The blurb for the show sounds like it has been plucked from an essay, writes Gemma Collins. "With intense vulnerability and troubling honesty, comedian Simon Amstell explores freedom, joy, love, death, adventure, art, peace, sex, regret, success, eating, suffering, dreaming, healing, forgiving and other areas."
All that's missing is "discuss".
Perhaps the man himself can shed light on the ludicrously long explanation of his latest stand-up show, To Be Free?
"Well. Okay. So. It's an attempt to be free – an attempt to transcend my own ego – which keeps me from being completely free in my life," he says.
"I still have this need to be a special and fascinating person. I'm also imprisoned by my insecurities and my fears of the culture I'm in.
"Ideally, I want to be able to say and do what I want all the time, like I can on stage. That doesn't exist off stage – it doesn't. So things happen and that causes me problems.
"The show is about that. It's about letting go of all that nonsense and coming to the place where I am."
That's very deep, Simon.
"And that's the sort of show it is," he laughs.
"It's full of all those things listed. Sex, drugs and the terrible situations I find myself in.
"I get there through poking at my ego and what happens to me as a result of that lunacy."
The stories are mainly from the past couple of years, he says – experiences accumulated since his stand-up show, Do Nothing. "Plus memories from my traumatic childhood that I bring up and exploit for comedy," he chuckles.
Like your BBC2 sitcom, Grandma's House, for instance?
"Yes. But – I've actually been doing stand-up since I was 13," he explains. "I was part of the Harlequin Theatre School's annual charity show.
"I really liked hearing the laughter and thought, 'I want to do more of this'.
"Stand-up is at the root of all things I've ended up doing. I never abandoned it. I only ever break from it when something needs to be written."
So popular has his To Be Free show been, he recently sold out residences in New York and London.
"I've just got back from New York and LA, promoting the American leg of the tour, which begins in April – once I've finished touring over here in March," he says, plugging away.
"I was in New York for two months, at Theatre 80 St Marks. It was really fun – new people coming to see me, and me being a new person on the scene to them."
Being successful in a "new place" has helped inflate Simon's ego all the more.
"It feels like I must definitely be funny, to be received there," he says. "It feels like I haven't got away with something – not that I've thought that about people coming to see me in the past."
He pauses.
"When I started this tour in London, it seemed the people who were there really understood what I am as a comedian. No-one was expecting it to be something it's not."
Something that it's not? Does he think people expect to see the Simon who made his name asking pop stars some very awkward questions on shows such as Popworld and Never Mind The Buzzcocks?
"That is what I mean, I think. They're not two people, essentially."
Simon has won two British Comedy Awards, an RTS Award, a Broadcast Award, a Chortle Award and has been nominated for a Bafta. He's well- respected, that's for sure.
"How do I feel about Buzzcocks now?" he says. "I don't think about it too much. And no, I don't watch it.
"It's generally what happens. Once I start something new, I don't know what the hell I'm doing. So I figure out what I'm doing, I get bored and then I leave," he laughs.
"That's how it goes.
"With my sitcom, I started out not knowing how to write a sitcom, not knowing how to act and not knowing why I felt so anxious around my family.
"I learned how to write, how to act and now I understand my family, I feel at ease with them. There was no need to do it any more."
It's funny to think of Simon Amstell as anything but a star. But if you cast your mind back to 2003 and the Leicester Mercury Comedian of the Year competition, he was a relative unknown in the world of stand-up.
It was a line-up you'd pay big bucks to see now, including Greg Davies and Rhod Gilbert, all battling it out for the coveted prize.
A memorable occasion, you'd think.
"I was in it, was I? I must have been about 17 then. No. I was 22.
"There were so many of them and I never won any. It was a year of competitions I lost. I should have waited to do those things."
Simon, according to one of the judges, was ill-at-ease as a stand-up back then. "It's my act," he protests. "Everyone in comedy is – it's the reason you become a stand-up.
"Someone dumped me for that once, so I know this is true," he admits. "This has been rectified with a lot of therapy and healing plant medicine.
"I look relaxed now – even when I am ill-at-ease," he says.
So what does he think of Dave's Leicester Comedy Festival? "Have I been to it before?" he asks.
Well, it's a big thing here, we tell him. It's been going for 22 years and Curve theatre, that's a decent enough venue to play.
"Great," he says. "The truth is, my tour happens to be coming through at the same time.
Oh. "Will you be there to laugh at me?"
*Uncomfortable silence*
"Good luck with everything in your life," he says.
Simon Amstell plays Curve on February 10, at 8pm. For tickets, see www.comedy-festival.co.uk
He's also bringing his show to Loughborough Town Hall, on March 4. www.loughboroughtownhall.co.uk