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18 TV Friends Who Dated the Same Person

TV Characters Who Dated the Same Person

18 TV Friends Who Dated the Same Person

TV Characters Who Dated the Same Person
Image Source: Everett Collection

Much like celebrity friends who have romanced the same person, there are a handful of TV characters who have also swam around in the same dating pool. From '90s love triangles like that of Brenda Walsh, Kelly Taylor, and Dylan McKay right on up to the crossover couples on recent seasons of Girls, we've rounded up the small-screen friends that broke "the code" — and somehow lasted through it. When you're done, be sure to check out the TV pals that kept things purely platonic and all the onscreen couples who found true love IRL.

1 Brenda Walsh and Kelly Taylor both date . . .

Brenda Walsh and Kelly Taylor both date . . .
Image Source: Everett Collection
1 / 38

. . . Dylan McKay!

. . . Dylan McKay!
Image Source: Everett Collection

Brenda (Shannen Doherty) and Kelly (Jennie Garth) both have their time in the sun with bad boy Dylan (Luke Perry) on Beverly Hills, 90210. Brenda and Dylan date first, but he and Kelly strike up a fling while Brenda is on vacation in Paris during the Summer — hey, it happens. Kelly and Dylan start dating, which obviously angers Brenda; their friendship takes a hit, but they eventually reconcile during the show's third season.

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2 Dylan McKay and Brandon Walsh both date . . .

Dylan McKay and Brandon Walsh both date . . .
Image Source: Everett Collection
3 / 38

. . . Kelly Taylor!

. . . Kelly Taylor!
Image Source: Everett Collection

Yes, Kelly dates her best friend's boyfriend as well as her best friend's brother — only on TV, right? Kelly and Brandon (Jason Priestley) enter into a relationship, and in season five, she has to pick between him and Dylan, who obviously is still in love with her. She picks Brandon, and they get thisclose to getting married, but he leaves town (and the show) for good.

4 / 38

3 Pacey Witter and Dawson Leery both date . . .

Pacey Witter and Dawson Leery both date . . .
Image Source: Everett Collection
5 / 38

. . . Joey Potter!

. . . Joey Potter!
Image Source: Everett Collection

When we first meet Joey (Katie Holmes) on Dawson's Creek, she is hopelessly in love with her childhood friend Dawson (James Van Der Beek). They begin dating in the show's second season, but things soon blow up after Joey cheats on Dawson with Jack (Kerr Smith), who ends up realizing that he's gay. Typical.

Cut to season three, and Joey begins a secret relationship with Dawson's best friend, Pacey (Joshua Jackson). There's a lot of dramatic back and forth between the trio throughout the rest of the series, but Joey and Pacey end up together, living in NYC — while Dawson finally gets to meet his idol, Steven Spielberg.


6 / 38

4 Barney Stinson and Ted Mosby both date . . .

Barney Stinson and Ted Mosby both date . . .
Image Source: CBS
7 / 38

. . . Robin Scherbatsky!

. . . Robin Scherbatsky!
Image Source: CBS

On How I Met Your Mother, friends Barney (Neil Patrick Harris) and Ted (Josh Radnor) both fall for their mutual pal Robin (Cobie Smulders); she and Ted date briefly in the beginning of the series before deciding that they're better off as friends, and she begins dating womanizer Barney in season four.

Robin and Barney end up getting married (though it doesn't last), and Robin ends up with Ted after his own wife passes away.

8 / 38

5 Carrie and Fred both date . . .

Carrie and Fred both date . . .
Image Source: IFC Films
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. . . Alexandra!

. . . Alexandra!
Image Source: IFC Films

During season three of Portlandia, both Fred (Fred Armisen) and Carrie (Carrie Brownstein) date their new roommate, Alexandra (played by Chloë Sevigny). The craziest part is that both characters are seeing Alexandra at the same time, and only find out when they finally compare notes. Alas, Alexandra cheats on — and then breaks up with — both of them.

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6 Finn Hudson and Noah "Puck" Puckerman both date . . .

Finn Hudson and Noah "Puck" Puckerman both date . . .
Image Source: Everett Collection
11 / 38

. . . Quinn Fabray!

. . . Quinn Fabray!
Image Source: Everett Collection

If you recall, Quinn (Dianna Agron) is dating Finn (Cory Monteith) in Glee's first season. She ends up cheating on him with his teammate and best friend Noah "Puck" Puckerman (Mark Salling) — and gets pregnant. Quinn and Puck's baby is born in the season one finale. She and Finn get back together after she cheats on Sam Evans (Chord Overstreet) with him.

12 / 38

7 Rachel Berry and Quinn Fabray both date . . .

Rachel Berry and Quinn Fabray both date . . .
Image Source: Fox
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. . . Finn Hudson!

. . . Finn Hudson!
Image Source: Everett Collection

While they don't exactly start out as pals, Glee's Rachel (Lea Michele) and Quinn form a friendship in season two; Rachel begins dating Finn after he breaks up with Quinn, and their on-and-off relationship lasts throughout the series, up until Finn (and Monteith's) tragic death during season five.

14 / 38

8 Ross Geller and Joey Tribbiani both date . . .

Ross Geller and Joey Tribbiani both date . . .
Image Source: Everett Collection
15 / 38

. . . Rachel Green!

. . . Rachel Green!
Image Source: Everett Collection

Ross (David Schwimmer) and Rachel (Jennifer Aniston) eventually end up together at the end of Friends, but we can't forget about that truly unnecessary romance she strikes up with Ross's best friend, Joey (Matt LeBlanc), during the show's eighth season. Why does that even happen?

16 / 38

9 Jane Lane and Daria Morgendorffer both date . . .

Jane Lane and Daria Morgendorffer both date . . .
Image Source: Everett Collection
17 / 38

. . . Tom Sloane!

. . . Tom Sloane!
Image Source: MTV

Yup, even Daria and Jane fall for the same guy. In Daria's third season, Jane and Tom meet and begin dating. Daria, feeling threatened by the fact that Tom has essentially taken away her only friend, ends up hating him — until, after spending more time together, she realizes just how much they have in common.

Jane and Tom eventually split up, and Jane admits that he and Daria are better suited for each other. Soon after, Daria and Tom officially become a couple. While it doesn't work out, they do resolve to stay friends.

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10 Kelso, Hyde, and Fez all date . . .

Kelso, Hyde, and Fez all date . . .
Image Source: Everett Collection
19 / 38

. . . Jackie Burkhart!

. . . Jackie Burkhart!
Image Source: Everett Collection

On That '70s Show, Jackie (Mila Kunis) first dates Kelso (Ashton Kutcher). After a series of breakups and makeups, they split for good and Jackie is soon romanced by Hyde (Danny Masterson). By the end of the series, Jackie realizes that Fez (Wilmer Valderrama) is the guy for her, and they begin dating and ultimately get married.

Though she may have dated all three of the friends on screen, it was Ashton Kutcher who got the girl IRL, as he and Mila got married in 2015 and are parents to daughter Wyatt.

20 / 38

11 Caroline and Elena both date . . .

Caroline and Elena both date . . .
Image Source: The CW
21 / 38

. . . Stefan!

. . . Stefan!
Image Source: The CW

Elena (Nina Dobrev) and Stefan (Paul Wesley) date on and off until season four of The Vampire Diaries, when she breaks up with him to be with Damon (Ian Somerhalder). Elena's BFF Caroline (Candice Accola) begins a relationship with him in season six that also drops off and picks up.

22 / 38

12 Damon and Stefan both date . . .

Damon and Stefan both date . . .
Image Source: The CW
23 / 38

. . . Katherine!

. . . Katherine!
Image Source: The CW

Elena's doppelgänger, Katherine, romances both brothers at the same time — and for the record, so does Elena.

24 / 38

13 Piper Chapman and Polly Harper both date . . .

Piper Chapman and Polly Harper both date . . .
Image Source: Netflix
25 / 38

. . . Larry Bloom!

. . . Larry Bloom!
Image Source: Netflix

On Orange Is the New Black, Larry (Jason Biggs) and Piper (Taylor Schilling) are engaged when she first enters Litchfield prison. On the inside, Piper rekindles her relationship with ex-girlfriend Alex (Laura Prepon) while Larry begins getting closer to Piper's best friend, Polly (Maria Dizzia), who has recently had a baby. Polly and Larry begin an affair, which causes Polly to break up with her husband and Larry to break up with Piper.

26 / 38

14 Jessa Johansson and Hannah Horvath both date . . .

Jessa Johansson and Hannah Horvath both date . . .
Image Source: HBO
27 / 38

. . . Adam Sackler!

. . . Adam Sackler!
Image Source: HBO

Girls' first four seasons center around Hannah (Lena Dunham) and Adam (Adam Driver)'s on-again, off-again romance, but by season five, the actor begins pursuing one of Hannah's best friends, Jessa (Jemima Kirke). Hannah eventually finds out . . . and isn't happy.

28 / 38

15 Shoshanna Shapiro and Marnie Michaels both date . . .

Shoshanna Shapiro and Marnie Michaels both date . . .
Image Source: HBO
29 / 38

. . . Ray Ploshansky!

. . . Ray Ploshansky!
Image Source: HBO

Ray (Alex Karpovsky) dates Shoshanna (Zosia Mamet) during Girls' second season, but things come to a sad end after Shosh breaks up with him because of his negative attitude and lack of ambition.

In season three, Ray strikes up a fling with Marnie (Allison Williams) — who, coincidentally, is the ex-girlfriend of his friend Charlie (Christopher Abbott). Ray carries a torch for Marnie throughout her relationship and short-lived marriage in season five, and also manages to become friends with Shosh again.

30 / 38

16 Olivia Pope and Mellie Grant both date . . .

Olivia Pope and Mellie Grant both date . . .
Image Source: ABC
31 / 38

. . . Fitzgerald Grant!

. . . Fitzgerald Grant!
Image Source: ABC

Ah, Scandal. It goes without saying that Mellie (Bellamy Young) and Olivia (Kerry Washington) don't start out as friends — after all, Olivia is sleeping with Mellie's husband, who also happens to be the president of the United States — but through some straight-up soap opera sorcery, the first lady decides that Fitz and Olivia's affair actually makes her life easier.

By the show's fifth season, Olivia and Fitz are no longer, and Mellie and Olivia have teamed up for her presidential campaign — a friendship they seal with a night of girl talk and moonshine.

32 / 38

17 Vanessa Abrams and Jenny Humphrey both date . . .

Vanessa Abrams and Jenny Humphrey both date . . .
Image Source: Everett Collection
33 / 38

. . . Nate Archibald!

. . . Nate Archibald!
Image Source: Everett Collection

Nate (Chace Crawford) and Vanessa (Jessica Szohr) date briefly, off and on, during the first two seasons of Gossip Girl. During season two, Nate begins dating Jenny (Taylor Momsen), who keeps their romance a secret so that Vanessa — who is like a sister to her — doesn't find out. Spoiler alert: Vanessa finds out.

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18 Serena van der Woodsen and Blair Waldorf both date . . .

Serena van der Woodsen and Blair Waldorf both date . . .
Image Source: Everett Collection
35 / 38

. . . Nate Archibald . . .

. . . Nate Archibald . . .
Image Source: Everett Collection

Nate (Chace Crawford) first dates his childhood friend Blair (Leighton Meester) before moving on to strike up a relationship with Serena (Blake Lively).

36 / 38

. . . Carter Baizen . . .

. . . Carter Baizen . . .
Image Source: The CW

Carter (Sebastian Stan) starts dating Blair during season two of Gossip Girl — Leighton Meester and Sebastian Stan also carried on a real-life romance for a couple of years. In season three, Carter cut Blair loose and began dating Serena.

37 / 38

. . . and Dan Humphrey!

. . . and Dan Humphrey!
Image Source: Everett Collection

Dan (Penn Badgley) and Serena begin dating in Gossip Girl's pilot episode and continue on and off throughout the series, ultimately tying the knot. It is during one of their "off" phases that Dan and Blair become more than just friends, in season four. Oh, and Penn Badgley and Blake Lively also dated off screen for three years.

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