Top 9 Mary Kate And Ashley Movie Love Interests, Ranked

The adventures of blonde twins Mary Kate and Ashley captivated the hearts of kids and tweens worldwide. The end of their collective escapades in 2004 dismayed fans, but the legacy of the iconic twins lives on in their best feature and direct-to-video movies where they were up to no good, with the help of some lovable boys, of course. Apart from the twins sticking up for each other as siblings, their love interests were the hottest highlight in the movies.

The girls said in a meta moment in 2003’s The Challenge: “Boys may come and go, but we’ll always have each other, and that’s not just in the movies”, but they sure were invested in the dreamy yet intriguing boys they would meet during their travels to Paris, London and New York. There were a few of their fictional boyfriends who stood out when it came to their story arcs, their interest in the twins’ lives, and how much they added to the movies.

9 Jean – Passport To Paris (1999)

Jean was a charming French boy who loved showing Ally around in Paris, and the fact that he was in a band with Michel was also attractive to the tween Ally, played by Ashley Olsen. The twins weren’t able to go to their Spring Fling dance; to their horror they were asked to spend their summer in Paris.

Acted by Brocker Way, Jean was nice up to that time he stood up and yelled at a French waiter to get Ally ketchup on the side of her dish, which will never be cool or romantic.

8 Jim – New York Minute (2004)

The last ever Mary Kate and Ashley movie meant that the men in these movies were the very last romantic interests of the uber popular girls! Jim the bike messenger kept running into Ashley’s Jane over and over again, which was serendipitous at best.

Apart from this, he lacked any real personality that fans could spot. His bicycle was the biggest defining feature about him, and his spiky blonde hair too. However, Jim did take Jane on some fun bike rides, making him a great buddy to have in a big city.

7 Lord James Browning Jr. – Winning London (2001)

The twins were always traveling all around the world, so when they landed in London it was but obvious that they would find someone to fall for, temporarily. While attending their international Model United Nations event, Mary Kate’s Chloe met James Browning, the son of a British nobleman.

While a suit-sporting, well-mannered gentleman is always welcome, especially by young starry-eyed girls, James was a bit of a sore loser against Chloe at polo. His polite British manners did make up for this flaw, though.

6 Jordan Landers – Holiday In The Sun (2001)

The problematic diver of one of the best Mary Kate and Ashley movies was involved in some criminal activities, but he was interesting, at least. His first date with Alex (Ashley) involved them feeding sting rays at his aquarium office in the Bahamas, and he also sang a song that he wrote for her in front of an audience, which was lovely of him.

Things get really exciting when audiences found out that he’s actually smuggling vintage pieces to the Bahamas, which made them all end up in jail! Still, the scuba-suit-wearing Jordan was a fascinating (if not the most wholesome) love interest of the Olsens.

5 Paolo – When In Rome (2002)

Everybody loves a holiday crush, and Paolo fit the bill nicely. The Italian may have little regard for Charli’s (Mary Kate Olsen), job and could have a hand in her getting almost fired, but this was shown as down to the fact he wanted to spend time with her.

He also was ambitious and motivated — Paolo wanted to become a famous chef and baked some really great pizza too. Considering how young Mary Kate and Ashley were, their love interests were young, too, so it was nice to see a more mature and goal-oriented guy after Charli’s heart.

4 Greg Jeffries – Switching Goals (1999)

The very epitome of schoolyard young love, Greg was a sweet kid who went on a “date” with Sam, the all-star athlete performed by Mary Kate Olsen. As expected, the middle-school date was very awkward and child-like in the best way.

Greg discussed science and the weather with Sam, and how much he liked to play video games. A pleasant and unproblematic ‘love’ interest that Mary Kate and Ashley fans stan.

3 Trey Lipton – New York Minute (2004)

Jared Padalecki’s (known for his later role as Sam Winchester) puppy-dog eyes are so hard to ignore, and he was ever the supportive boyfriend to Ashley’s fiery Roxy in New York Minute. It’s worth noting that both the boys in this movie were the last boyfriends that the twins ever had in a movie together.

Trey was the son of a Senator but had no airs about him. He loved his little dog a lot, and overall, he participated wholeheartedly in the antics of the twins in New York, which meant that he was a great sport too.

2 Michel – Passport To Paris (1999)

In one of the best Mary Kate and Ashley travel movies, the legendary Gregory Peck’s grandson Ethan Peck played Michel, the all-black wearing, surprisingly mature French teenager in Passport To Paris. He wore turtlenecks, showed Mary Kate’s Melanie around on a moped, fed her baguettes, and gave her a true tour de Paris.

The charm, his eagerness to take Melanie out, and his fantastic sartorial tastes (at least for a fourteen-year-old) makes him one of the most memorable boys in the Mary Kate and Ashley universe.

1 Griffin Grayson – Holiday In The Sun (2001)

No love interest can beat Griffin. He was the perfect choice, even when Madison (Mary Kate) was actually pining over Scott. He put his feelings aside selflessly, and became Cyrano to silly Scott who couldn’t woo Madison if his life depended on it.

His devotion to his unrequited love was immense, and he even called her his hobby, which was a lot sweeter than it sounds out of context. He wanted Melanie to be happy at the cost of his own happiness, so Austin Nichols’ Griffin is a great boyfriend, especially for Madison.

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