10 Ways To Rebuff (Or At Least Rebound From) The Bad Boy (According To Don Draper’s Many Women)

Alright, the surest way to not be hurt by a bad boy is to turn on your heels as soon as you spot him and run far and fast in the other direction – especially if he’s married. But if you can’t resist getting even a little close to the flame, then learn from the mistakes of the women who fell for the charms of the über bad boy in the gray flannel suit: “Mad Men”‘s Don Draper.

He’s had countless one night stands – from prostitutes to secretaries to executives – but led a chosen few to believe that they were each “the one.” These smart, attractive, educated women were sucked in by his charms, but luckily they got out with their dignity, or at the very least, their sanity intact. Here’s how they did it.

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1. Find A Replacement

Comic Jimmy Barrett once asked if Betty and Don “were sold separately.” They did have a doll-like perfection, and when their biorhythms were in sync, there were, as the Grace Kelly look-a-like once noted, “a good team.”

The rest of the time, Betty was a bitch, greeting her husband with a puss and a flick of her cigarette ash, resentful that he was out in world working and cheating, while her brain that earned her an anthropology degree and model good looks were going to waste on children she couldn’t relate to and gossipy frenemies who bored her.

She really saw no way off her June Cleaver hamster wheel until Henry Francis made a pass. Yes, Don called her a whore, gave her a shove and told her to get out; but she ended up with the kids, an even nicer house, and a man who only has eyes for her – even when she packed on the pounds and dyed her hair Liz Taylor-black.

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2. Be Realistic From The Get Go

He was an uptown guy and she was a downtown gal, but Midge was no boho bimbo. She couldn’t/wouldn’t be conned into some “fly away with me” line of BS. She was in Greenwich Village to stay.

The graphic artist/painter enjoyed her and Don’s opposites attract liaisons, but kept her heart below 14th Street. As Don observed when he saw Midge with one of her ilk, “I know you’ll never look at me the way you look at him.”

She took his check and said goodbye in a “here’s your Fedora what’s your hurry” kind of way. She resurfaced only once, not for love, but again for money to feed her unfortunate heroin addiction. Midge had her priorities. Don wasn’t one of them. Never was.

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3. Treat Him As An Equal

She could do bad all by herself. Hence, Bobbie Barrett didn’t put the handsome ad man on a pedestal. They were on the same level. She gave as good as she got, and even got one over a time or two. Plus, Bobbie had a husband, so she wasn’t looking for a commitment, just a fling.

In fact, she valued the relationship so little that Bobbie not only spoke of it openly, but rubbed in Don’s face just how indiscreet she was. Sure, he left her tied to a bedpost in some midtown hotel, but not before she hit him where it hurt in the trust department.

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4. Take A Hint

Three dates in half a year. Bethany wanted to give her older guy time get his post-divorce footing. That’s why after their first setup, when her hard-to-get act didn’t get him to call anytime soon, she gave him another chance, only to end up disappointed that he took her to a loud, hardly intimate dinner at Benihana.

Months later, the aspiring actress said yes one last time. Although this restaurant was more to her liking, they ran into Betty, and Bethany was horrified to see that she was Don’s ex’s younger doppelganger. The childlike blonde was also let down by her date’s unconcerned reaction to her demand that they see each other more, in order to get to really know each other.

The backseat oral sex was the final test: it would either have him coming back for more immediately or be a lovely parting gift. (It didn’t and it was.)

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5. Know When To Walk Away

Suzanne let Don know that he wasn’t special right from the start by pointing out that he was like all the other flirtatious dads: “You all even wear the same shirt.” Yet there she was, drunk dialing, then sneaking him into her garage apartment.

Indeed, the teacher got schooled by actually believing they were going to have a life together, but when he “dropped by the house to pick up a bag” and never came out, Suzanne got out of the car with out histrionics, took a long last look behind her, then walked with purpose into the future.

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6. Get A Life

Beauty. Brains. A high-powered career. Rachel had a lot going for her. She was a straight arrow who saw Don as a walk on the wild side; the forbidden fruit to her Jewish heritage. So when he dangled the “let’s get out of here” carrot in front of her, the non-desperate fashion mogul was smart enough to see that he didn’t want to run away with her, “You just want to run away.”

Insulted, and unwilling to be his excuse to leave his marriage, Rachel ended it right there and then.

By the time the exotic beauty met with her untimely death, she’d met a man named Katz, and had added wife and mother to her resume. As her sister told Don, “Rachel had everything she wanted.” Unlike him, who had only the memory of the one that got away.

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7. Accept He Won’t Change

She was a new beginning. A breath of fresh air. Don’s second chance. As Joan said of Megan to the receptionist: “I know a girl who had your job and now she has everything.”

Megan did get it all: A handsome, rich husband, a palatial Park Avenue apartment and a coveted advertising job, plus a man who drank, cheated and took pleasure in being condescending and dismissive.

New wife. New life. Same old Don.

When he assured the promising actress a move to California, then reneged, she went without him, distancing herself mentally and emotionally as well.

In the end, Megan got to tell him off: “You’re an old, sloppy, drunken liar.” That was worth a million – literally and figuratively.

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8. Don’t Mistake Yourself For Special

Self-sufficient, confident and professional, Faye’s job was to read people by translating what they said into what they really meant. She saw Don for what he was – a motherless boy in a grown man’s chiseled body. She gave him what he needed: physical and emotional stroking, an introduction to a prospective client, then nursed him through one humdinger of an anxiety attack.

Faye thought the deal was sealed when he confided in her about his true identity. (FYI: He also revealed his past to Betty, Megan, and Rachel. Pete Campbell knew, as did Burt Cooper, the Hershey’s client and who knows how many others. It’s hard to fathom how Don walked down Madison Avenue without most of New York waving, “Hi Dick,” that’s how big a “secret” his life seemed to be.)

Faye was totally blindsided by Don; not just his breaking up with her, but by announcing his engagement in the next breath. Indeed there were tears, but her steely resolve enabled her to walk into Sterling Cooper to collect her things with her head held high

When Peggy asked if they could stay in touch, Faye gave a terse, yet polite, “No.” Self-preservation required that she never again see Don or anyone associated with him.

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9. Don’t Care Too Much, Or At All

Sure he’s easy on the eyes, rich and slick, and she could only be described as poor, downtrodden and alone, yet Diana still had the upper hand.

She didn’t try to impress Don, but did anyway. She switched jobs and he tracked her down; insisted upon seeing her every night; and wanted to hear about her past more than he wanted to share his.

Di called once, at his request. And merely rolled her eyes when she had to hightail it out of his bed because Megan was on the way.

When he showed up at the one room dump Diana called home and offered to take her away from all this, she shrugged. Given the choice of being happy with Don or miserable without hi, well, Di hoped the flophouse door wouldn’t hit him in the back on the way out.

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10. Leave The Minute It Stops Being Fun

She was beautiful and bored. Sylvia couldn’t compete with her husband’s substantive mistress: his career as a life-saving surgeon. Her only child was away at college, which meant the Draper’s upstairs neighbor had time on her hands.

Don’s lurking by her backdoor was a thrill. Carrying on their affair in her boy’s old room took illicit to the next level. And even being caught by Don’s teenage daughter, Sally, added to the cachet of their untoward affair.

But when he stranded her in the hotel room for hours, made her crawl on all fours to him, and initiated some “50 Shades” sex game, Sylvia stifled a yawn, put her dress on and went home.

Lorraine Duffy Merkl is a NYC freelance writer and author of the novel FAT CHICK.