A look at Harry Styles' dating past amid rumours of new Aussie influencer 'girlfriend' Yan Yan Chan

Harry Styles made an estimated $95 million from his worldwide Love on Tour, but the former One Direction singer may have taken more away from the tour than just an impressive pay-day.

The ‘Adore You’ singer could have been taking the name of his tour quite seriously as he reportedly enjoyed a secret getaway with an Australian influencer and fashion blogger off the back of his Sydney concert.

Harry allegedly slid into Yan Yan Chan’s direct messages while performing Down Under and the pair struck up a close friendship, with the latter being invited to a private afterparty on 4 March.

Yan Yan Chan and Harry have been mutual followers on Instagram since 2020 but had never been seen together. However, Yan Yan was spotted in the corporate box at the March Love on Tour gig with fellow influencers.

The fashion blogger was born in Hong Kong and moved to Sydney at a young age where she found success on her blog. 

While Yan Yan Chan’s most recent public relationship was with reality star Nathan Jolliffe, with the couple dating for five years before splitting in July 2022, Harry Styles has had a host of other relationships in the public eye - PeopleWorld takes a look:

Caroline Flack

Harry was first linked to the late Caroline Flack in 2011 when he was performing on X Factor as part of One Direction while she hosted the popular ITV singing show.

The Grammy Award winner was just 17-years-old when he started to date the 30-year-old Caroline, with the latter stating in her autobiography ‘Storm in a C Cup’ that she ‘already knew’ that Harry had a crush on her.

Following backlash about their age gap, the pair broke up in 2012.

Taylor Swift

Taylor Swift is known to write songs about her ex-boyfriends and what better tune to prove her relationship with Harry Styles than ‘Styles’ or ‘Ready For It’ which are seemingly about the One Direction alum.

The pair dated between December 2012 and 2013 being seen on dates around England.

Kendall Jenner

A relationship that almost broke the Internet was when Kendall Jenner was linked to Harry Styles, not once but twice, between 2013 and 2014 as well as 2015 and 2016.

The model and singer were spotted on several outings including at a New Year’s Eve party where Page Six reported the couple were ‘touchy-feely’.

Nadine Leopold, Sara Sampaio and Georgia Fowler

Kendall was not the only top model Harry Styles has been linked with over his years in the spotlight including Victoria Secret Angels Nadine Leopold, Sara Sampaio and Georgia Fowler.

While Nadine and Harry were reportedly together from 2014 until March 2015 after being seen on froyo runs, Harry moved on with Sara Sampaio before going on Scrabble dates with Georgia Fowler the same year.

Nicole Scherzinger

Harry has a knack not only for dating high-end models but also older women as he was in a reported dalliance with singer Nicole Scherzinger.

They first connected at the end of X Factor but due to the impressive age gap they did not reconnect until 2014.

Kiko Mizuhara

Harry’s penultimate relationship before his high-profile romance with Olivia Wilde was with Kiko Mizuhara.

The couple were confirmed in 2019 after Kiko initially denied not knowing the singer but was then seen at his 25th birthday party.

Olivia Wilde

The most recent connection to Harry Styles was his ‘Wilde’ romance with director Olivia, who he met on the set of Don’t Worry Darling.

Olivia entered the relationship off the back of a divorce with Jason Sudeikis and through a messy press tour with Florence Pugh and Chris Pine, Harry and Olivia ended up calling it quits last year.