Today, I have a date with destiny.

Okay, that’s not strictly true. I just said that for dramatic effect. Today I have a date with a personal shopper, which is much more terrifying. I am not good with clothes. I’m actually terrible with clothes. I dress half my age because it’s easy to pull on a baggy jumper and jeans and be done with it. I don’t know how to wear skirts or scarves. Anything that requires actual thinking (“Where does this arm go? How does this belt close?”) doesn’t belong in my wardrobe. Neither does anything that requires ironing, anything that has to be dry cleaned, or anything with prints. I don’t wear prints. Unless I one day find myself in a scenario in which I have to camouflage myself against brightly-patterned wallpaper in order to secure state secrets, I highly doubt that will ever change.

So I am meeting a personal shopper. She sounds elegant. Her name is Olga. She calls me ‘My darling’ on the phone, and the last time we spoke she ended the call with a “See you on Friday, my darling. I love you!” which was a nice touch.

Although I’m pretty sure that was accidental.

In so far as going in prepared, I don’t have a plan in place for this meeting. The aim is to get some clothes that look more I-am-successfully-adulting, and less teenage-boy-with-moobs. Since I clearly cannot be trusted to pick out these sort of outfits for myself, I will be deferring all authority to Olga. The only thing I have asked of her is that she bring me no ruffles. NO CAPES! And no ruffles.

After making the initial appointment, I had to answer a few questions online. The e-mail link called them ‘a few simple questions.’ I should have suspected something, but instead I blithely clicked the link and started to scroll down the page. The questions started off fairly straightforward – they asked for my height and my weight, my favourite colours, my favourite brands and my size in different items of clothing. I answered them all with ease, feeling pretty accomplished. YES! I thought. I KNOW THIS! LOOK AT ME GO!

Of course, no sooner had I clicked onto the next page than I realised the form wouldn’t be the cakewalk that the first page of questions had led me to believe.

“Who is your style icon?”

Grumpy Cat.

“What body shape are you? Oval? Round? Rectangle? Square? Hourglass?”

Fearing the trapdoor to hell that I imagine instantly opens beneath the chair of the egotist that clicks ‘hourglass,’ I went with ‘rectangle.’ I am not rectangular in any sense of the word but neither am I square, oval or round. I am an hourglass that has been slowly compressed from above until it bulges out the sides. I am a stumpy hourglass. I am the hourglass that they sell with 70% marked off because it’s misshapen and inelegant.

Unfortunately, that wasn’t an option.

“What is your colour direction?”

Here they offered a long list of options, none of which made any sense. I mean, what does that even mean? When you google it, the search results are all clustered around some sort of hair dye, which wasn’t of any use. There were no ‘I don’t know’ or ‘Help!’ options so I closed my eyes and clicked at random. Very helpful I’m sure. Sorry Olga.

I clicked the ‘Finish’ button with no small measure of relief.

So today is the day. Today Olga and I come face to face. Mano a mano. I’ll be wearing my trusty Adidas superstars with faded black jeans that have seen better days, and an oversized grey knitted jumper. I want her to get a real, honest look at what she’s working with here. I don’t want to dress up and have her lulled into a false sense of security. If we’re to give this thing the chance it deserves, she’s going to need to truly grasp that I know absolutely nothing about clothes. Our working baseline needs to be down around ‘colourblind clothes-bank raider’. Just about half a step above ‘toddler with velcro light-up trainers’ but a step below ‘child who knows how to wear a skirt.’ I’m actually feeling quite nervous about it.

Olga, bless her heart, has her work cut out for her.*

Please wish me sartorial success, I suspect I might need it!

*UPDATE: You can find the full report here for anybody curious about how the process works and whether or not I bought velcro light-up shoes.