Five Dating Lessons From ‘Mad Men’

As Mad Men begins to wrap-up with only three episodes left in the series, I’ve been watching every episode twice. A few weeks ago a line Peggy Olson said struck me as totally out of sync with today’s times. Sure, Mad Men is filled with debauchery, but like Breaking Bad and Sex and the City, it balances consequences and rewards. The seven seasons of Mad Men have been amazing in their own ways. Nearly every scene is quotable, but not over-written. Here are five of my favorite quotes that provide lessons for dating in the 21st century.

“Take off your hat.”

Elevator scenes in Mad Men are wonderful because they are a way to bring characters together who might not ordinarily have a reason to interact. In one scene a couple of immature, younger men are engaging in locker room talk about women as Don Draper and an older woman stand silently in the elevator. They are unaware or ambivalent to how they might be making the woman feel. Don says, “Take off your hat.” Despite all of Don’s demons, the audience roots for him. It’s a scene reminiscent of this one from The Sopranos.

The lesson isn’t that you can get away with a lot of bad behavior as long as you have good manners. It’s that chivalry is not dead. Men: don’t judge all women by the one or two experiences you may have had with a woman who didn’t want a door held open for her. Most women and men are still drawn to traditional roles while dating. Don’t indulge dime-store feminists by letting these traditions end.

“So, you drive a truck?”

In season one of Mad Men, Peggy went on a date with a man from the neighborhood where she grew up. Peggy is eager to talk about her job, but she is not impressed with her date’s blue-collar job. It’s no surprise that he takes offense to the tone of her question, “So, you drive a truck?” Their dinner quickly becomes a competition rather than a date.

Women, especially in large metro areas like New York, Washington D.C., and Los Angeles, tend to put too much emphasis a potential partner’s job. A woman once told me that she wouldn’t date a guy who makes less than six-figures. It wasn’t that she was necessarily money-focused, but she used another person’s salary to determine whether he was her equal.

Rather than focus on salary, we should focus on qualities like ambition, ability to live within his or her means, and other values we admire. They often last longer than the job with the coveted salary.

“Call me when you get back to D.C.”

This is the line that sparked my interest in identifying Mad Men’s dating lessons. When I heard Peggy say this in a recent episode of the final season I was reminded of how different dating is now. In this scene, Peggy is having a romantic moment on yet another first date. They’re trying to figure out when they can see one another again. The man has a couple job interviews lined up in Boston and D.C. the next week. Not only does Peggy show confidence by asking him to wait, she also gives us a look into dating in a non-texting world.

Now that we have the ability to be in constant contact, we tend to think there’s something wrong if we’re not connected to one another 24/7. Rather than confidently saying, “Call me next week” and men actually calling, women and men are deciphering the meanings of emojis.

Certainly after two people are in a committed relationship any form of communication that’s most convenient for them is good. However, when getting to know someone texting should be used for convenience, not as a way to move a relationship forward.

So, men, call us. Women, wait for the man who calls you and ignore the ones who only send 2 a.m. texts.

“I’m not a solution to your problems. I’m another problem.”

When Roger Sterling is feeling down, he turns to Joan Harris. Though Joan is younger, she is wiser after many years of being the other woman. Her heartfelt response to Roger’s advances in season four showed that she was ready to move on, while also acknowledging her part in the past. She told him, “I’m not a solution to your problems. I’m another problem.”

It’s tempting to choose short-term pleasure or comfort over the goal of a long-term, healthy relationship. In Finding Mr. Righteous, I wrote about how I wasted a lot of time on indulging new problems rather than solutions. To paraphrase playwright and Ambassador Clare Boothe Luce, when we’re feeling down, we often look for a different reflection of ourselves in another person’s eyes. Though painful and sometimes lonely, it’s better to deal with our reality.

“The day you sign a client is the day you start losing them.”

In the first season of Mad Men, Roger said this line to bring comfort to Don, but it’s also a warning. After going through the dating trenches, it’s easy to understand how some men and women want to take it easy once they’re in a committed relationship. However, like a client relationship, a romantic relationship should always be nurtured. Whether it’s a break-up, separation, divorce, or death, you never want to be left wishing you had done more.

When I read stories of long, successful marriages the couple often talks about the little things. Instead of talking about a gorgeous, expensive piece of jewelry she received one Valentine’s Day, she talks about the time he brought her a single flower for no reason at all.

But, women, it should never be a one-way street. Millionaire Matchmaker Patti Stanger suggests that for every four dates the woman does something nice for the man. My view doesn’t require as much math, but it’s a good place to start.

Finally, the most important lesson on dating comes from Don. Not all relationships are perfect or forever, but despite past heartaches and the uncertainty of the future one must always “move forward.”


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