25. Midge Daniels
My wife is a sucker for the whole artsy bohemian thing, and once she found out I never actually read “Last Exit to Brooklyn” I could tell she started thinking the grass was greener in Midge’s pastures.
24. Jim Cutler
It’s like sleeping with Roger, except he’s a Roger without a soul, so you know he won’t fall for you. I can see the appeal.
23. Harry Crane
If it’s a “she’s leaving me for someone else” affair there’s no way it’s Harry, but if it’s an “I’m cheating because I hate myself” thing Harry is the prime suspect. It’s a coin toss, which lands Crane squarely in the middle of the list.
22. Helen Bishop
I can definitely imagine my wife and Helen activating each other into a full-blown Thelma and Louise thing. Lord knows I’ve masturbated to it countless timesbefore.
21. Bonnie Whiteside
Honestly, this is the exact affair my wife needs. Just a low-stress fling with an ambitious grindset type that will reinvigorate her confidence and energy but also remind her how much deep down she misses me. Please oh please let my wife just be cheating on me with Bonnie.
20. Marie Calvet
She’s French, she’s mean, she loves cheating on her husband—a triple threat. Then again mean foreign mature adultress is way closer to my PornHub search history than Tiffany’s. Does anyone have Marie’s number?
19. Faye Miller
Research shows that my wife might be sleeping with Faye as a way to appease her latent death-impulse.
18. Megan Draper
Like me, she’s an unstable dreamer, but unlike me, she’s had some success in her acting career and is a total smokeshow. Could my wife be having an ill-fated May-September romance with Don’s 2nd wife? She CLAIMS Megan only sang “Zou Bisou Bisou” to her at that birthday party as a FRIEND, but I have my suspicions.
17. Mona Sterling
Roger’s jilted ex was always one of my wife’s favorite characters on the show and she always got really weird when I pressed her as to why. Was she merely sympathetic toward a woman trapped in a marriage with an irresponsible man-child for I can’t possibly think of what reason, or is there something going on between my wife and this fictional character? Maybe I should give our savings to a private investigator to find out. Or better yet, start my own detective agency! Oh man, that would be so cool!
16. Suzanne Farrell
My wife’s whole vibe has been different lately. She’s walking around with this sense of satisfaction and serenity as if she’s finally been truly seen and accepted for the first time. I don’t like that one bit. Makes me think she’s off having an affair with that empathetic grade school teacher from “Mad Men” or something. Wait, am I a good husband?
15. Freddy Rumsen
Based on how much my wife has been critical of my drinking over the years, one look at Freddy’s 2-year AA chip and she’ll probably swoon.
14. Anna Draper
She’s a California free-spirit type who is no stranger to unconventional relationships. They’re probably sparking a fat J in bed right now, mocking me.
13. Conrad Hilton
Yes, I’m aware that Conrad Hilton was a real person and yes, I’m aware that he’s long dead. I’m not implying that my wife is sleeping with Conrad Hilton the dead man, that would be insane. What I suspect is that she’s cheating on me with Conrad Hilton the CHARACTER from “Mad Men.” There’s something about his massive success despite total insanity energy I can see her falling for. It’s either him or the MyPillow guy, I’m pretty sure. Maybe I need to up my Adderall.
12. Richard Burghoff
Never underestimate the ability of a guy with a collar popped over his blazer and a bag of cocaine to bed your wife.
11. Lane Pryce
It’s the accent. It’s not just a British accent, it’s THAT British accent. There’s such a sad little music to it, honestly, I don’t even think I could stay mad at the guy.
10. Bob Benson
Yes, we all know what team Bob bats for, but he’s aggressively on the hunt for a beard, and as my wife often delights in telling me, she thought I was gay for the first year we were together.
9. Lee Garner Jr.
Lee is a predatory pig-headed closet-case and my wife knows few things would humiliate me more than helping this sadistic sack of shit keep appearances in exchange for a carton of Lucky Strikes.
8. Ken Cosgrove
Oh, sure, because he’s published right? Well, I’m sorry Tiffany, but if you can’t see how every rejection letter for my manuscript of “Time Jump: an Atticus King Story” is the PUBLISHER’S loss and not mine then Kenny can have you!
7. Henry Francis
Sometimes I worry that while I’m over here doing the WORK, reluctantly agreeing to bi-weekly date nights and considering giving in to my wife’s incessant pleas that I go to therapy, she’s out there building herself a lifeboat with Henry. Then again, she’s not blonde, which would hurt Henry’s political chances as a conservative.
6. Pete Campbell
If I ever meet him I’m going to call him a grimey little pimp and challenge him to fisticuffs. Also, he may have fucked my wife. Honestly, that has nothing to do with my desire to hit him. I know we’re supposed to sort of like Pete by the end of the show but part of me will always want to roll up my sleeves and find out how blue that blood really is.
5. Ted Chaough
She’s read “50 Shades of Grey” so I know she would be turned on by a guy who flies his own plane, and she married me so I know she’s got a thing for unstable train wrecks.
4. Betty Draper
When people fall in love with Betty they tend to fall deeply. An affair with Betty would explain my wife’s recent walking-on-clouds attitude and the lock of blonde hair I keep catching her sniff.
3. Roger Sterling
Nothing makes my wife remember her last batch of flowers is wilting faster than a silver fox charmer who thinks he’s smart and very much isn’t. Ever since she started making me incorporate a “My Old Kentucky Home” blackface routine into our love play I haven’t been able to shake my suspicions.
2. Peggy Olson
My wife loves a fixer-upper, and I’m well aware it was my myriad of personal problems that drew her to me in the first place. Now that she’s successfully trained me to keep all of my dirty laundry in one corner and actually do my taxes, she’s bound to be bored and looking for a new project. Enter the Everest of personal problems, Mount Peggy.
1. Don Draper
Armed with only insane attractiveness, Don rose to the top of the business world, and despite being an undeniable 11 out of 10 is only pre-requisite for sleeping with a woman is that she’s cheating on someone. This one hurts because my wife knows full well I would be fine with it if she just let me watch.
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