John Mayer’s Friends Urge Him to Settle Down Amid Romance Rumors with Influencer Kat Stickler

He’s a seven-time Grammy Award winner with a high-profile dating history to boot. But have John Mayer’s playboy ways finally come to an end?

From Jessica Simpson and Taylor Swift, to Jennifer Aniston and Katy Perry, the musician has undoubtedly gained a reputation in Hollywood for being a legendary lothario and perpetual bachelor.

However, it seems Mayer, 47, may have recently met his match in social media influencer Kat Stickler, 30.

This week, reports surfaced that Mayer was ‘actively pursuing’ Stickler, a TikTok star, and that he ‘sought her out and pursued her.’

Mayer and Stickler have yet to publicly address the dating speculation, though the TikTok star did post a cheeky video on Tuesday informing her fans that she’s indeed ‘single’.

Still, the singer-songwriter’s close friends are crossing their fingers that Mayer has decided to ditch his penchant for ‘fun flings’ and finally ‘settle down’ with someone special.

‘John’s friends would love to see him happy in the love department,’ an insider exclusively told the Daily Mail. ‘Fingers are currently crossed, and his friends want something to materialize with Kat.’

The relationship rumors swirled earlier this week when gossip blog DeuxMoi reported on Sunday that the Dead & Co. guitarist was allegedly spotted with the content creator, who has a combined 14million followers across Instagram and TikTok, at a private members-only club in New York City.

The two were then pictured just a day later on an apparent dinner date at another members-only club, Flyfish Club.

While it’s understood that the rumored pair are still getting to know each other, the inside source admitted that both Mayer and his friends are hoping it turns into something more serious down the line.

‘He is looking to settle down and his interest in Kat, for him at least, is to be more than a fun fling,’ they said, adding that Stickler also ‘seems to be open’ to the relationship.

‘Friends and John himself would like to fast-track this to be something serious,’ they continued. ‘He definitely has a thing for her, and his friends are hoping they meet her at some point.’

Mayer’s alleged flirty outing with Stickler appears to mark a change of heart for the ‘New Light’ singer, who has made headlines in the past for his string of celeb-filled exes.

His first high-profile romance was with Jennifer Love Hewitt back in 2002. 

While the I Know What You Did Last Summer star was rumored to be the inspiration behind Mayer’s Grammy-winning hit song ‘Your Body Is a Wonderland,’ he later confirmed on the Call Her Daddy podcast that the track is actually about his high school girlfriend.

Mayer went on to date then recently-divorced singer Jessica Simpson from 2006 to 2007. 

The pop star detailed their on-again, off-again romance in her best-selling memoir Open Book, in which she revealed they had broken up another eight times before finally calling it quits in 2010.

That final nail in the coffin, she said, was Mayer’s infamous 2010 Playboy interview in which he referred to her as ‘sexual napalm.’

Mayer then had a brief fling with model Minka Kelly in 2008, before moving on with Friends actress Jennifer Aniston – who was nine years his senior.

Their whirlwind romance began after meeting at an Oscars party in February 2008. After a brief split six months later, the pair reconciled in October that same year. They broke up for a second time in March 2009.

It was in that same Playboy interview where Mayer admitted he’ll ‘always be sorry that it didn’t last’ with Aniston, but hinted that he wasn’t ready to give up the single life just yet.

‘In some ways I wish I could be with her. But I can’t change the fact that I need to be 32,’ Mayer said at the time. 

‘I want to dance. I want to get on an airplane and be like a ninja. I want to be an explorer. I want to be like The Bourne Identity. I don’t want to pet dogs in the kitchen.’

Following his short-lived fling with Taylor Swift in 2009, when she was 19 and he was 32, Mayer was rumored to be the subject of her hit song ‘Dear John’.

Though, Swift never confirmed whether the track’s biting lyrics are about the fellow musician.

One of Mayer’s longest public relationships was with pop star Katy Perry, which began in 2012 and lasted on-and-off for three years. 

The pair collaborated on the song ‘Who You Love’ from Mayer’s Paradise Valley album in 2013, while Mayer played guitar on ‘It Takes Two’ from Perry’s Prism album that same year.

Despite his string of public makeups and breakups, Mayer has since kept many details about his love life private.

Most recently, he’s been romantically linked to 25-year-old actress Kiernan Shipka since 2022, with the pair being photographed together on multiple outings. 

But just last June, Mayer revealed that he’s in fact single and looking for the one.

‘I’m older now. It’s been a very long time since I had my own situation. I stay inside the house. Aren’t I a good boy, America? I’m not dating anybody!’ he said during a live SmartLess podcast event on June 12.

Shockingly, Mayer also made the public declaration that he’s ‘absolutely’ ready for marriage.

‘I would not date someone if it didn’t have the upward mobility of becoming a marriage,’ he told co-hosts Will Arnett, Jason Bateman and Sean Hayes at the time. 

‘Every girlfriend would be a potential wife at this point.’

This wasn’t the first time Mayer has expressed his newfound desire to become a husband and a father. 

In 2021, he told pal Andy Cohen that starting a family is the last item he wants to check off on his bucket list.

‘There’s one thing left and that’s wife and kids,’ he said on SiriusXM’s Radio Andy at the time. 

‘That would complete all of it, and I thought about this as recently as last night. ‘Cause my brothers are both married and have children.’

Indeed, our inside source confirmed just as much when they told the Daily Mail that Mayer is ‘putting in the time’ with Stickler to see if their relationship could potentially go the distance.

‘John is talented, charming, funny, handsome and an all-around nice guy. When you are in his orbit, it is very hard for people not to like him,’ the insider said.

‘For women, that goes tenfold. He’s chosen to be with some amazing women in the past, but everyone he’s dated or had a fling with, it was just that.’

The source also shed light on why Mayer, who received quite a kiss-and-tell reputation after his notorious Playboy interview, has decided to keep his love life out of the spotlight these days.

‘In the past, he was more of an open book and wouldn’t mind when people would talk about his playboy dating ways – he wore it as a badge of honor. But now, he is looking to settle down,’ they explained.

As for Stickler, the Florida-based social media influencer rose to internet stardom when she began making TikTok videos with her then-husband, Mike Stickler, during the Covid-19 pandemic.

The two were married in 2019 and announced their divorce in early 2021. They continue to co-parent their daughter MK, four.

Prior to sparking romance rumors with Mayer, Stickler was in a relationship with The Bachelorette alum Jason Tartick, but the former couple called it quits in October 2024 after less than a year of dating.

While it’s still early days for Mayer and Stickler, it may be only a matter of time before devoted fans of the singer-songwriter will see the legendary bachelor finally settle down.

‘John would like for this go-around to be something different, but we’ll see since it is so new,’ the source said.

‘If John is happy, everyone else will be happy for him.’

The Daily Mail has contacted representatives for Mayer and Stickler for comment.