The first time she tried this method was a spur of the moment decision. She was walking past some terrace houses in Ultimo by herself at 10pm when she encountered a group of men drinking on a door step. One of them yelled out to her and when she removed her headphones and walked back to him, his bravado faltered.
As Ms Gordon-Smith describes it in Honi Soit, "it was an act of performance for his mates who assumed and hoped I'd ignore it".
"Catcalling places women in the same category as statues to p**s on or walls to tag - inanimate public property over which dominance can be asserted by groups of men sitting in the street."
After she spoke to him, ignoring his friends in the background who were averting their gaze and sniggering into their beers, she left, and he mouthed the word "sorry" quickly and silently so the crew behind him would never know. And that is the moment that sparked her interest and spurred Ms Gordon-Smith on to explore this issue further.
"I started to I wonder what would happen if you just had the one-on-one conversation with other people who do this, and would it be possible to change their behaviour? I thought it would make good radio," she told news.com.au.
And she was right. It did make good radio. So much so that Ira Glass picked it up for his popular This American Life podcast series:
Eleanor Gordon-Smith, a reporter in Australia, confronts her catcallers in King’s Cross to figure out why they do it. As...
To get the sound bites Eleanor ditched her spectacles, popped on some red lipstick and a pair of heels and spent hours walking around Kings Cross late at night, engaging with the men who called out to her.
She went out six times, and says she was catcalled at least five or six times on each occasion.
While she presumed that the men would be "sexist nutjobs", she was surprised to find "they didn't seem unreasonable, they weren't hard to talk to".
She was also shocked to discover that most of the men genuinely thought that women enjoyed being catcalled.
One man said: "[girls] love it ... they have to ... it's a nice thing when a man says hello." Another said: "I'm just trying to make women have fun."
Ms Gordon-Smith decided to take up the challenge of convincing the men that actually, most women hate it when a strange man yells out to them.
"I just thought, 'this can't be where that ends because that's nuts ... Please listen to me while I tell you that's wrong'.
"It occurred to me they've just made a mistake, they've just got some kind of central fact about women wrong and they think that we really enjoy this. Surely I can stand in front of these reasonable caring dudes and just say 'women don't like it' and that might be a way of talking them out of doing it ever."
Despite her impressive powers of persuasion (Ms Gordon-Smith has had extensive international debating practice) and calmly presenting them with stats - such as the fact that 85 per cent of women say they feel "angry" when they are catcalled - she largely failed in her quest to change men's minds.
Though there was one success story.
Zach, who is the main focus of the This American Life podcast, yelled out "hey luscious lips" as Ms Gordon-Smith walked past.
After engaging with him she learned that he regularly runs up to groups of girls when he's out and slaps one of them on the backside.
He refused to believe that a girl would see this as anything other than a "bit of fun".
Ms Gordon-Smith met up with him at 5pm on a Wednesday evening in the same spot to try and convince him to change this behaviour. She asked him how he would feel if someone slapped his arse and he said he would "feel a bit special".
After sitting in a gutter in Kings Cross and speaking to him for more than two hours and explaining how that sort of behaviour makes women feel, he shook her hand and promised that he would never slap a girl's backside again.
On the day news.com.au spoke to Ms Gordon-Smith, Zach had sent her a "really touching message" saying that a friend had sent him the link to the This American Life episode and he was glad that she had opened his eyes to how wrong his behaviour was.
While Ms Gordon-Smith is thrilled with this outcome she is quick to point out that she doesn't recommend other women "try this at home".
"I don't want to suggest people by themselves in back alleys should start arcing up," she says.
"I was fortunate enough to have the resources to do this safely."
Despite her precautions, such as texting a friend to say where she was and that she was OK, there was one instance where she felt uncomfortable.
It occurred when she encountered a group of "violently unpleasant" men a couple of times in the same evening.
"As they got drunker they backed me against the doorway and they were standing in a horseshoe around me - I started to become aware that I was in a situation that I couldn't necessarily get out of," she recalls.
While that was one of the darker experiences, she did find it amusing when one man yelled "Feminist! Feminist!" and ran away when she tried to engage with him.
The main thing she learned from this project is that it's incredibly difficult for one female (who has no relationship to the male) to change their behaviour. So she's asking men who know catcalling is wrong not to stand by and be complicit.
"It's hard for us to change their minds ... their male friends are far more efficient to stop it," she explains.