Jack Antonoff, 2001-2003
Given her side career as a singer, it only seems natural that Scarlett dated the Steel Train frontman. The two got together when the Ghost World star was just out of high school, but after an apparently bitter split, the musician blasted her in one of his songs a few years later. Ahh, young love indeed!
Patrick Wilson, 2004
Both were nominated for Golden Globes—he for Angels in America and she for Lost in Translation and The Girl With the Pearl Earring. But while they didn't attend the ceremony together that year, Johansson and Wilson were a hot, if brief, item.
Jared Leto, 2004
A year after earning major accolades (and showing off that fantastic bum) in Lost in Translation, Scarlett turned heads when she hooked up with the 30 Seconds to Mars frontman. While the romance didn't last, the pair did reunite at the 2012 Democratic National Convention, where they cozied up to each other.
Benicio Del Toro, 2005
Speaking of awards show bashes, Johansson reportedly got hot and heavy with the Usual Suspects star in an elevator after the Oscars. After failing initially to deny the story, she later called it a joke, only Del Toro didn't get the memo, telling Esquire coyly, "Let's leave that to the imagination. Let's not promote it."
Josh Hartnett, 2006-2007
These two were lovebirds for a little more than a year and were out in the open about it, having once been spotted canoodling at a London nightclub. But the usual work commitments got in the way, and, well, they broke up in 2007, much to the delight of Scarlett's many male admirers.
Ryan Reynolds, 2008-2010
Scarlett and Ryan seemed like the picture-perfect Hollywood couple. Very much in love, the twosome nonetheless had a hard time finding time to keep the flames going, given their ever-busy schedules. The two amicably separated two days before Christmas in 2010, and their divorce became final the next year. While he went on to marry Blake Lively, she went on to date...
Sean Penn, 2011
Despite their 24-year age difference, the stars had lots in common, like jogging, humanitarian work and a love of Cuban food. Alas, the sparks didn't last.
Justin Timberlake, 2011
The bombshell was rumored to have had a brief fling with J.T., for whom she previously starred in the music video to his hit "What Goes Around Comes Around." Of course, Timberlake ended up tying the knot with Jessica Biel, but we can't help imagining what could've been.
Nate Naylor, 2011-2012
The two had been dating for some time before ScarJo went public with her relationship with the 38-year-old advertising executive in January 2012. But things went south and they parted company 10 months later.
Bradley Cooper, 2012
Scarlett struck up a brief romance with her He's Just Not That Into You costar while the latter took a time-out from on-again, off-again girlfriend Zoe Saldana.