Movie Romance
15 of Mary-Kate & Ashley Olsen’s Movie Boyfriends, Ranked
Mary-Kate Olsen and Ashley Olsen will celebrate their 39th birthdays on June 13, and while they’re crushing it in the fashion industry these days, it’s been more than 20 years since we’ve seen them in a film together.
The Olsen twins stopped making movies together after 2004’s New York Minute. Although Mary-Kate has had a few film and television credits since then, the sisters have mostly retreated from the spotlight and are instead focused on building their fashion empire.
But us millennials will never forget the chokehold the Olsen twins had on us in the 1990s and early 2000s. They were everywhere. I know I had an entire drawer dedicated to VHS tapes from their movie collection, with films including Billboard Dad, Passport to Paris, Holiday in the Sun, and plenty more.
As the girls got older, they started having love interests in their movies, and we’re looking back at the best of them … and the worst. Scroll down for our ranking of Mary-Kate and Ashley’s movie boyfriends, and let us know in the comments section if you agree with our decisions!
15. Jean, Passport to Paris
The language barrier is partly to blame here, but this guy was kind of a dud. Allyson (Ashley) getting her first kiss with Jean (Brocker Way) at the end of the movie was a nice touch, but there wasn’t much substance here.
14. Jordan, Holiday in the Sun
Alex (Ashley) and Jordan (Ben Easter) had the ultimate beach romance after they met in the Bahamas while she was a guest at the resort he worked at. But not everything about their time together was romantic. I mean, petting stingrays and making fish smoothies? Gross. There were some perks, like the fact that Jordan had access to a boat and knew all the best spots, but he also unintentionally ended up getting the group arrested. It’s a no for me.
13. Marcus, The Challenge
Marcus (Brian Skala) may have come to his senses and told off his boss who wanted to pit his love interest, Lizzie (Ashley), and her estranged sister, Shane (Mary-Kate), against each other, but that doesn’t change the fact that he was the one who came up with the idea to cast them on the same reality competition show after their falling out. He spent the first several days of his relationship with Lizzie lying about his involvement in the scheme. Marcus may be charming and cute, but he cannot be trusted! Oh, and then love-bombing Lizzie after just a few days of knowing each other? Nope.
12. Brian, Winning London
Brian (Brandon Tyler) didn’t realize what was standing right in front of him — that would be Riley (Ashley), who’s had a crush on him for years. She even joined the debate team to spend time with him, but no matter how forward she was, something always kept getting in the way, and Brian didn’t work hard enough to get the girl. He did get her in the end, but it was a pretty pathetic showing. But props to him for eventually realizing it, I guess?
11. Sam, Getting There
Poor Sam (Talon Ellithorpe), he got totally friend-zoned by Kylie (Mary-Kate). There wasn’t much context to this relationship, so it’s hard to judge, but I’m not sure why she was so put off by him. The “snowboard bro” persona wasn’t exactly charming, but I kind of wish Kylie gave Sam a shot!
10. Griffen, Holiday in the Sun
Griffen (Austin Nichols) had a crush on Madison (Mary-Kate) for years, and their families’ trip to the Bahamas was the perfect place for him to put it in action. Unfortunately, her interest in Scott (Billy Aaron Brown) briefly got in the way, and Griffen proved he knew Madison better than anyone when he gave Scott pointers for winning her over. His undying devotion was cute … until it got creepy when he told Madison, “Everybody has a hobby, right? Let’s just say you’re mine.” But…she seemed to be into it?
9. Ryan, When in Rome
Leila (Ashley) formed a bond with her boss’ bad boy nephew Ryan (Derek Lee Nixon) in Rome, and I’m not really sure why she wasn’t willing to take things to the next level. Leila was convinced that Ryan was “spoiled, obnoxious, [and] kind of arrogant,” but he didn’t come off as that bad to me!
8. Averey, Our Lips Are Sealed
The twins’ love interests in Our Lips Are Sealed were the surfer boys who didn’t fit in with the cool crowd and didn’t care. The guys were so similar. They both had carefree attitudes and showed the girls how to have fun instead of stressing out about being popular. Abby’s (Ashley) guy Averey (Scott Swalwell) just falls a little lower on the list because of his corny lines about how important surfing is (but, as she said, “I know, I know, but he’s so cute!”)
7. Pete, Our Lips Are Sealed
Maddie’s (Mary-Kate) beau in Our Lips Are Sealed was Pete (Ryan Clark). See above for the rest.
6. Michel, Passport to Paris
Melanie’s (Mary-Kate) Passport to Paris relationship was a lot more believable than her sister’s. Since Michel (Ethan Peck) spoke English, he was the group’s translator, and he was a lot more mature than his French friend Jean. It made me want to root for Melanie to get her first kiss much more than Allyson (and she did!)
5. Adam, The Challenge
Adam (Lukas Behnken) and Shane (Mary-Kate) connected from the get-go when they were both contestants on a reality competition show, and their relationship flourished from there. Although there were some cheesy moments, this romance actually felt like it progressed in a normal way compared to others in the MKA universe, and with Adam going to school at Stanford (not far from Shane’s home in Los Angeles), there was potential for a real future too!
4. Paolo, When in Rome
The perfect example of opposites attract. At first, Charli (Mary-Kate), who described herself as “uptight,” wasn’t sure she’d be able to make it work with the “laidback” Italian Paolo (Michelangelo Tommaso), but their feelings for each other outweighed their differences. The city of Rome was the perfect backdrop for their romance, and Charli helped Paolo take their work seriously, while he made sure she let loose and have fun.
3. Trey, New York Minute
Even before Trey (Jared Padalecki) knew who Roxy (Mary-Kate) was, he was willing to cover for her when she snuck into his mom’s hotel room. He went out of his way to find her after they were separated and joined her on a trek through the city to save her sister’s day … no questions asked. Swooon!
2. James, Winning London
Hot, rich, British, son of a Lord who is nothing like his power-hungry father? Running out on the chance to win a debate competition just to get the girl? Yes, please! James (Jesse Spencer) and Chloe (Mary-Kate) may have been on opposing debate teams in Winning London, but that didn’t stop their love story from flourishing. They matched each other intellectually and emotionally, making them a perfect match. In fact, it was Chloe’s competitiveness that almost came between them. James was nothing but the perfect gentleman, and he proved time and time again that he was willing to do whatever it took to make it work.
1. Jim, New York Minute
Back-to-back meet cutes? ADORABLE! Jim (Riley Smith) was probably not the type of guy Jane (Ashley) would normally date, but from the moment they bumped into each other (literally) their chemistry was obvious. Oh, and he transferred schools to move to London for her? SO MUCH YES. Marry that man, Jane!
