Soleil Moon Frye

Jared attended the premiere of Vanilla Ice's movie Cool as Ice (yes, you read that right) with Soleil Moon Frye — better known as Punky Brewster — in 1991. The two were rumoured to have dated that year.

Cameron Diaz

Jared and Cameron carried on a relationship [5] from 1999 to 2003, and at one point, they were rumoured to have been engaged [6]. After their split, Cameron went on to date Justin Timberlake [7], Paul Sculfor, and Alex Rodriguez, and in 2015 she wed Good Charlotte rocker Benji Madden in a surprise ceremony.

Ashley Olsen

Jared and Ashley seemed to have had an on-off friends with benefits sort of thing over the years; they were first linked in 2005 after being spotted on a date in LA, but came back together in 2008 when they were seen holding hands and "making out" at the Art of Elysium Gala [8] in LA. An eyewitness told Us Weekly at the time that they "looked like a couple," but a source close to Ashley insisted they were just friends. Cut to 2011, and the "friends" were reportedly seen enjoying a "very flirtatious meal" at the Polo Lounge [9] in Beverly Hills.

Lindsay Lohan

Jared and Lindsay were linked when they worked together on the controversial biopic Chapter 27, for which the actor famously put on 50 pounds to play John Lennon's killer, Mark David Chapman. The movie came out in 2007, and in an interview with MTV [10] that year, Jared admitted that he "didn’t speak" to Lindsay (or anyone else) on the set while filming.

Paris Hilton

Jared was connected to the heiress in 2008 after a photo of the two making out at a party [11] during the Sundance Film Festival made the rounds. A source told Page Six that the two were "not dating seriously," but that it wasn't the first time they had made out, adding, "She likes him and she thinks he is really sexy and fun."

Isabel Lucas

In 2009, Jared was photographed hanging out with Australian actress Isabel Lucas [12], who had been previously linked to Shia LaBeouf [13] and Adrien Brody [14]. Multiple sources reported that the two were romantically involved.

Chloe Bartoli

Jared reportedly struck up a romance with his wardrobe stylist, Chloe Bartoli, somewhere around 2013. The two had been — and still are — close friends, and Chloe was even seen out with Jared the day after he won his Oscar [15] in 2014. Chloe, who also used to date Scott Disick, made headlines when she was spotted with the father of three in the South of France; photos of them cuddling at the beach [16] were allegedly the reason why Scott's longtime girlfriend, Kourtney Kardashian, broke up with him [17] in July 2015.

Lupita Nyong'o

Jared's love life was thrust into the spotlight in early 2014 as he took award season by storm with fellow nominee and breakout star Lupita Nyong'o. After the two were caught chatting during the Critics' Choice Awards in January, it wasn't long before rumours of a mutual attraction (and possible hookup) between the two started swirling — and we totally started shipping them [18].

It was never confirmed or denied whether Jared and Lupita actually sealed the deal, but their chemistry was undeniable, whether they were presenting together onstage at award shows or hanging out at Paris Fashion Week together — Jared famously referred to the 12 Years a Slave star as his "future ex-wife" during an acceptance speech. We're still rooting for them.

Miley Cyrus

In February 2014, Us Weekly reported that Jared and Miley were "hooking up." Sources told the outlet [19] that the singer "stayed over at his house" and gave some insight into their shared interests, saying, "They like to have a good time, they love to talk about art and music — and they're both comfortable with nudity!"

Katy Perry

After splitting from John Mayer [20] in February 2014, Katy Perry [21] was linked to a number of famous guys, including Robert Pattinson [22], Diplo, and Jared. The two were rumoured to have hooked up at Coachella in April of that year, with a source telling OK! [23] that the singer "has a thing for shaggy music eyes," adding, "his eyes melt her." Us too, honey.

Valery Kaufman

In June 2015, People reported that Jared was romancing 20-year old Russian model Valery Kaufman; the two were spotted hanging out in NYC [24] while Jared was busy filming Suicide Squad. Neither Jared nor Valery's reps commented on the relationship rumours, but Jared wasn't in attendance when Valery stomped the runway at the Victoria's Secret Fashion Show that November.