Toby Young

I – a Lesbian – Dressed Up as Toby Young to Get Into Gentlemen's Clubs

In 2000, Toby Young "dressed as a lesbian" to try to deceive women in gay bars into kissing him. Seventeen years later, can I reverse the trick?
08 January 2018, 3:01pm
All photos by Bekky Lonsdale

Last week, Toby Young – the journalist, commentator and serial editor of his own Wikipedia page – was appointed to the board of the Office for Students (OfS).

Some in the Tory party were thrilled with the appointment. According to a tweet from Boris Johnson, Toby "will bring independence, rigour and caustic wit. Ideal man for job." Universities Minister Jo (brother of Boris) Johnson, who appointed Toby (ex-employee of Boris) Young to the role, said the OfS "will rightfully put the interests of students at the heart of regulation" and work to reform Britain’s higher education sector.

Young, who has never held a teaching post, insisted that all regulators need outside influences. But is he the right sort of influence?

One week and over 50,000 of his deleted tweets (including sexist and homophobic claptrap) later, a warning came from Theresa May that "if he was to continue to talk and use this sort of language, then he will no longer be in public office". But he wasn’t just saying these things or one-fingeredly jabbing them into Twitter posts; he was making a living off them.

One article from the annals which struck as pretty tricky to reconcile with his newly appointed status as one of the 15 arbiters of student life is titled "I Was A Lesbian For A Night". In the piece, for GQ, Young dresses as a woman and tries to get into a few of New York's dyke clubs so he can "approach gorgeous young lesbians, draw them into my confidence, then make out with them on the dance floor".

Young's justification for his creepy desire to become a lesbian amounted to "two words: pillow fight". Toby Young also once closed a magazine he edited, Modern Review, after one of its female writers left her husband to shack up with another female writer. Was he not aware that lesbians do more dramatic things than have pillow fights?

Toby Young was 35 years old when he posed as a lesbian, yet he wants us to believe that it was a mistake of a long-forgotten youth; that he’s a changed man. I'm not so keen to let it go. What I want to know is: if Toby Young can dress up as a lesbian to get into a lesbian bar, can I – a lesbian – dress up as Toby Young and get into men-only private clubs?

First, I'd need to look the part. Toby Young has compared himself to William Hague, but I go for a drop of Buck Angel, a hint of Heston Blumenthal, an earnest nod to Harry Hill and a splash of a guy I went to uni with who once used a "Je Suis Clarkson" meme as his Facebook profile photo.

It’s lucky Toby does the exact same "I'm just off to All Bar One for an executive lunch, see you later, dickheads" blazer-and-jeans thing Mick Hucknall did in the early 2000s, because I dressed as Mick Hucknall last Halloween so already have all the right clothes.

I used to be what Toby Young might call a "hardcore dyke", and during that period had a crewcut – but I grew it out because, ironically, people kept confusing me for a young boy. Stifling this scarecrow’s head of tangles with a £6.99 bald cap isn’t easy.

But I get there!

As I’m dressing up as a man so easily distracted by tits that he felt compelled to tweet about the "huge knockers" on Danny Boyle’s then-14-year-old daughter, I realise I can’t afford to have my own boobs get in the way of my disguise: a sports bra under my shirt and jacket straps everything in, just in time for a make-up artist.

Unfortunately, however, VICE doesn’t have the budget GQ had in 2001 to pay professional make-up artists ahead of reporters going on ludicrous cross-dressing missions, so instead I'm forced to make use of some old watercolour sticks.

I’m now ready to charge into male spaces with the entitlement of a man who suggested to his wife, when she thought she might have miscarried, that the pregnancy might be a phantom one, and that maybe, in his words, she'd "see the funny side".

I’m prepared to hold my glasses on the tip of my nose and peer over them with all the hubris of an amateur magician. I’m all ready to live a day in the life of…The Toadmeister.

And away we go!

(I muttered something to this guy about not being in the paper for the first time in days. Understandably, he ignored me.)

First stop: lunch.

Toby likes sushi – it’s the food he chose for his lunch during the FT interview in which he announced his unsuitability as an education campaigner, uttering the words: "I think, presentationally, the powers-that-be would prefer it if I were a black working-class woman."

I soon get talking to a fellow bloke at the front desk.

"Hello, where are the nearest gents clubs?"
"The toilets are at the back"
"The nearest gentleman’s clubs?"
"Would you like to pay your bill?"

I head over to Parliament Square to search for some political inspiration.

At the altar of Sir Winston Churchill, I think of his quote, "Success is going from failure to failure with no loss of enthusiasm." I remember this because Toby Young once used it in an article – about his own career trajectory – called "Failing Upwards".

I order an Uber.

"Are you Sophie?"
"Yes, that’s right: Toby."

Before I know it, I’m at Pratt’s, a gentlemen’s club founded in 1857.

I press the "club" button and no one answers. I press the "office" button and a woman – maybe one with stonking big baps? – answers.

"Hello, I am Toby Young and I would like to come in."
"This is the office, do you mean the club?"
"Yes, I would like to come into the club."
"The club is closed, they are not in today, they are on holiday."
"Oh, but I’m Toby Young and I’d like to come in."
"I’m sorry. Maybe you can come back."

Considering this exchange takes place via a video camera, I do well to keep her on the phone. But it's not enough. I want to be part of this world. I want to be where the rich men are.

A-ha! The Gaslight of St James’ gentlemen’s club!

Alas, what a shame for self-confessed porn addict Toby Young: this "gentlemen’s lounge and bar" is also closed today!

I'm starting to feel deflated, but I make one last go of it and try to get into Turf, a gentlemen’s club. Prince Harry and the Duke of Cambridge have memberships here, and it has been repeatedly described as the most exclusive club in London.

Oh. that was easy – I'm in!

I saunter across parquet floors which echo the dreary hubbub of men who’ve drunk multiple bottles red wine for lunch, working hard to ensure my powerful sheux don’t make too loud a noise – I don’t want to wake the soporific clientele. The care-home magnolia walls don’t quite reek of privilege, and the art, though pretty, is the sort of bucolic English scenery you'd find in any Home Counties pub.

Unimpressed so far, I go in hunt of the fabled masculinity residing in this special place. But halfway across the hallway I’m met by three big blokes in the sort of suits that just automatically de-fuzz themselves.

"Hullo, I’m Toby Young," I say in a burp-deep voice.
"You’re not meant to be HERE," they chuckle.
"But I’m Toby Young!"

Without touching me once – who would, right now, really? – they use their burly bodies to guide me out of the unguarded entrance. Who cares? I was inside! Brief though it may have been.

I did it! I got into an all-male members' club using Young as my shield.

Now, how’s about I go to that first Office for Students meeting in his place?