Making bad taste sex jokes, staring at a woman's cleavage and faking a heart attack - there are some things you just don't do on a first date.

But no one told "Simon from Palmy".

The businessman was at the centre of last night's First Dates NZ in an episode that will surely go down as the most awkward of the series.

The show, which matches potential partners and films their first date together, followed the antics of Simon, a businessman from Palmerston North.


Simon quickly set the tone when he admitted he was looking for someone to "look after me".

"A woman would need to make my bed, and breakfast please, then I'll take you on holiday, and we'll call it even," he said.

"I'm a little bit old fashioned. I'll look after you and you look after me," he said.

Things headed downhill from there when Simon's date, 22-year-old model Carey, showed up.

When she said she wasn't drinking, Simon tried to order her "four shots of tequila - a cheap one".

Once the pair headed to a table for dinner, Simon quickly admitted he couldn't stop staring at his date's cleavage.

"I keep looking at your boobs," he said.

"Would you like me to cover them?" Carey replied.

Simon then asked her if she had sex on the first date.

"Probably not with you," she said, her awkwardness obvious.

Simon, 25, later faked a heart attack and fell to the floor because he "wanted to be resuscitated".

Despite admitting the awkwardness factor was a "strong 10," Carey had been charmed by the end of her date and admitted Simon was her type.

"He's very career driven, he's outgoing, he's very kind natured and he's passionate about life. He would be my type, I would say," she said.

But the fact that Carey had a young child proved to be the deal breaker, and the pair admitted they'd be better off as friends.

"I just feel like you're at a stage in your life where you can date someone with a child," Carey told a disappointed Simon after their date.

• Watch episodes of First Dates NZ OnDemand here.