It’s time to turn our attention to our favorite set of twins. No, it’s not Lindsay and Linsday 2.0 in The Parent Trap. It’s also not Dylan and Smoking Guy Sprouse. It’s the Olsen twins!!!
The original dynamic duo, the Meryl Streeps of their generation, the style icons, Mary Kate and Ashley Olson are the Millennial It girls. It doesn’t matter that I still can’t tell them apart, because they are both amazing, and together they’re even better.
But rather than talk about their best performances, we’re going to intentionally fail the Bechdel Test and rank all of their best on-screen boyfriends. So get your infinity scarves out and prepare for the ultimate blast to the past, let’s do this from worst to best.
Jean and Michel — A Passport to Paris
I am going to package these two as one, because I literally cannot tell them apart. They have no discerning qualities. Their character description is just “French boys who flirt.”
Our girlies, Mel (Mary Kate) and Ally (Ashley) are in Paris visiting their grandfather who is the American ambassador. He seems LOADED! They want to go and have fun, I mean they’re thirteen!!! Basically an adult, RIGHT?
So they go shopping with a supermodel, meet these cuties and get into trouble with them. These are bad boys who get them on the wrong side of the law, so I’m relegating them to the bottom of the list. Also I don’t think they can speak English so the options are limited at thirteen.
Marcus — The Challenge
So for The Challenge, imagine if the Olson twins were on a season of Survivor or I’m a Celebrity, Get Me Out of Here… That’s the vibe we’re going for.
The estranged twins are complete opposites, and both manage to get onto a competition show to win a scholarship. They’re put on the same team, as somehow Marcus (the intern) realizes they hate each other. Okay, someone is good at Google!
They’re battling each other as much as the other team, and Marcus is trying to get good info on the girlies for his boss. Somehow the boss is the villain even though he is giving out a bunch of scholarships??
Marcus is super cute, but I can’t negate the fact that he is SPYING on Lizzie (Ashley). He gets their worst fears (heights and snakes) and tells his boss so they can be included in a challenge. Not cool dude!! I know he’s sorry in the end and they make up for it, but I’m still mad.
Also, he’s an intern at this big production company, which makes me think he’s a few years older than this high school student…
Ryan — When in Rome
Okay, now our girlies felt like visiting Italy so their next film is set in Rome. They’re here for an internship in fashion or so, and they’re failing at adulting.
Ryan is a bad boy and I just can’t resist those. He’s the nephew of Derek Hammond, who owns the fashion company these girls are apparently interning at. So Ryan doesn’t do much wrong really and he even surfs, but he does distract Laila (Ashley) from her photography and bigger career goals. Also, he gels up his hair into spikes and it gives me the ick.
At the end, he wants to kiss Laila and she says no. Love the consent, and love that she pied him.
Paolo — When in Rome
Never trust an Italian named Paolo, I learned this from The Lizzie Maguire Movie. But this Paolo breaks tradition, as he’s actually a good guy I guess?
The girlies are in Rome for an internship, along with four others (including Paolo) and it’s totally fashion-related. Paolo starts hitting it off with Charli (Mary Kate) and there are cute montages, like moped rides, exploring sights, and longing gazes. It’s all very wholesome.
Then at the end, we get a big smooch, which is always a pleasant surprise in these films!!
Jim — New York Minute
Okay, having the name Jim already starts him a little lower on the ladder. But my main issue with this love interest is how seemingly pointless he is to the plot. New York Minute is about Jane (Ashley) trying to give a speech to get into Oxford or Cambridge or another stuffy British school, and Roxie (Mary Kate) trying to get her demo to Simple Plan. Lol.
Jim’s main purpose is to be the reason they’re in trouble in the first place, as Jane is flirting with him when the illegal piracy microchip is accidentally slipped into their bag in the first place. Then we see him every time he crashes into Jane as a bike messenger. He needs to learn to bike better. He could seriously injure someone. We assume he ends up with Jane as he’s in the final scene, but we don’t get much more. Bland.
Adam — The Challenge
Okay, he’s not as bad as the traitor, Marcus, but let’s not forget that Adam plays for the other team! No, the literal other team: The Mayans. He is Shane’s (Mary Kate) competition for the scholarship.
He’s also a total jock with little personality, which doesn’t bode in his favor. BUT the two bond over having divorced parents, which is really cute and sensitive. And despite being against her, he plays fair and seems really into her. They get disqualified from a round for kissing, and idk maybe it was worth it?
Jordan — Holiday in the Sun
The girls are SO MAD because they can’t go to Hawaii with their friends and instead have to go to an all-inclusive resort in the Bahamas with their parents, ugh! Where they get to lounge around all day and barely hang out with those parents, ugh! Isn’t life the worst??
Well, naturally our girls get embroiled in a detective plot, as Jordan the hot aquarium worker (wow phrase I never thought I’d use) gets falsely accused of stealing antiques. The girls have to prove his innocence to keep him out of jail, especially as Alex (Ashley) has a big crush on him.
Despite being the source of their trouble, Jordan gets extra points as wealthy heiress Brianna (played by THE Megan Fox) is also into him. If she wants him, he must be hot!!
Obviously, he ends up being innocent and it’s all part of some bigger conspiracy. Yay fun in the sun!
Griffen — Holiday in the Sun
Now I’m a little biased with this one, as Griffen’s storyline involves one of my favorite things: a Cyrano-esque plotline! Basically, he is helping Scott, to win over his friend/crush, Maddison (Mary Kate) by telling him what to say. But really she is falling for him. Just think of She’s the Man for another example.
While I don’t like Griffen’s sneakiness in doing this, I love a good friends-to-lovers arc and whenever this miscommunication trope is used, so he gets a better score than Jordan for this film.
Larry — So Little Time
Third place goes to the blueprint for friends to lovers, Larry in So Little Time. I am very aware that this isn’t actually a film, but rather their series. I had this entire show on DVD and used to watch it religiously after school. I was obsessed with the twins, and I pined for Larry and Riley (played by Mary Kate) to just get together.
I’ll admit he was kinda dorky, but he gave me Logan in Veronica Mars energy, if Logan wasn’t such a bad boy. Everyone but Riley knew that he was into her, and he’d do anything to get her attention each episode, including stealing charity money to buy her concert tickets. Maybe he is a bit of a bad boy…
I was so relieved when they finally kissed, even though Riley then vehemently denied it. Then she got super jealous when he got together with Cammi. I think if the show hadn’t been rudely canceled, we would’ve seen these two finally get together.
Brian — Winning London
This masterpiece of a film is described as “Olsen twins head to international competition, pursue boys.”
I couldn’t put it better myself! Chloe (Mary Kate) is off to London for Model UN, and her sister Riley (Ashley) joins to fill the last slot. Riley also has another ultimatum of trying to win the heart of Brian, another member of the team.
Brian is nerdy cute, and he wins my heart quickly as well. The highlight was when the two of them kissed in the air vents heeheee!
Trey — New York Minute
What’s not to like about Trey? He’s rich, charismatic, and down to help the twins escape an elaborate piracy conspiracy (the irony is that I streamed this film).
Well, I’ll tell you what’s not to like: HIS CRUSTY WHITE DOG. Reinaldo (who names a dog that?) looks like he has been reanimated from the dead, and becomes key to the plot when he swallows a chipcard. When the dog got yeeted out the window, I almost hoped we were free of him.
But back to Trey. He’s a definite cutie and has eyes for Roxie (played by Mary Kate) throughout. In a twist on the regular damsel in distress, he gets kidnapped and held in a trunk, and Roxie must save him.
In the finale, we see him watching Roxie’s band in a recording studio, so we can assume he is supportive of her career – yay!
James — Winning London
DING DING DING – WE HAVE A WINNER!!! I present to you Lord James of Somewhere in England, the rightful winner of the crown of Olson.
Why is James such a babe? Well, his daddy is an earl who puts looooads of pressure on him, which is super tough to deal with. But James stays true to who he is and skives to hang out with our girlies.
He teaches them all about the UK, which is apparently tea, fencing and polo. Of course. He’s gorgeous and the accent wins my heart, as it did Chloe’s (Mary Kate).
Just like Taylor Swift, I can’t resist a London Boy.