While the main focus of Mad Men might be on the cutthroat business of advertising, where nearly all the men are womanizers and have no problem sleeping with as many people that aren’t their wives as possible. However, that doesn’t mean that they aren’t able to put on the charm as well.
There’s a reason that the men are able to tie down some incredibly attractive and powerful women on the show, and that’s through romance. While they’re not faithful or overly caring, when they want to be, many of the main characters can throw on the charm offence.
Whether it be expensive gifts or lavish trips, they certainly do know how to treat a woman, and within this list, we will highlight that. So, let’s take a look at the 10 biggest, and best romantic gestures on the show.
Don’s Proposal
Anytime there’s a proposal on a television show, it’s always going to be classed as one of the biggest romantic gestures of the series. Throughout Mad Men, we only see Don pop the question once, and of course, he does so in a great manner.
While the moment itself isn’t thought out or romantic, it is heartfelt. Using a ring that means a lot to him personally, he rushes into the decision after falling head over heels in love with Megan. While it was arguably too soon, it certainly was romantic.
LSD
Taking LSD might not seem like a big romantic moment, but it certainly was for Roger and Jane. This was something she was desperate to do, and despite the risks involved and his hesitancy to do it, Roger eventually agreed and took the drug with her.
It leads to a totally bonkers set of scenes as he trips out on the drug, and it does actually lead to them getting divorced. However, despite the fact it causes their break up, it is arguably the only time they are brutally honest with one another, and it does create a romantic connection.
Putting On A Show
It isn’t just the men of the show that know how to work a romantic moment, as the women certainly do their share of romantic moments as well. One of the best comes from Megan Draper when she throws Don a surprise birthday party, which doesn’t actually go down very well.
Despite the fact he hates the entire situation, you cannot blame her for trying as she certainly goes all out. Hiring a band, inviting all his friends and then putting on one hell of a performance that has everyone man in the room leaving incredibly jealous of him.
Secret Gifts
The relationship between Roger Sterling and Joan Holloway is a complicated one that is shrouded in mystery. They clearly have strong feelings for each other but opt to keep things a secret all the way through the show, with Roger even getting her pregnant.
However, one thing that is consistent is Roger’s love for spoiling her. He showers her with gifts constantly throughout the show in order to keep her exclusive, from diamond earrings and necklaces to fur coats or dresses, and for a long time, it is enough for her.
Fixing The Dress
Often, the most romantic moments throughout the show are done with the worst intentions, and this is a prime example of that. When Trudy is away, Pete Campbell takes the opportunity to try and charm the neighbors’ au pair, working hard to fix her dress.
This leads to him bumping into Joan where he has to lie. However, for the most part, Pete seems to be doing the right thing. However, it ends up being a big romantic gesture to simply try and end up sleeping with her, rather than being nice for the sake of it.
Henry Moves Homes
This is a moment that often goes underappreciated on Mad Men, mainly because Henry Francis isn’t one of the featured characters on the show. Because he is seen as someone who took Don’s spot, he isn’t always looked at as fondly by the fans.
However, the fact he is willing to totally uproot his life for Betty and her family shows just how much he cares. He not only takes on the responsibility of three children but moves home when Betty decides she is fed up of living there, which is a huge gesture.
Meet The Father
Throughout Mad Men, the show really does a great job of highlighting the unfortunate racism that was rife around that time period. The show also does a great job of highlighting how certain people bridged that gap, and one of those was Layne Pryce.
He began dating Toni Charles while the rest of his family lived in England. While cheating wasn’t the best, he did try his best to show her proudly to his father. It might not seem like a big moment, but considering the time period and the beating he took following the announcement, it’s clear how big of a step this actually was.
Travelling
Glen Bishop is a complex character throughout Mad Men, who does spend most of his time trying to impress Betty Draper/Francis, despite their age difference. However, he does also have a very close relationship with Sally Draper as well.
So much so that he travels alone into the city to meet Sally for them to have a one on one date. Even though they admit that they don’t actually love each other in that way, and see each other as more like siblings, it is still a romantic moment until they make that decision.
Anna’s Expenses
Not every romantic gesture on the show is all about trying to end up sleeping with someone and this is a key part of that. Anna is Don’s first wife, whose name he takes from her husband who dies in the war, and he has a deep love for her which is arguably bigger than any other woman he meets on the show.
To prove how much he loves her, Don pays for her home and all her expenses throughout her life. It might not be something he does because he wants to sleep with her, unlike other grand moments, but it is certainly a huge thing to do that does come from a place of love.
Date Night In Disneyland
Don Draper certainly knew what he was doing with this romantic gesture, didn’t he? Taking Megan to California to spend time with his family all with the aim of wooing her. Knowing full well he was attracted to her, Don asked Megan to join them to help ’look after the children.'
However, in reality, the entire purpose was really for him to make a move. When the kids were finally asleep, Don swept in on the balcony of their hotel, overlooking the California night skies. It’s not a bad way to make a romantic gesture if you can afford it.
