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Jack Donaghy and Sally Draper Romance

When Jack Met (Adult) Sally: An Imagined Romance

Mad Men and 30 Rock crossed paths when Jon Hamm played Liz Lemon's boyfriend, the unlovable Dr. Drew Baird. Now a fan has taken it one step further and about five steps weirder by writing a short story about the love affair between 31-year-old Jack Donaghy and 36-year-old Sally Draper. It's long, so I highlighted my favorite parts and spared you the "action" details.

It's the Spring of 1990 and the recently separated Jack Donaghy and Sally Draper meet at the Met.

Sally turned out to be an English teacher at a Montessori school on the Upper West Side, but this slightly unpleasant revelation was not enough to make Jack reconsider.

Read the rest after the jump.

After a few weeks of dating, Jack goes back to Sally's apartment.

"You should talk to my father."
"I thought you didn't talk to your father."
"I talk to him, I just don't—you know, talk to him. We're not close, but we're not estranged or anything. Anyway, he was in advertising for a long time, and I know it still interests him..."
"Oh my God," Jack said. "Your father isn't—"

Jack meets Don Draper, now in his sixties, for branding advice. Talk turns to Sally.

"You're a different sort of person for Sally. I think her therapist might try to discourage your relationship."
"Because I don't believe in psychiatry?"
"Don't you?" Draper asked. "No, because she goes to a Freudian psychoanalyst who'll probably tell her you're a lot like me. . . ."
"Do you think I'm a lot like you?"

I'd include their breakup, but this is indeed fiction as the story ends with them together. Oh, and Don? He gets lung cancer.

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Join The Conversation
cupcakers cupcakers 5 years
haha this is so weird. I know Sally is suppose to be older and Jack a bit younger, but that picture of them above-can't help but think it's inappropriate! ha. I love both shows. Jack Donaghy would totally go for Betty or Joan for sure
cupcakers cupcakers 5 years
haha this is so weird. I know Sally is suppose to be older and Jack a bit younger, but that picture of them above-can't help but think it's inappropriate! ha. I love both shows. Jack Donaghy would totally go for Betty or Joan for sure
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