Harry Styles' Girlfriends: Taylor Swift, Kendall Jenner, and Others

Strap in, folks, because this one's gonna really stretch out for a while -- we're looking at Harry Styles' love life!

We all know the former One Direction member knows how to sing about the ups and downs of relationships, and he's written plenty of hits about that exact subject over the course of his career.

The thing is, some of his relationships have been just as dramatic and dynamic as his songs -- let's check them out!

Styles was thrust into the public eye when One Direction was introduced through performances on "The X Factor" -- and he ended up briefly dating television presenter Caroline Flack, who had hosted its spinoff, "The Xtra Factor."

The pair received much attention for their 14-year age gap, and they ultimately went their separate ways after just a few months.

Styles was later linked to model Emma Ostilly, who appeared in the music video for One Direction's track "Gotta Be You," although their fling ultimately proved to be brief.

The performer subsequently started seeing Taylor Swift in 2012 ... and although they took several trips during that year's holiday season, they broke up in January 2013.

The "Watermelon Sugar" singer has spoken fondly of his ex in the years since their romance fizzled out, and he told Howard Stern the hitmaker was a "great songwriter."

Styles moved on with Kendall Jenner ... the couple was first spotted in each other's company while having dinner in West Hollywood in 2013.

Rumors about the pair -- who maintained what appeared to be an on-off fling -- swirled for several years, during which they were seen with each other on various outings.

Styles stayed busy in the interim, though, as he was linked to models Nadine Leopold and Georgia Fowler ... although neither fling lasted for very long.

The singer eventually reconciled with Jenner in 2016, and her sister Khloe told Entertainment Tonight that, while she didn't know if the two were "like boyfriend-girlfriend," the singer and the model "were in St. Barts together hanging out, so to me that's dating."

Although Styles and Jenner were later seen with each other during her 21st birthday party, their romance appeared to come to an end ... but they've stayed on friendly terms ever since then.

Following his split from Jenner, the singer started seeing model Camille Rowe, and the fashion industry figure was photographed attending several of the performer's concerts throughout 2018.

The two attempted to keep their relationship under the radar during its length, and following their split that year, Styles included a voicemail from his ex at the end of his song "Cherry."

Styles then began the arguably most high-profile of his romances when he started dating Olivia Wilde, whom he met when he was cast in her 2020 film "Don't Worry Darling."

The singer and the actress -- who was formerly engaged to Jason Sudeikis -- first set off the rumor mill after they attended a wedding together in 2021, and they started being spotted together during his concerts, as well as on various getaways.

The pair, who had a 10-year age gap between them, garnered much attention for their romance over the remainder of 2021, and a line from Styles' track "As It Was" -- "leave America, two kids follow her" -- appeared to be a clear reference to their romance.

However, cracks between the two began to show over the course of 2022, and when their split was announced that November, a source told People the pair had come to a "very amicable decision" about ending their romance.

Styles eventually moved on with Emily Ratajkowski, and the two were snapped locking lips during a trip to Tokyo that took place in March of 2023.

Although a source told People at the time that the supermodel was "interested in seeing him again," the pair's fling proved to be brief.

Styles was later linked to actress Taylor Russell, with whom he was first seen in June 2023, and he attended the opening night of a stage production of "The Effect."