7 Iconic Love Triangles That Really Had Us Wondering Which Ship Was the Best

Iconic love triangles! Teen dramas and romance movies have this secret sauce that make them as compelling and addictive as they are. It's one thing when you take an attractive couple and mix it with a meet-cute or exciting backstory, the sum of the parts of which is a picture-perfect rom-com, whether on TV or in the movies. But then, on top of that, if you throw in a juicy love triangle, these love stories become even more alluring.

Love triangles have been a part of the equation for years and while they were really on the rise in the late 1990s and early 2000s, they remain a beloved part of the formula and still have fans divided on who the best ship (a shortened version of relationship) is.

From Dawson’s Creek and Sex and the City to The Summer I Turned Pretty, there is an ever-present need for these thrilling iconic love triangles and choosing sides.

1. Dawson’s Creek (1998)

CHARACTER IN THE MIDDLE: Joey Potter (Katie Holmes)

OPTION 1: Dawson Leery (James Van Der Beek

Strengths: Joey’s Best Friend; sweet and caring

Weaknesses: Didn’t want Joey to grow up and move on; felt ownership over her

OPTION 2: Pacey Witter (Joshua Jackson)

Strengths: Lets Joey make her own decisions; loved Joey rather than the idea of her

Weaknesses: Emotionally unavailable and sometimes immature

BACKGROUND: This love triangle runs deep for a lot of fans of the 1998 drama series. When the show started, it seemed there was no better potential pairing than lifelong best friends and love interests Joey and Dawson. When they finally kiss in the first season finale, fans were thrilled. But throw Dawson’s other best friend, Pacey, into the mix and that’s when the real drama starts. Joey and Pacey fall for each other unexpectedly, which did not bode well for Dawson and Joey’s future.

HOW IT ENDS: As everyone knows, Pacey and Joey wound up together in the finale, much to the delight of many viewers.

HOW IT SHOULD HAVE ENDED: While there were positives and negatives to both characters, Joey and Pacey made the most sense based on the storyline and how they grew together. Similar to viewers, Jackson fought for his character to end up with Holmes’ character. “I am the advocate! I was like, 'Hell no! No. No. No. That's [Dawson and Joey] not gonna work for me.’”

Van Der Beek agreed with Jackson, sharing, “[Joey and Pacey] felt right to me. It seemed like it made more sense.”

2. Gilmore Girls (2000): Iconic Love Triangles

CHARACTER IN THE MIDDLE: Rory (Alexis Bledel)

OPTION 1: Jess Mariano (Milo Ventimiglia)

Strengths: Attentive, bad-boy, similar interests to Rory

Weaknesses: Immature, a loner

OPTION 2: Dean Forester (Jared Padalecki)

Strengths: Sweet and caring

Weaknesses: Jealous, a Cheater (later on)

BACKGROUND: Yes, this is the ultimate TV debate: Jess, Dean, or Logan? But before that question sprang to life and deeply divided viewers, it was between Jess and Dean for high school Rory. When Jess rolled into Stars Hollow, Dean was pretty threatened of his connection with Rory. But she told him repeatedly, there was nothing going on between them. All that changed, however, when they kissed in the season 2 finale of Gilmore Girls and brought this debate to life.

HOW IT ENDS: Ultimately, Rory doesn’t end up with either of her loves, although she does date each of them for a significant period. Rory dated Dean from seasons 1-3 and again in season 5 when they rekindled (If you know, you know) and Jess throughout season 3, though he does come back quite a few times.

HOW IT SHOULD HAVE ENDED: Of course, Logan is eventually introduced into the mix of potential loves for Rory, but the Yale student should have ended up with Jess. Despite his immaturity in the early seasons, he showed a lot of growth when he reappeared in season 6, unlike Dean.

3. The Vampire Diaries (2009)

CHARACTER IN THE MIDDLE: Elena (Nina Dobrev)

OPTION 1: Stefan (Paul Wesley)

Strengths: Sweet, caring and loving

Weaknesses: He can be murderous

OPTION 2: Damon (Ian Somerhalder)

Strengths: Attractive, confident, in love with Elena

Weaknesses: Impulsive and sometimes a murderer

BACKGROUND: When you think of love triangles between a girl and two brothers, your mind probably instantly snaps back to 2009 when Elena was choosing between Stefan and Damon. Elena was back and forth between the brothers for the first four seasons, causing some major tension between the Salvatores and making real life pretty dull in comparison. But if you had the choice between a sweet but brooding vampire and a fun and confident one, you might have a hard time choosing, too.

HOW IT ENDS: Elena eventually ends up with Damon after some back and forth, multiple breakups and a magical coma. It was not without trials and tribulations, but the duo finally made it work in the end.

HOW IT SHOULD HAVE ENDED: Elena and Damon were the perfect ending. However, the show’s creator, Kevin Williamson, thought differently. “Well, I always thought it would be Stefan and Elena. They were sort of the anchor of the show.” But despite what everyone thought would happen, a majority of viewers were thrilled with this end.

4. The Summer I Turned Pretty (2022): Iconic Love Triangles

CHARACTER IN THE MIDDLE: Belly (Lola Tung)

OPTION 1: Conrad (Chris Briney)

Strengths: Belly’s longtime crush, attentive and thoughtful

Weaknesses: Emotionally unavailable

Option 2: Jeremiah (Gavin Casalegno)

Strengths: A good friend, caring towards Belly

Weaknesses: Jealous of Conrad

BACKGROUND: Speaking of brother love triangles, one of the most debated love triangles in the present is that of Belly, Conrad and Jeremiah. Based on the 2009 book of the same name, Belly is caught between her lifelong feelings for Conrad Fisher and her burgeoning feelings for his brother, Jeremiah.

HOW IT ENDS: The series hasn’t come to an end yet and therefore audiences don’t know who Belly ultimately chooses. At the end of season 1, she chose Conrad and at the end of season 2, she chose Jeremiah. The third book does have an answer, but we won’t spoil it.

HOW IT SHOULD END: Although it hasn’t ended yet, most fans are in favor of Belly and Conrad. Their undeniable chemistry is clear from the moment they lay eyes on each other in the first episode.

5. Beverly Hills, 90210 (1990)

CHARACTER IN THE MIDDLE: Dylan (Luke Perry)

OPTION 1: Brenda (Shannen Doherty)

Strengths: Driven and passionate

Weaknesses: Idealist and sometimes self-destructive

OPTION 2: Kelly (Jennie Garth)

Strengths: Compassion and ability to overcome challenges

Weaknesses: Self-centered

BACKGROUND: Brenda and Dylan were an item from the very beginning of the series and fans loved them. The bad boy falls for the good girl: it’s a juicy storyline and one that is still popular today. But when Dylan unexpectedly falls for her best friend (and cheats with her!), a new love match was formed on the show.

HOW IT ENDS: Once Brenda finds out about Dylan and Kelly, Dylan ultimately chooses to be with Kelly. Although the couple breaks up a few times throughout the series, they ultimately end up together in the series finale and it is revealed in the reboot series that they have a child together.

HOW IT SHOULD HAVE ENDED: While Dylan and Kelly are an integral part of the 90210 story, Brenda and Dylan might have had more of a connection. However, both couples were important to the storylines and made for an addicting watch.

6. Sex and the City (1998): Iconic Love Triangles

CHARACTER IN THE MIDDLE: Carrie (Sarah Jessica Parker)

OPTION 1: Mr. Big (Chris Noth)

Strengths: Charming and passionate

Weaknesses: Emotionally damaged

OPTION 2: Aidan (John Corbett)

Strengths: Communicative and stable

Weaknesses: Irritable with Carrie (and vice versa)

BACKGROUND: Carrie is immediately into Mr. Big when she meets him on the street, the two having a torrid relationship with a lot of back and forth. When Carrie later meets Aidan, she falls for him but ultimately ends up cheating with Mr. Big, who is married. The couple split, but it isn’t the end of the road for either duo.

HOW IT ENDS: The series concludes with Carrie choosing Mr. Big, with the couple marrying in the first film. They are even together in the reboot series, And Just Like That, but when Mr. Big unexpectedly dies, she eventually finds her way back to Aidan.

HOW IT SHOULD HAVE ENDED: Although Carrie and Mr. Big were pre-destined for each other, the couple was rather toxic and perhaps not the best choice. Either could have been best, but Aidan may have been the better option for Carrie in the end.

7. Lucas with Peyton or Brooke on One Tree Hill

CHARACTER IN THE MIDDLE: Lucas (Chad Michael Murray)

OPTION 1: Brooke (Sophia Bush)

Strengths: Attentive, sweet and confident

Weaknesses: Sometimes self-centered

OPTION 2: Peyton (Hilarie Burton)

Strengths: Kind, independent and strong

Weaknesses: Rebellious, headstrong and a bit angry

BACKGROUND: When Lucas became a part of the inner circle, he was immediately attracted to Peyton, who didn’t feel the same way and had a boyfriend. After she rejected him, he moved on to her best friend, Brooke, who was a good girlfriend for Lucas. But when he eventually cheats with Peyton, a lot of drama and chaos ensues for the triangle.

HOW IT ENDS: Lucas and Peyton eventually end up together after a lot of back and forth, and the couple getting married and having a baby. While this love triangle divided fans at first, it was clear they were meant to be by the end of the show.

HOW IT SHOULD HAVE ENDED: While Brooke and Lucas were good for each other at one time, it was clear that Lucas and Peyton had undeniable chemistry and were meant to be together. And Brooke, too, got what she deserved when she met her future husband, Julian.

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