend Jessamine took us to some underground bar in the Lower East Side that I’d never be able to find again in a million years, and we ran up such a huge bar bill that we just had to hand over a credit card, shame-faced, at the end of the night. But I wasn’t wearing a glamorous dress for either of those. I’m no Sarah Jessica Parker – or any of the other members of the Sex And The City quartet. In fact, I was the one usually asking the embarrassing spelling questions whenever I had to subtitle it for Channel 4.

I did wear a fairly nice white dress a fortnight after my hen do, however. And I got a fake tan, a pedicure and manicure and various bits of me tanned, waxed and plucked for the occasion. And I paid someone to do my make-up for me. But I very determinedly wore flat shoes. (No falling flat on my face halfway down the aisle for me!)

Beth also decided to help me complete this challenge, even though she is pregnant so unable to drink any cocktails herself, and arranged a night out for us. But I had nothing to wear! I had no shoes that weren’t trainers! I’ve spent the last few months comfort-eating cake! Oh, what the flip. So we had a little clothes-swapping soiree at mine to get us in the mood. No, that sounds dodgy. I invited everyone over to mine and asked them bring their smart dresses that we could exchange for other smart dresses so that we all had something new to wear. Except I was far too fat to fit into anything anyone brought. But we had fun. I scoured the York charity shops for glamorous dresses, but without success. (I’d never realised just quite how many charity shops there are on Goodramgate.) Then a passing glance into TKMaxxxxx or whatever it’s called on Coney Street caught sight of exactly the sort of dress I had in mind at a justifiable price. So I bought it. And then I remembered I did have a pair of slightly glitzy shoes that I’d once worn as a bridesmaid. I managed to remember to shave my armpits and paint my toenails. There wasn’t time to diet. I was set to go.

We (those of us who made it, and hadn’t ended up ill, stuck in Manchester or giving birth) started the evening in 1331 on Swinegate, where Beth had booked us a table. But it was the epitome of why York on a Saturday night is a bad thing. The stag do. We hadn’t even sat down before a group of men dressed as cowboys and reeking of booze leered over and began fondling us with a giant donkey. I just feel way too old to humour this kind of thing, or even find it remotely humorous. We told them to sod off. They wouldn’t. Eventually, just as we neared the chucking water at them phase, they moved on somewhere else, though not before they’d loudly dismissed us a “bunch of lesbians” because we wouldn’t respond to their advances. Mm.

By this point the music in the bar was so loud that we were growing hoarse trying to have a conversation above it (I know, I’m sounding even older now) so we moved on to the Biltmore round the corner, which was a much more glamorous dress and cocktails sort of place (though bizarrely, it has excellent baby-changing facilities, I discovered). I removed my frumpy sandals, got my glitzy shoes out of my handbag and put them on. (You didn’t think I was going to attempt to walk anywhere in them, did you?) We had a lovely time.

I drank three cocktails in the course of the evening, a Woo Woo, a Rococo Fizz, and a Godfrey. We left for home at twenty past ten. Very tame, you might think. But I knew what was coming. True to form, Charlotte was up at six the next morning. This is the way of the world at the moment. Nights out always come with a price. Hangovers are no longer an option. It’s nearly two years since I last had a lie-in.