Valentine’s Day: TV boyfriends who messed with our heads

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They're heartbreakers, dream makers, and love takers. And they're the worst TV boyfriends ever! In honor of Valentine's Day, check out these bad boyfriends of the small screen who really messed with our heads.

Don Draper

Let's face it, for most of his boyfriend career, "Mad Men's" Don Draper wasn't even single. The married-with-children philanderer (played by Jon Hamm) bedded every woman in town, including his daughter's teacher! But once he divorced his wife Betty, Don's womanizing ways didn't stop. He finally found what we thought was a keeper in psychologist Faye Miller, but when the relationship became too healthy and normal, he dumped her -- over the phone -- for his young secretary, Megan. A bitter Faye analyzed the situation quickly: "I hope she knows you only like the beginnings of things," she seethed. We say this doc dodged one really hot mess!

Mr. Big

On HBO's "Sex and the City," Carrie Bradshaw dated a swamp of frogs before she found her Prince Charming. Or did she? When it came to her slew of really bad boyfriends, you'd think Jack Berger would top the list (he broke up with her via Post-It note, after all). Even that narcissistic creep The Russian, who swept her off her feet and off to Paris before breaking her heart and her necklace, was hard to root for. But no, the long-suffering Carrie's worst boyfriend was the guy she eventually married.

Mr. Big (played by Chris Noth) put this girl through the wringer, even marrying a 25-year-old model right under her nose. Carrie took him back time and time again, and when he finally decided he'd had it wrong all those years ("It took me a really long time to get here, but I'm here. Carrie, you're the one," he told her in series finale), Big saved his slimiest move for the big screen. Yes, they eventually married, but not before he jilted her.

Jordan Catalano

The incessantly out of it Jordan Catalano (played by Jared Leto) probably didn't come equipped with the tools to be a good boyfriend (he was a stray puppy-type who specialized in blank stares), but Angela Chase still kept trying to fix him. Hence the teen head games on the 1994 coming of age drama "My So-Called Life." While Catalano had our hearts melting when he finally made a commitment and grabbed Angela's hand in the school hallway, it wasn't long before he committed the worst boyfriend sin ever and hooked up with her BFF, Rayanne Graff. The show was canceled before we saw how things panned out in this high school love triangle, but is it wrong to hope that Angela somehow ended up with Brian Krakow?

Chuck Bass

A narcissistic Upper East Sider, "Gossip Girl's" Chuck Bass (Ed Westwick) was a preppy teen womanizer who specialized in lying, cheating, and stealing. Talk about a heartbreaker, love taker -- literally! But what else would you expect from a guy who says things like, "The idea of unconditional love is as quaint as the tooth fairy or environmentally friendly dry cleaning?" The series finale featured a five-year flash forward, which showed Chuck and on-off love Blair married and the parents of a son, Henry. Of course, Blair originally married Chuck to avoid testifying against him. They don't make Hallmark cards for that kind of love.

Any star of "The Bachelor"

We know, we know -- the reality dating show "The Bachelor" is supposed to be about one man's journey to finding love, and it comes complete with dream dates and jet setting that would make any heart swoon. Still, how can you be a good boyfriend if you're swapping spit with 25 different women? By the time this show gets to the hometown dates and fantasy overnights, the pool is whittled down big time, and real feelings are involved -- or so they say! But the poker-faced star still has to hide his feelings from his true love for fear of spoiling the Neil Lane encrusted final rose ceremony, which translates to him to leading on the remaining girls.

This doesn't go over well months later, when "The Bachelor" and his now-fiance watch the episodes together, and she sees him making out with another girl just one night before he proposed to her! Suffice it to say, in the end, most of these bachelors remain bachelors. Bad "Bachelor" hall of fame: Jason Mesnick, who dumped his final pick on camera and swapped her for his runner-up.

More from this contributor:

10 things to know about 'Mad Men'

'The Carrie Diaries' vs. 'Sex and the City': Dare to compare

'Private Practice' series finale: Other TV shows that ended with a wedding

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