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  3. Pretty Little Liars: Ranking the romances of Rosewood

Pretty Little Liars: Ranking the romances of Rosewood

By Samantha Highfill,  Isabella Biedenharn and Breanne L. Heldman Updated September 28, 2022 at 01:57 AM EDT
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Ranking the Rosewood romances

PLL3way
Credit: Eike Schroter/ABC Family/Getty Images; Adam Taylor/ABC Family/Getty Images; Eric McCandless/ABC Family/Getty Images

In honor of HBO Max's Pretty Little Liars spin-off series, Pretty Little Liars: Original Sin, we're ranking 20 of the original show's most memorable romantic pairings.

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20. Jason and CeCe

ABC Family's "Pretty Dirty Secrets"
Credit: Adam Rose/ABC Family via Getty Images

Accidentally dating your sibling is a pretty little plotline we'd rather forget.

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19. Toby and Jenna

KEEGAN ALLEN, TAMMIN SURSOK
Credit: Randy Holmes/Freeform

Since they weren't blood-related — and Toby (Keegan Allen) was blackmailed — this stepsibling pairing isn't exactly incest…but it still triggers our gag reflex.

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18. Alison and Elliott Rollins

Freeform's "Pretty Little Liars" - Season Six
Credit: Eric McCandless/Freeform via Getty Images

If a relationship is all about trust and communication, then this one straight-up fails. Rollins (Huw Collins) lies to Ali (Sasha Pieterse) about his name, his past, and pretty much everything else. Also, remember when he put her in that Hannibal Lecter mask? That's not what we'd call "romantic."

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17. Emily and Ben

Emily-and-Ben
Credit: Freeform

Emily's (Shay Mitchell) boyfriend at the start of the series wasn't just a bad match because she wasn't interested in men, he also tried to sexually assault her in the girls' locker room — and that's a bad look on anyone, regardless of gender. Yikes.

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16. Emily and Sabrina

emily-and-sabrina2
Credit: Freeform

Emily takes all of her relationships very, very seriously, but we couldn't do the same for her dalliance with the Brew's crunchy baker.

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15. Ashley Marin and Detective Wilden

Ashley-Marin-and-Wilden
Credit: Freeform

A relationship built on bribery isn't one we can root for.

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14. Hanna and Jordan

Freeform's "Pretty Little Liars" - Season Six
Credit: Eric McCandless/Freeform via Getty Images

Jordan (David Coussins) should get some credit here: He seemed like a decent guy, a kind fiancé to Hanna (Ashley Benson), and…he was rich! But compared to her true love, Caleb (Tyler Blackburn), Jordan was just a slice of white bread that went stale too soon.

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13. Paige and Emily 

SHAY MITCHELL, LINDSEY SHAW
Credit: Adam Taylor/Freeform

Don't they look so cute and in love? Well, they really shouldn't be, because the first rule of dating is: Don't date someone who has tried to MURDER YOU.

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12. Toby and Yvonne

Toby-and-Yvonne
Credit: Freeform

Toby might be the unluckiest character of all on this series, and Yvonne (Kara Royster) became some unfortunate collateral damage. The pair seemed happily in love (despite Toby's always-lingering feelings for Troian Bellisario's Spencer) when we first met the politician's daughter, but their ill-fated car wreck proved they weren't exactly going to get the ever-after they'd imagined. While they managed to tie the knot after Yvonne awoke from her coma, she died moments later. #TearsforToby.

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11. Emily and Alison

SHAY MITCHELL, SASHA PIETERSE
Credit: Eric McCandless/Freeform

Sorry, shippers: As nice as it would be to have Emison really be #endgame, it's difficult to get on board with this duo when everything about their sometimes-romance feels like it's just manipulation on Ali's part and a heartbreaking, unrequited crush for Emily.

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10. Aria and Jason

ABC's "Pretty Little Liars" - Season Two
Credit: Eric McCandless/ABC Family via Getty Images

In the space of the five-year time jump, Ali's big bro (Drew Van Acker) and Aria spent some quality time together, and it was en fuego! And, let's be honest, there was some chemistry between them long before that. Plus, seeing Jason put his heart on the line when he made a plea for Aria (Lucy Hale) in season 7 had us a little weak in the knees.

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9. Spencer and Wren

ABC Family's "Pretty Little Liars" - Season Three
Credit: ERIC MCCANDLESS/ABC Family via Getty Images

Honestly, Spencer has chemistry with everyone, but, to be fair: Wren (Julian Morris) came first. Sure, he was engaged to Spencer's sister, but the secrecy of it all made it even hotter. Also, he has that adorable accent.

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8. Mike and Mona

Mike and Mona
Credit: Freeform

Say what you want about these two, who have both toed the line between good and evil, but their relationship made sense in a strange sort of way — and we'll never forget how devastated Mike (Cody Christian) was when Mona (Janel Parrish) "died."

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7. Spencer and Marco

Freeform's Pretty Little Liars - Season Seven
Credit: Eric McCandless/Freeform via Getty Images

Did you see that elevator scene?! Between that and the fact that Marco (Nicholas Gonzalez) actually seems like a good cop — a real rarity in Rosewood — Spencer has multiple solid options, if you really think about it.

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6. Aria and Jake

ABC Family's Pretty Little Liars - Season 4
Credit: Ron Tom/ABC Family via Getty Images

When Aria stepped outside her normal circle and started hitting the mats with her smoke-show karate teacher Jake (Ryan Guzman) in season 4, we started playing a den-den daiko like Mr. Miyagi to cheer them on.

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5. Spencer and Caleb

Freeform's Pretty Little Liars - Season Seven
Credit: Ron Tom/Freeform via Getty Images

It's not often that a series can switch characters from two of its beloved relationships — Haleb and Spoby — and somehow make it work, but the chemistry between Spencer and Caleb made this pairing seem like a viable alternative (with which many fans fell in love).

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4. Maya and Emily

ABC's "Pretty Little Liars" - Season Two
Credit: Randy Holmes/ABC Family via Getty Images

Every relationship Emily has been in for the rest of the series (looking at you, Paige) pales in comparison to her passionate and tragic early romance with Maya St. Germain (Bianca Lawson) — the beautiful, confident girl who helped her come out of the closet.

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3. Spencer and Toby

KEEGAN ALLEN, TROIAN BELLISARIO
Credit: Adam Rose/ Freeform

After so many years of love and pining, he built a house for her, you guys! He's basically Ryan Gosling's Noah in The Notebook! Even though one of them was engaged to someone else, Spoby will always be endgame, as proven in the series finale.

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2. Ezra and Aria

LUCY HALE, IAN HARDING
Credit: Eric McCandless/Freeform

Yes, this relationship began when Aria was underage. And yes, there was that whole book debacle. But — for fictional purposes of this show — none of that matters when you find your soulmate, and Aria and Ezra (Ian Harding) have been the romance that's lasted through it all. (Seriously. They hooked up in the pilot, which makes them the OG ship, as problematic as it may be.)

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1. Hanna and Caleb

ASHLEY BENSON, TYLER BLACKBURN
Credit: Adam Taylor/Freeform

Sure, Caleb's post-college romance with Spencer (and Hanna's engagement to Jordan) may have threatened this long-lasting pair, but nothing could keep our favorite fashionista-tech genius duo apart for long. Hey, they even survived Caleb's jaunt over to Ravenswood for that short-lived spin-off! Hanna and Caleb respect each other, work together, and just fit — plus, her mom loves him, which is always a good thing.

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    1 of 21 Ranking the Rosewood romances
    2 of 21 20. Jason and CeCe
    3 of 21 19. Toby and Jenna
    4 of 21 18. Alison and Elliott Rollins
    5 of 21 17. Emily and Ben
    6 of 21 16. Emily and Sabrina
    7 of 21 15. Ashley Marin and Detective Wilden
    8 of 21 14. Hanna and Jordan
    9 of 21 13. Paige and Emily 
    10 of 21 12. Toby and Yvonne
    11 of 21 11. Emily and Alison
    12 of 21 10. Aria and Jason
    13 of 21 9. Spencer and Wren
    14 of 21 8. Mike and Mona
    15 of 21 7. Spencer and Marco
    16 of 21 6. Aria and Jake
    17 of 21 5. Spencer and Caleb
    18 of 21 4. Maya and Emily
    19 of 21 3. Spencer and Toby
    20 of 21 2. Ezra and Aria
    21 of 21 1. Hanna and Caleb

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