The Very Best and the Absolute Worst Couples of ‘Mad Men’

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Not including the sad divorce of Ginsberg and his nipple.

We're only halfway through the seventh and (weep) final season of Mad Men and already there's been enough relationship drama to last us through the upcoming hiatus and then some. From Bob's not-great sham marriage proposal to Joan (she declined, thankfully) to Megan and Don's desperate threesome, to Pete and Bonnie's (seemingly short-lived) mile high romance, to Peggy's terrible, horrible, no good, very bad Valentine's Day, the folks on Mad Men continue to have the most up-and-down relationships in all of television. In honor of this Sunday's mid-season finale, we've picked out the best and worst couples in Mad Men history. Don't forget to watch it with someone you love – or love to hate but can't seem to live without. (See: Don Draper.)



Joan and Roger

Won't these two crazy kids just work things out? No, their on-and-off relationship is not ideal (they both cheated on their respective spouses with one another at different points), but their sexual chemistry is off the charts (remember that rendezvous in the alley after they got mugged?) and you can just tell they genuinely care about one another. Plus, you know, that whole secret love child thing. C'mon you two, if you're not going to get together for us, at least do it for little Kevin.

Ken and Cynthia

Perhaps the only functional, couple in it for the long haul in the history of Mad Men, Ken and Cynthia are not only faithful to one another (the rarest Mad Men jewel of all), but they actually seem to genuinely like each other. They've stuck it out through good times and eye patch times, and the happily married couple has since become happy new parents. Maybe Ken was on to something with his sci-fi writing: have a side hobby so that the soul-draining work at Sterling Cooper doesn't have a negative effect on your home life.  

Ida and Young Roger

Oh, Ida Blankenship, you hellcat. Thanks to the reveal in the recordings for Sterling's Gold that Ida was "Queen of Perversion of the highest order," we got a glimpse of the greatest love Mad Men triangle that never was: a young Roger Sterling, a sexually charged Ida Blankenship, and a ball-less Bert Cooper. In her old age Ida was cranky, pretty damn terrible at her job, and a little bit racist, but from the sounds of things, she turned some heads – namely Roger's, as he used his own self-proclaimed "prowess" on her – in her heyday. In fact, Ida left such a mark on the men of Sterling Cooper, she inspired her old boss Bert to give one of TV's greatest eulogies: “She was born in a barn in 1898 and died on the 37th floor of a skyscraper. She was an astronaut."

Sally and Glen

Sure, Creepy-Ass Glen is so very creepy but, unlike so many people in Sally's young, troubled life, he does genuinely care about her welfare (especially now that they're a little bit older) and has always looked out for her, even when she's getting into trouble of her own. Not only has Glen defended Sally's honor over the years (and gone out of his way to sneak out to see her), but it seems he even cares about her in a non-creepy Creepy Glen way.

Don and Faye

Poor, poor Faye Miller. Smart, beautiful, funny Faye. Perhaps the only woman in the entire world, aside from Anna Draper and Peggy, who could have made Don a healthy, decent man. Don knew that too (Faye was something special) and cut and run as soon as he started to let her in and see the real him. The consumer research consultant had a hot-and-heavy affair with Don that turned into something so much more, but instead of marrying her he went and married Megan instead. Sure, Faye and Don didn't make it, but it was good while it lasted until, well, it didn't. Because, as Faye so perfectly put it, Don "only likes the beginning of things." She had that man figured out.



Don and Literally Everyone Else

Sheesh, where to begin?! This serial philanderer had a failed marriage to Betty, about a dozen very emotionally and physically reckless affairs (most recently, to his neighbor and friend Sylvia, which poor Sally accidentally had a front row seat for), and a wandering eye and closed-off heart that has made him poison for just about every woman he's crossed paths with. From his former scorned secretary Allison to his struggling second wife Megan, there's a price to Don Draper's good looks, and all of the women in his life have paid the price one way or another.

Betty and Henry

Betty's rebound marriage to Henry is ultimately way healthier than her marriage to Don (even though she did slip in a one night stand with her ex-hubby) and he was incredibly sweet and supportive during the infamous "Fat Betty" phase – but in the dramatic world of Mad Men these two are just so unbelievably boring.

Sal and Kitty

Joan may not have been willing to be a beard for Bob, but Kitty sure did for Sal back in the show’s early seasons. Not only were we aware of Sal's true sexual orientation (the bellboy he started to hook up with made that pretty clear), but so was poor Kitty. Still, she persevered and put up with the charade even when Sal became worse at hiding it. One of the more tragic Mad Men couplings, and that's really saying something.

Pete and Trudy

Even though they had some pretty sweet dance moves together, their good-on-paper marriage crumbled pretty spectacularly given that Pete is a no-good, cheating dweeb with serious daddy-in-law issues. On the bright side, Pete helped turn Trudy from a squeaky-clean Suzy Homemaker into someone who can now stick up for herself and no longer take any of Pete's shit.

Peggy and Ted

Peggy has nothing but terrible relationships on Mad Men, from her inappropriate affairs with colleagues like Duck (yuck) and Pete (which resulted in a secret pregnancy) to her doomed courtships with twerps like Mark and Abe. Still, nothing stung quite as badly as her affair with yet another married coworker, this time in the form of Ted. These two had incredible chemistry and, unsurprisingly, fell head over heels for each other, but Ted couldn't leave his wife and kids for her, and instead moved himself and his family all the way across the country just so he didn't have to face her on the regular. Once again, Peggy got left with all the heartache, while the man who treated her poorly got to walk away unscathed and with someone to love. Just get together with Stan already wouldja, Peggy?

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