TV’s Most Hopeless, Angst-Ridden Romantics


If you always secretly wished that The West Wing was a lot more soapy, then mark your calendars for Sunday night, when a new show called Political Animals premieres on USA. At the heart of this fun new series is the Hammond family, a political dynasty in the vein of the Kennedys, who are every bit as flawed and riddled by scandal. There’s also a clear homage to the Clintons happening here. Sigourney Weaver’s Elaine Barrish is basically Hillary Clinton with a much better stylist; meanwhile, Ciarán Hinds as two-term president and general good ol’ boy Bud Barrish is cut from the same cloth as Bill. As in real life, the on-screen relationship between this fictionalized version of the couple is hard to comprehend. Like Carla Gugino, who plays the family’s nemesis, journalist Susan Berg, we can’t help but wonder why a woman as strong as Elaine would put up with a cheating husband — but then, she’s far from the first TV character to let her heart rule over her head. Click through for a roundup of some of the most hopeless, angst-ridden romantics in recent television history.

Elaine Barrish in Political Animals The object of her obsession: Bud Hammond Classic quote: “I stayed because I loved him… [I left] because after 30 years, in that moment, exhausted from the campaign, I finally had the strength to.”

When we first meet former first lady Elaine Barrish Hammond, she’s campaigning for president and married to Bud Hammond, a womanizer who closely resembles Bill Clinton — charming in his public life, but a total philanderer in his private life. After failing to secure the Democratic party nomination, Elaine (who’s viewed as a cold opportunist by the public) decides that she wants a divorce that very night. The next time that we see her, Elaine is the Secretary of State, while Bud has become a bit washed up, trading on his celebrity to score dates with TV stars half his age. But here’s the rub: It’s obvious, at least in the pilot, that Elaine still has strong feelings for Bud, and he’s to ready to exploit the hold that he has over her to get back in the game. “All anybody ever talks about is your ambition,” he tells her. “They never talk about your heart — I don’t know why they don’t see it, ’cause it’s all I ever saw… That, and you were the foxiest piece of ass that I’d ever laid eyes on… still are.” With lines this smooth, it seems like if Elaine isn’t careful about separating her personal life from her political one, she’s doomed to repeat past mistakes.

Kevin Arnold in The Wonder Years The object of his obsession: Winnie Cooper The classic quote: “Once upon a time there was a girl I knew that lived across the street. Brown hair, brown eyes. When she smiled, I smiled. When she cried, I cried. Every single thing that happened to me that mattered, in some way, had to do with her. That day Winnie and I promised each other that no matter what, we’d always be together. It was a promise full of passion and truth and wisdom. It was the kind of promise that could only come from the hearts of the very young.”

Kevin and Winnie shared a lot of firsts — their first kiss, first slow dance, first make-out party, first time going all the way — and when he’s not with her, he’s desperately longing for her (let’s face it, as nice as they might be, Becky Slater and that townie from Lake Winnihacci just don’t stack up). Remember when Winnie’s family moved away and Kevin tried to give her that ring? Or when Winnie gave Kevin the ID bracelet, then he lost it? Sigh. After watching their relationship evolve over the course of six seasons, most of us expected that they’d end up together in the end, but in the series finale we discover that when Winnie returns from studying art history in Paris, Kevin is married with a kid. This, after they wrote each other a letter every week for eight whole years! Eight years!

Ally McBeal in Ally McBeal The object of her obsession: Billy Thomas The classic quote: “There are some people who meet that somebody that they can never stop loving, no matter how hard they try. I wouldn’t expect you to understand that, or even believe it, but trust me, there are some loves that don’t go away. And maybe that makes them crazy, but we should all be lucky enough to end up with somebody who has a little of that insanity. Someone who never lets go. Someone who cherishes you forever.”

Ally and Billy fall in love as little kids, and she follows him all the way to Harvard Law, even though she has no personal interest in becoming a lawyer. Then Billy transfers to the University of Michigan, where he meets and marries another lawyer named Georgia. Years pass, Ally randomly ends up joining the firm where they both work, and falls hard for Billy all over again. She dates plenty of guys during the show’s first few seasons, but Billy remains the love of her life. Then Billy’s marriage ends, and just when it looks like they might finally get together, he’s diagnosed with a brain tumor and dies in Ally’s arms in a courtroom — after delivering a gut-wrenching speech about how she was the love of his life. Is it really any wonder that this woman sees dancing babies?

Ted Mosby in How I Met Your Mother The object of his obsession: The anonymous Mother The classic quote: “If a cockroach and a mouse can find love in this crazy world, then so can I.”

Seven seasons in, we’re still unsure who the titular “mother” of this series might be, but we do know that she has something to do with a yellow umbrella and a wedding, and that she’s already crossed paths with Ted at least twice — at a St. Patrick’s Day party in 2008, and on his first day as a professor, when he was in the wrong room. What we have seen are the endless humiliations he’s willing to endure in his dogged search to find his soulmate. Just off the top of our heads, he’s dressed up like a “hanging chad” year after year for Halloween, been left at the altar, stolen a blue French horn, and, most recently, awkwardly confessed his love for Robin, prompting her to move out of the apartment they both share.

Angela Chase in My So-Called Life The object of her obsession: Jordan Catalano The classic quote: “Love is when you look into someone’s eyes and suddenly you go all the way inside, to their soul, and you both know instantly. I always imagined I’d fall in love nursing a blind soldier who was wounded in battle. Or maybe while rescuing someone in the middle of a blizzard, seconds before the avalanche hits. I thought at least by the age of 15 I’d have a love life, but I don’t even have a like life.”

To be fair, Angela’s angsty outlook on life wasn’t all Jordan Catalano’s fault, but her brief relationship with him certainly contributed to the cause — just imagine how you’d feel if your crush didn’t want anyone to know that you were the girl who he was making out with in the boiler room. Jordan also slept with Rayanne, sang a song called “Red” that wasn’t even about Angela, and got Brian Krakow to write the love letter that he couldn’t. And yet, she still hopped in his Plymouth at the end of the show! Who knows, maybe they lived happily ever after. Or maybe he’s holed up all by himself in some Unabomber cabin in the mountains, making snow.

Dawson Leary in Dawson’s Creek The object of his obsession: Joey Potter The classic quote: “I don’t know. Are we more? Are we less? All I know is it’s just not the way it used to be. Nothing is anymore.”

Things were once so simple for Dawson. His childhood best friend Joey would crawl into his bedroom through his window, and they would watch old movies in his bed and engage in clever banter. Then a big city girl named Jen Lindley arrived in town, and he had what we’ll call a sexual awakening. Joey was jealous — even tagging along on their first date — and suddenly he had to choose between the two women. After a lot of soul searching (and thanks, in large part, to that beauty pageant), Dawson picked Joey at the end of Season 1, but it was arguably too late at that point — she had already experienced that surprise kiss from Pacey, a moment that teased the relationship that would later blossom between them in Season 3. What’s more, once Dawson and Joey finally became a “real” couple in the second season, it totally ruined things between them, and Joey decided that she needed to break up with him to “find herself.” They ended up getting back together, but then Dawson convinced Joey to wear a wire and get her ex-con dad sent back to prison, and they broke up again. After spending the summer apart, Joey tried to get back with Dawson, but he rejected her. That’s how she ended up secretly dating Pacey. Over the course of the following seasons, there were plenty of times when Joey seemed to consider ditching her passion with Pacey for the stability of her relationship with her oldest friend, but ultimately our protagonist didn’t get the girl next door — the show’s writers had her pick Pacey. Poor Dawson wasn’t left completely empty-handed though: he turned their story into a TV show called The Creek.

Carrie Bradshaw in Sex and the City The object of her obsession: Mr. Big The classic quote: “After we made love I knew it was over. Did I ever really love Big or was I addicted to the pain, the exquisite pain of wanting someone so unattainable?”

Yes, we finally get our happy ending (that is, if you were on Team Big), but wasn’t it just so exhausting getting there? First, Carrie breaks up with Big because he won’t tell her that she’s the One. Then she secretly starts dating him again, only to dump him again when he doesn’t factor her into his plans to temporarily move to Paris. Big surprises everyone by coming back from Paris engaged. He gets hitched and proceeds to cheat on his new wife with Carrie, who is dating a lovely furniture maker named Aidan. Carrie gets caught in Big’s apartment, effectively ending his marriage and her relationship with Aidan. Carrie and Big decide to try the whole friend thing for a while, and Carrie convinces Aidan to give her another chance (he buys her apartment; they get engaged), but she ultimately decides that she’s not really into it, and breaks things off again. Big moves to Napa. When he returns to New York for a medical procedure, Carrie realizes that she still has feelings for him, but then he leaves without saying goodbye, and she realizes that he can’t still commit. She meets a rich Russian artist who gives her the key to his apartment without even being asked, and whisks her away to Paris after only a few months of dating. Once they’re there, he pays more attention to his upcoming exhibition than her, and she gets lonely. The Russian accidentally slaps her. Big shows up in Paris because after six seasons, he’s finally ready to tell Carrie that she’s the One. We find out that his name is John. They live happily ever after — until the Sex and the City movie, that is.

Ross Geller in Friends The object of his obsession: Rachel Green The classic quote: “Look, I just don’t want my tombstone to read, ‘Ross Geller, Three Divorces.'”

For a paleontologist with a Ph.D. from Columbia, Ross can be pretty dumb when it comes to matters of the heart. When we first meet him, his wife Carol has just ended their marriage after falling in love with a woman who she met at the gym. He fills the romantic void in his life with a monkey named Marcel. Then, when Rachel starts dating a guy named Paolo, he realizes that he has feelings for her. He also kisses Chandler’s mom. He goes on a dig in China, and falls in love with a woman he went to grad school with named Julie. Rachel decides that she has feelings for Ross too, and he ditches Julie for Rachel — after making a list of pros and cons. Rachel finds the list, gets mad at Ross, and decides that she wants nothing to do with him. Then she sees a home video from high school, and realizes that Ross was going to take her to prom after her own date had bailed, and forgives him. They’re happy for a while. Then Rachel gets a job at Bloomingdale’s and Ross is jealous of her hot boss, Mark. They infamously decide to “take a break,” which leads to Ross sleeping with Chloe, a chick from the Xerox store. Then Ross and Rachel really breakup. Ross eventually starts dating a girl named Bonnie, who Rachel tricks into shaving her head, because she’s secretly still in love with Ross. Rachel writes Ross a really long letter demanding he take full responsibility for everything that went wrong in their relationship; he agrees to it without reading the letter. Once he does, he’s furious, and they break up yet again. He meets Emily, Rachel’s boss’ niece from England. Whirlwind romance ensues! Ross ends up proposing to Emily but saying Rachel’s name at the altar. Thus begins a long period of Ross trying to get back with Emily that inexplicably ends up with him drunkenly marrying to Rachel in Las Vegas. He lies to her about getting an annulment because he doesn’t want another failed marriage. Eventually, Rachel finds out that they’re still married and they file for divorce. This is around the time Ross starts dating one of his students, Elizabeth Stevens. Nothing of note happens with Ross and Rachel for a while, until they have sex while addressing Monica and Chandler’s wedding invitations, and Rachel gets pregnant. Around the time that Ross finds out, he starts dating Mona. He also asks Rachel to move in with him, which kind of kills things with Mona. Rachel has their baby, and Joey accidentally proposes to her. Season 9 goes by without much to report, but by the series finale in Season 10, Ross and Rachel are finally on the same page, if not in the same airport.

Felicity Porter in Felicity The object of her obsession: Ben Convington The classic quote: “Maybe getting over someone you’re in love with isn’t impossible. Unless, maybe you don’t actually get over it. Maybe you just learn to live with it.”

Cue up the Sarah McLachlan… Is there anything that can compare to the emotional highs and lows of the Felicity-Ben-Noel love triangle? It all starts when Felicity ditches her original plans for college and decides to follow Ben Covington, her high school crush, across the country after she reads the charming note he wrote in her yearbook. Once she arrives as the University of New York, she meets Noel Crane, her cute, geeky RA, and the kind of boring “nice” guy who she should probably be with. But everyone — including Noel — sees that she can’t help but be drawn to Ben. The next four seasons are a prolonged Ben vs. Noel/following your heart vs. your head debate so intense that the show’s creators gave us both endings. Yes, those time travel episodes in the final season were totally weird, but they also left us convinced that an alternate universe where Felicity ended up with Noel was not a universe we wanted to be a part of. Ben might have his issues (crippling insecurity! addictions to gambling and alcohol! a problem with commitment! an illegitimate child!), but at least they’ve got sexual chemistry. Unfortunately, that means Noel dies.

Bill Compton in True Blood The object of his obsession: Sookie Stackhouse The classic quote: “Sookie… I cannot and I will not lose you. For all the ways I have dismayed, aggrieved or failed you, I swear I will atone. But I am not sorry. I refuse to apologize for what you have awakened in me. You, you are my miracle, Sookie. For the first time in a hundred and forty years, I felt something I thought had been lost to me forever… I love you.”

Of all the bars in all of the world, he had to walk into Merlotte’s. Of course Vampire Bill fell hard for Sookie — first she saved him from being drained by Mack and Denise Rattray, then she drank his blood, connecting them for life. And for a while, things were copacetic. Bill’s biggest worry was keeping Sookie safe amidst all of the supernatural craziness constantly going down in Bon Temps. Then there was that adorable moment at the end of Season 2 where he proposed to her, and said that he didn’t care whether she was human or not, that he wanted her just as she was. Adorable. But that was before Sookie fell in love with Eric Northman or fell into bed with Alcide. Yes, there was once a time when we were excited to hear Bill shout “SOOKEH,” but these days we wish that he’d surprise us all by finally getting over her and finding another fairy to swoon over. It’s almost enough to make us wish Lorena could come back.