Max George dated Stacey Giggs and Michelle Keegan before reportedly setting his sights on Maisie Smith.
The EastEnders star, 21, who met Max, 33, on Strictly Come Dancing, was said to have been seen snogging The Wanted singer on a flight to Crete - shortly after Max split with Stacey.
The singer and the ex-wife of footballer Ryan Giggs, 42, called time on their romance for the second time just four months after the pair reconciled, according to reports.
Max was first reported to be dating Stacey back in 2018 – when he moved in with the ex-WAG and her two children in Manchester.
Stacey was previously married to Wales international Ryan in 2007, but they split up in 2017 amid accusations that he had been having an affair.
The now ex-husband and wife share two children – Libby, 19, and son Zach, 15 – who Max took under his wing after moving in with his beau.
In 2020 the singer said he'd "never felt so strongly about anyone".
However, the couple briefly split up in March this year, before getting back together a month later with Stacey supporting Max at the funeral of his friend and bandmate Tom Parker after his tragic death from cancer.
Despite this, friends of the couple said they had parted ways once more earlier this month.
"Max and Stacey are no longer together. They had a great relationship but as time passed, they realised it wasn’t to be," a source told The Sun.
"They are both being very adult about it and it was as amicable a split could be. Max and Stacey only wish the best for each other going forwards."
Before shacking up with Stacey, Max was engaged to Coronation Street actress Michelle Keegan.
The singer proposed to Michelle in 2011, but they split just a year after he popped the question.
The picture-perfect couple were together for three years, but Max admitted that by the end of the relationship Michelle wasn't making him happy and he turned to drink.
He blamed his boozing for ruining their relationship, which led to their break-up.
Speaking to The Sun, Max explained: "I had a real problem with drinking too much and that was, without doubt, the downfall of our relationship.
"I was drinking more to forget the fact I was with someone who wasn't making me that happy."
There were reports that cheating had occurred, but Max insisted their was "no betrayal".
"It was a whirlwind," he surmised.
"I don't regret it because you shouldn't regret anything you do. You learn."
