Matthew Weiner's exceptional Mad Men introduces the viewers to the exciting world of advertisement in the 1960s New York City. It's a man's world, and women are only starting to find their place in society as a whole. Most characters have unhealthy habits, especially by today's standards.
Drinking, smoking, and cheating on your spouse are all considered pretty normal behaviors, so it would be hard to find a like-minded friend on Madison Avenue with a modern mindset. Regardless of their cultural shortcomings, some characters on Mad Men would certainly make for amazing friends. Others, however, were far too secretive, sexist, and insecure, so they'd best be avoided.
Befriend: Joan Holloway
While Joan's condescending treatment of other women is something that would never fly today, Joan has a lot of qualities people want in a friend.
She is fiercely independent, organized, poised, and elegant. As is evident from her relationship with Peggy, she always gives thoughtful advice and keeps people's secrets to herself.
Avoid: Betty Francis
Of all the Mad Men characters, Betty was the most resistant to the changes that the '60s brought. Even though she felt like a caged bird and was clearly repressed, she kept up the perfect housewife act almost until the very end. The divorce from Don left her feeling bitter and she became short-tempered and mean.
Even though Betty is not a bad person, it would be hard to be her friend in real life. Most of the time, she acted like a child and valued appearances more than anything else.
Befriend: Bert Cooper
The eccentric founder of Sterling Cooper served as an anti-thesis to Don Draper and all the ego-driven men on the show. Rather than getting caught up in his emotions, Bert remained level-headed and distant.
He knew how to enjoy the little things in life and deeply admired the Japanese culture. He didn't speak unless he really needed to. His sanguine presence brightened the office and the lives of the people he touched. Bert would definitely make for an outstanding dinner guest.
Avoid: Pete Campbell
In the beginning of Mad Men, Pete was without a doubt the least likable character. He was immature and insecure, desperately hungry for power and success. He couldn't be happy for other people. When Ken Cosgrove's short story got published, he couldn't hide his frustration.
The saddest thing about Pete is that he tried to do what was expected of him, but that only made him even more miserable. As the show crept to its end, Pete Campbell realized just how misguided his approach to life was all along. He underwent a major transformation and ended up as a man who just might make for a decent friend - but not quite.
Befriend: Trudy Campbell
Trudy Campbell is a genuinely good person, which is something that can't be said for a lot of Mad Men characters. Even though she leads a traditional lifestyle, she's no meek housewife. Clever, outspoken, and witty, Trudy always got what she wanted without being hostile.
Who wouldn't want to be Trudy's friend? She is loyal, honest, and cheerful. She's the type of woman who truly believes in her friends and wants only what's best for them.
Avoid: Harry Crane
Harry Crane's arc is the opposite of Pete's. He started out as a kind, respectful, and humble man, but as he rose through the ranks, he became arrogant and mean. At work, he often wanted to take credit for someone else's work.
From his sexist remarks to his shameless infidelity, there are countless reasons why Harry is not somebody most people would find pleasant. What makes him different from other casually racist and sexist characters is that he doesn't seem to have any redeemable qualities left by the time the show ends.
Befriend: Peggy Olson
Peggy is the youngest of all the main characters, so at the beginning of the show, she is a bit immature and naive. She's not as warm and friendly as Trudy, for example, but she would make for a great friend nonetheless.
She's smart, inquisitive, and ambitious. People who would consider themselves progressive in her time period would be delighted to find a friend in her as she makes for a great conversationalist and isn't afraid to try new things.
Avoid: Greg Harris
Fans generally agree that Greg was insufferable from the very start, but Joan married him anyway. He was a handsome, educated man and as such, a catch. What he didn't let others see was just how insecure he was. He felt threatened by Joan's independence and raped her after she introduced him to the people around the office.
After they tied the knot, he abandoned Joan and joined the army where he could feel like he's contributing to society as a doctor. Judging from his relationship with Joan, Greg wouldn't make for a good friend. He harbored dark secrets and was constantly drowning in feelings of ineptitude.
Befriend: Roger Sterling
Just a quick look at Roger Sterling's best quotes is enough to agree thathe would be a great addition to anybody's friend group. He's endlessly funny, adventurous, non-judgemental, and charismatic.
While Roger has a great presence, he's not the type of person who'd go over and beyond for his friends. He would, however, make for a great travel buddy!
Avoid: Don Draper
While fans loved Don's creativity and charm, he would definitely not make for a great friend in real life. He was dismissive of everybody who wanted to get close to him, even of his own little brother Adam.
Don wasn't a horrible person, he just had a lot of inner demons. He refused to show his vulnerability, which made it impossible for him to connect with others on a deeper level. Those who tried got hurt, so it would be best to avoid him at all costs.