The 5 million copy
bestselling series

At some point, everyone needs to bluff it to make it. To prove our point, we ask celebrities about their biggest bluffs. Approach the bench…

Toby Young



Writer and columnist Toby Young started academic life by accepting a place at Oxford University which he subsequently learnt was offered as a result of a clerical error. He went on to get a first in Philosophy, Politics and Economics (PPE), which proves that he can bluff with the best of them.

He later co-founded the 1990s anti-establishment arts and culture magazine, Modern Review, and was then hired (and later fired) by Vanity Fair magazine in New York. He wrote a book about the experience called How to Lose Friends and Alienate People (which was made into a film).

He is currently associate editor of The Spectator.



Toby Young explains…

  1. Gravity – A useful quality to be able to conjure up when making restaurant bookings over the phone.
  2. Les Miserables – A film I would rather stick pins in my eyes than see.
  3. The Eurozone Crisis – The nail in the coffin of the federalist project – hopefully.
  4. The Off-side Rule – Something I try to explain – unsuccessfully – every other week to my four children aged 9, 7, 5 and 4 when we’re sitting in the family stand at Loftus Road watching Queen’s Park Rangers.
  5. Serendipity – That moment at the end of each football season when I discover that, contrary to expectations, QPR haven’t been relegated after all.
  6. Oprah – An emotionally incontinent chat show hostess.



Have you ever gotten something for nothing?

Yes. In 1987 I was asked by a cashpoint machine in Cambridge, Massachusetts, if I wanted any more money. This was in spite of the fact that I hadn’t inserted my cashpoint card. I said ‘yes’ and when it asked me how much I said ‘$400’. Four hundred dollars then appeared. After that, a card popped out and I realised it belonged to the person who’d used the machine before me and the $400 had come out of their account. I kept the money for a couple of days, but was then overcome by guilt and returned it to the bank.

To whom, or what, do you owe your big break?

Julie Burchill was quite kind to me when I was starting out in journalism. She’d just left her then husband Tony Parsons and moved in with Cosmo Landesman, my next door neighbour. So she was literally the girl next door.

Where and when was the last time you felt entirely out of place?

In February of this year I drove from Gilgil to Ramaruti in Kenya to see a Catholic priest about starting a primary school. I encountered an impromptu road block in a town along the way erected by some disgruntled townspeople because a taxi driver had been murdered the day before and they weren’t happy with the police’s response. My car was surrounded by a drunken mob and for a second or two I thought it might get ugly. Luckily, I was with a friend who spoke Swahili and he defused the situation.

When was the last, or the first time you bluffed your way into an event you weren’t officially invited to?

At the Conservative Party Conference in 2010 I gatecrashed the News International party. That was a lot of fun and something of a last hurrah because pretty soon afterwards neither the Conservative Party nor News International wanted anything to do with one another. I don’t suppose there’ll be another NI party at the Tory Party Conference for a while.

When would you advocate bluffing it?

When you’ve run out of other options.

Have you ever bluffed your way into getting a date?

I don’t think I’ve ever got a date that didn’t involve some sort of bluff. In my experience, the best way to bluff a girl into bed is to tell her you really fancy her and, if only you’d met her a week earlier, you would definitely be interested in her. But unfortunately you’ve just started seeing someone else. Works every time.

What is the best lie you ever told?

When I proposed to my wife for the first time I offered her a diamond ring. She said no, but then asked how much the ring cost. I exaggerated how much I’d paid for it eightfold. I thought, ‘She’s said no, she’ll never find out the truth, what harm can it do?’ At that point she asked to see the ring again and tried it on. She then held it up to the light and began to admire it and I thought, ‘Oh God. What if she changes her mind and keeps the ring? Sooner or later she’s going to find out I lied about how much it cost.’ From wanting her to say yes, I was suddenly desperate for her to say no.

And, what is the best lie you never told?

I eventually confessed to my wife which I think was the right thing to do. We were married by that time, of course.

Have you ever committed, or witnessed, a major bluffing fail?

Yes. When I was living in New York in the late-90s the hottest restaurant in town was Balthazar, owned by Keith McNally. In order to get a reservation you had to call this secret VIP hotline and only a few people had the number. I managed to persuade the fashion director of Vanity Fair to give it to me and I called it and asked if I could book a table that Friday night. The person on the other end asked how I got the number and I said, ‘Keith gave it to me.’ ‘This is Keith speaking,’ came the reply. ‘I didn’t give you this number.’ I didn’t get a reservation.