It was a supposed chance meeting in a bar, which led to Kim Kardashian asking someone out herself for the first time ever.
But when actor Michael Copon tried to move in for a kiss on their date, the famous reality star turned the tables and played hard to get.
Kim ended up pulling away, only allowing him to kiss her on the cheek as they stood on her hotel balcony following a lunch-time date.
Moving in: Kim Kardashian is seen here pushing actor Michael Copon away as he tries to kiss her on the lips on her hotel balcony following their date, screened last night in the season premiere of Kourtney and Kim Take NY
Amorous intent: But she did allow him to give her a kiss on the cheek after rejected his initial advances
The scenes were shown in the season premiere of Kourtney and Kim Take New York on U.S. channel E! last night, which follows the sisters as they prepare to open their clothing store Dash in the city.
Clearly looking for romance in the Big Apple, Kim informed viewers that she was 'newly single and I've never taken the chance to be single.'
Kim runs into Copon - an old actor friend who she starred alongside in 2009 TV series Beyond the Break - while on a girls night out with Kourtney and another friend.
A toast: Kim and Michael went for lunch at Serendipity, the reality star's favourite restaurant
Celebrate! Kim leaps in the air with joy after Michael accepts her date invitation when she called him up. She claimed it was the first time she had ever asked anyone out herself
But things got a little tricky for Kim when Copon, who has also starred in Hawaii Five-O and starred in the 2001 movie Power Rangers: Time Force, failed to ask her out.
She told Kourtney: ' I don't chase people. I've just been dropping hints that I'm single.'
However, after some persuading, Kim ended up calling the actor and going out for dinner.
'I can't believe I've had the balls to call Michael and ask him out,' she shrieked.
Cosying up: Scott and Kourtney get close on the first episode of the show, with Scott being asked to move back into the hotel suite by his long-term girlfriend
Three's a crowd: Kim was initially unimpressed at her sister's decision to move Scott into their hotel suite
But while Kim was taking things one step at a time, her sister Kourtney couldn't keep her hands off her baby daddy Scott Disick with the pair sharing frequent kisses and affectionate exchanges - right in front of Kim.
Disick was clearly seeing the move to New York as a chance to turn over a new leaf after his occasionally troubled appearances in previous spin off Kourtney and Khloe Take Miami.
'This is my city. I am thinking I can really improve myself here,' he said.
And things certainly seemed to be going well for the couple, with Scott soon being invited to share Kourtney's hotel room suite, much to the annoyance of Kim, who was hoping to 'bond' with her older sister.
Sisterhood: A dressed up Kim and Kourtney enjoy a night out together in New York, where Kim is on the look out
'I thought we were moving out here together,' she complained.
However, the sisters soon sorted out their differences in the less-than-dramatic episode, with Kourtney promising Kim she'll make an effort to include her in the future.
Earlier in the show the Kardashian sisters invited Kanye West to their Dash premises in the city's trendy SoHO district for some style advice.
A little help: Kanye West pops in to Kourtney and Kim Kardashian's New York Dash store to give the sisters some style advice on the first episode of the show
Style guru: The rapper 'randomly' stopped by the Kardashian's store in a pair of shades and black suit
Viewers of the show, which sees the sisters opening the New York branch of the clothing store, saw the rapper flirt with Kim as he looked over plans for the shop.
Looking cool in a pair of aviator sunglasses and a black suit, the rapper was a bit surprised at the news that the sisters intended to open the store in two weeks.