Ashton Kutcher first burst onto the silver screen in Dude, Where’s My Car?, as a bit of a slacker and an unlikely romantic hero.
However, over the years the loveable Aston became not just a heartthrob, but a serious contender for the role of Cary Grant of this generation.
Having stared alongside Hollywood’s most beautiful and talented actresses, he takes on the role of Adam, who is hoping to turn his friendship with Emma (Natalie Portman) into something more... But how tight was the relationship with some of his other leading ladies?
Just Married with Brittany Murphy
In 2003, Kutcher tested the tempestuous waters of romantic comedies, playing husband to his then real-life girlfriend, the late Brittany Murphy.
In the film, Kutcher and Murphy’s Tom and Sarah marry after only a few months together and then suffer a disastrous honeymoon in Europe, during which they break up. But, as is often the case in romantic comedies, things ultimately work out for the central couple.
Verdict: A bit stretch, but with some compromises they could survive.
Guess Who with Zoe Saldana
In Guess Who, a race-reversing remake of Guess Who's Coming to Dinner?, Kutcher tried to win over the family of his black girlfriend, played by future Avatar star Zoe Saldana, including her hard-to-please father, played by the late Bernie Mac.
Verdict: A little frayed, but with potential.
A Lot Like Love with Amanda Peet
In A Lot Like Love, Kutcher stars opposite Amanda Peet as two twenty something singles who slowly fall in love through numerous, brief interactions over the course of several years.
Verdict: Hanging on by a thread.
What Happens In Vegas with Cameron Diaz
Kutcher took the plunge again in 2008's What Happens in Vegas, accidentally marrying Cameron Diaz after a drunken night in Sin City.
Complicating matters, after their night of debauchery, the newlyweds win the slot machine jackpot, leading each of them to spend the rest of the movie trying to do away with the marriage and keep all of the money. Ah, romance...
Verdict: She’s stringing him along we think.
Killers with Katherine Heigl
In the action-comedy Killers, Kutcher joined forces with Katherine Heigl to play a suburban married couple whose domestic bliss is interrupted by Heigl's character's realization that her husband is a trained assassin, and himself the target of a hit.
Verdict: Too many knots to untangle.
No Strings Attached with Natalie Portman
In No Strings Attached, Natalie Portman plays a commitment-phobic doctor who starts a strictly-sex relationship with her TV production assistant pal, played by Ashton Kutcher.
But the well-regarded Portman is just the latest lovely lady to star opposite Kutcher on the big screen.
Verdict: Strongest bond yet.