Marry Me, Martha! Roger Sterling and Joan Holloway’s Mad Men-Inspired Wedding

This is not a spoiler alert. We have no insider knowledge that Roger and Joan will be tying the knot after over a decade of on-again, off-again in the upcoming final season of Mad Men, which returns to AMC on April 5. We just feel in our hearts that they should.

Yes, both of them are flawed (who among us isn’t?). And they haven’t always treated each other as we would have liked. But they love each other, damn it! They have a child together. And at this moment in (fictional) time, both of them are divorced and available. Make it official already. After all, it’s almost 1970! 

That said, running an ad agency isn’t easy (well, unless you’re Roger, who doesn’t seem to work very much). Also time-consuming? Staying on top of all those alimony checks (for him) and raising a young son (for her). Plus, these are two great-looking people who put a lot of effort into their personal appearance—you just don’t roll out of bed looking like a silver fox or a redheaded vixen. In case the daunting (but delightful) task of planning a wedding is what has kept them from getting hitched, we’ve decided to offer their big day, our way. This is your wedding, Roger and Joan! You’re welcome.

Chic? Celebratory? And within walking distance of Sterling Cooper & Partners? The Four Seasons restaurant checks all of those boxes. Joan loves the modern architecture, Roger is crazy about the Picasso tapestry (did you know Roger and Pablo once picked up girls together back when Roger lived in Paris in his youth?), and its midtown locale makes it easy for guests to stumble home or grab a cab after they’ve overindulged. Which they will.

In keeping with the Four Seasons’ modern but gilded interiors, and as a nod to Roger’s last name, Sterling, they’ve decided on a metallic color scheme of gold and silver. And, of course, each of these shades go beautifully with Joan’s coppery hair.

When we last left our friends, it was 1969. Which means that virtually any bride who got married over the next five or so years wore an empire waist gown. That’s great if you want to conceal a growing baby bump, but not ideal for someone with Joan’s ample endowments. She needs significantly more support, plus a fair amount of sultriness. The solution for a Joan-type? Amsale’s Rhea silk-mesh halter gown. Yes, the dress would have to do some serious time travel to make it back to 1969/1970. But its Marilyn-Monroe-meets-Halston cut is perfect for our Joanie, and that gold color is not only suitable for a second wedding, it’s also a stunning complement to her hair and fitting for the opulent confines of the Four Seasons. Roger will love it. 

Roger wears three-piece suits on casual Fridays. For an occasion as special as this, he’s slipping into a black tux, white shirt, and a long skinny black tie. Let Don and the other youngsters go for crazy patters and wide lapels. Roger knows what works for him, and it’s classic and slim-fitting. Plus, the sheen of a nice lapel sets off his hair to great advantage.

Joan considered asking Bob Benson to be her man of honor, but Roger was skittish about standing up next to a younger man. The natural choice for maid of honor was her childhood best friend Kate, who also volunteered to do Joan’s makeup (not that she needs any help in that department). But partway through the planning, it turned out that Kate had to attend a big Mary Kay sales conference the same weekend as the wedding (and she can’t miss it—she’s in the running for the pink convertible!). So Joan asked her closest friend in the city: Peggy Olson. Peggy obliged to stand up with her and grudgingly agreed to wear anything Joan chose—a red plunging neckline Lazaro number, naturally (which time traveled back to the past along with Joan’s Amsale). As his only honor attendant, Roger chose Joan’s son (who are we kidding, it’s his son, too), Kevin.

While the Four Seasons will be decorated in its signature flowering cherry blossom branches, Joan will carry a bouquet of yellow tulips—the blossoms Roger sends her on behalf of Kevin every Valentine’s Day. 

Roger’s boutonniere will be a single gardenia because it reminds him of Joan’s perfume. He knows they fade quickly and has a few extras on ice in the Four Seasons fridge. Because he’s Roger Sterling. And he’s good like that.

Don became ordained to perform the ceremony, which will consist of an exchange of the traditional wedding vows and a moving tribute written by Don, who feels that Joan and Roger marrying gives him faith that there truly is someone out there for everyone, and hope that after a few false starts, we’ll all have the chance to get it right in the end. Roger’s daughter, Margaret, will return from her cult to give a reading, a selection from The Prophet by Kahlil Gibran. Because it’s 1969 and everyone who gets married has a reading from The Prophet.

In the year in which “Proud Mary” and “Honky Tonk Woman” are released, Roger and Joan choose to go old school, hiring a band and dancing their first spin to Edith Piaf’s “La Vie en Rose,” which Joan sometimes plays and sings for Roger on her accordion.

Roger and Joan will slice into a strawberry cake covered in white Swiss meringue buttercream and sprinkled with silver sanding sugar (which is also used to rim their Champagne coupes). The cake is topped with sparklers, a fitting tribute to these two firecrackers. 

When Roger lived in Paris, he started collecting vintage sterling cigarette cases, which he picked up at the flea market for a song. It was Joan’s idea to give one to each of their 35 guests, with a handwritten note inside thanking them for coming. Truth be told, now that she and Kevin are moving in with Roger, she thinks it’s time for him to declutter. And also, maybe, to cut down on his smoking. She’s starting to think Don was on to something when he broke with Big Tobacco. And she wants Roger to be around for a good long time to come.

Joan has always said she doesn’t like French food. But Roger swears he can change her mind. He’s planned a month in France, starting with a week in Paris, then a tour of the Côte d’Azur. He wants to show Joan the France he fell in love with as a young man. And Joan, who speaks (and sings) the language is excited to finally see the country. Roger has even arranged a lunch with the recently resigned French President Charles de Gaulle, an old friend of his dad’s, telling him his new wife is a cross between Jackie and Marilyn.