It's probably the most awkward question you can ask a few months into a new relationship, "how many people have you slept with?"

If the answer is not many, it can look like you're still on your training wheels, or very god fearing; a lot and new partners might feel they've latched onto a Lothario.

What many people might not do is admit to sleeping with 100 partners, rank them in order, travel the world to find the most memorable and then make a documentary about the experience.

"I'm not advocating being a slut as a lifestyle — simply sleeping with lots of people — because that's wrong, but if you meet people you fancy you should be able to enjoy being together in any form you want," Kiwi filmmaker Paul Oremland told


"For me, having had sex with lots of people, I've met some amazing incredibly wonderful people and it's been an enriching experience."

His sex life has taken him to Buckingham Palace, he's been held up at gunpoint and it's seen him sleep with everyone from gangsters to porn stars.

In the documentary 100 Men, which screened at the Auckland Pride Festival this month, Mr Oremland catalogues and attempts to track down 100 of his sexual partners.

He then lists them by their most memorable characteristics: "72: Grant the Aussie; 48: The Dublin Boys; 39: Russian security guard; 33: Footballer."

"Each of those numbers has whole stories behind them. The Albanian gangster I met four or five times in a sauna; he was off his face on cocaine and because he was speeding we would always chat afterwards.

"He was part of a gang involved in drug running and prostitution and the sauna was his escape. He was completely closeted and said if his gangster friends knew where he was they would kill him."

It wasn't the only dangerous liaison. After one encounter a gun was held to his head and he was robbed, an experience he managed to get away from unscathed.

After four decades of having sex, some of the encounters short, it was a challenge tracking people down.


"With the opera singer, I only knew that he was called Panos, so I Googled 'Greek opera singer Panos' and sent a message on Facebook. I told him we met 15 years ago, had a brief fling and was there any chance I could talk to, and amazingly he said yes."

Several wanted nothing to do with it: "One was a headmaster, he's out and married and they have an open relationship but there's no way he wanted to talk about it."

Paul Oremland with three of his previous sexual partners. Photo / supplied
Paul Oremland with three of his previous sexual partners. Photo / supplied

Another was from the hardscrabble suburbs of western Auckland.

"The westie really did have furry dice in his car and when his bros called, he would talk in this lingo.

"He was desperate to get married, have kids and a white picket fence. He took more and more drugs, went off the rails and ended up HIV positive."

Mr Oremland, said a root to remember took him to the Queen's home.

"I ended up in Buckingham Palace and he actually worked directly for the Queen. He said she had an amazing sense of humour. But the Palace was a bit of a let-down, it was like below stairs at Downton Abbey, it wasn't very glamorous. Even the cups and saucers were mismatched."

Despite counting down from 100, Mr Oremland said the documentary was not a celebration of quantity over quality. Indeed, he's no stranger to long-term relationships.

"Over 40 years, it's only two or so a year. It's never been about numbers, it's about meeting people."

Besides, he said, many people are glued to dating and sex apps nowadays and if they totted up their sexual encounters over a similar period, they might be surprised.

"The sex is more interesting when it's about more than just the sex. It's one of the reasons I don't do millions of orgies or chef sex (orgies fuelled by drugs) because that's not even sexy whereas getting to talk and knowing them is far more exciting."

The countdown acts a lens to see how life has changed for gay men and relationships over 40 years, from illegality to acceptability via the pain of HIV and AIDS.

"Now, there is the possibility of being respectable but with that comes the pressure to conform (to heterosexual ideals) which was never an option for myself as a young gay man. We were outsiders, I was sent to see psychiatrist and I was queer bashed.

"I want to be equal but I don't want to be the same. There is a danger having fought to create a sense of identity, we now sink into invisibility."

Mr Oremland said his unabashed celebration of his sex life hasn't always gone down well at screenings. It's often younger gay people who've found it confronting.

"There was this young guy in LA who said (the doco) was how gay people used to live before we were seen as normal. It was the wrong thing to say surrounded by older gay men."

He said 100 Men had been a personal journey and, overall, the reaction had been "amazing".

But he conceded, the forthright nature of the documentary, meant he's shied away from showing it to everyone he knows.

"My mum hasn't seen it. She knows about it, she's glad it's doing well but she hasn't asked to watch it."