Why Is Kiernan Shipka Hanging Out With John Mayer?

Over the weekend, 45-year-old John Mayer was spotted out in Los Angeles with 22-year-old Kiernan Shipka. No, it wasn’t the father-daughter square dance. No, it wasn’t a last-minute Get Out The Vote effort featuring celebs who rose to fame in the early aughts. Unfortunately, it seems like it was a date.

Perhaps it could have been a four-hour platonic meal at Santa Monica’s Giorgio Baldi, where Mayer serenaded Shipka, but the Daily Mail claims that the two got into separate decoy cars after the meal only to pull over a block later so Shipka could hop into Mayer’s limo. So put the suitcase on the bed—there’s a lot to unpack.

This isn’t the first time the Mad Men star and “white supremacist” dick-haver have been spotted together. In February, dating rumors bubbled up after they were spotted hugging outside of LA’s Tower Bar. To be fair, I’ve hugged my uncles outside of restaurants, but those restaurants aren’t paparazzi hot spots where celebrities go explicitly to be seen. This led fans to ask Deux Moi, the Instagram gossipmonger, if Shipka and her alleged boyfriend, filmmaker Christian Coppola, were in an open relationship. Yes, the Coppola in question is a Coppola, but we can’t go down the nepotism rabbit hole. (Also, it isn’t totally clear what their status is. Friends? Lovers? Exes who go to public events together?) We need to focus on Hollywood’s other indulgence: age-gap relationships.

The age gap between Mayer and Shipka is old enough to legally order an espresso martini and have voted in the 2020 election. But I need to quickly address the fact that they got into separate cars only to meet back up a block later in Mayer’s limo. The bait and switch. The secrecy. A limousine. It all feels very Old Hollywood. Older than Mayer, even. Are celebrities still traveling around in limos? I am both terrified of and fascinated with the image Mayer has concocted of himself: a Gen X Lothario serenading young women with Grateful Dead music their dad probably listens to.

This isn’t the first May-December romance for the man who sang, “Twice as much ain’t twice as good.” Over a decade ago, when Mayer was 32, he dated then-19-year-old Taylor Swift. Swift has written about regretting that relationship in a number of her songs, including “Dear John,” “The Story of Us,” and, most recently, “Would’ve, Could’ve, Should’ve.” Another of Mayer’s many exes, Jessica Simpson (who was, at least, closer to his age when they dated and whom he once described as “sexual napalm”), called their relationship “unhealthy” and “manipulative.”

In September, Shipka also sparked dating rumors with 42-year-old BJ Novak after being seen out to dinner with him a number of times. If you are a reader in the Los Angeles area between the ages of 21 and 28, I am begging you to find Shipka and show her that going to brunch with people her age is miles more fun than pasta bolognese with these dudes.

Of course, Shipka really might just be going out to dinner with Mayer and Novak for non-romantic reasons. Maybe she needs an older brother-like figure to give her tax advice. Maybe they’re describing the appeal of Alice In Chains. Or perhaps Shipka is explaining to these Gen Xers what “sus” means. Obviously, the rumors she’s dating either of them have ignited feelings for lots of folks, myself included. Despite Twitter crumbling from Musk’s takeover, users are still managing to log on and demand that Mayer “stay away from her.”

Obviously, she’s grown up, but for many, Shipka is cemented in our minds as Mad Men’s 7-year-old Sally Draper. Similarly, Mayer is the man who got famous for writing about running through the halls of his high school in 1998, a year before Shipka was born. Until anything is confirmed, I am personally going to stick with the older brother tax advice theory, because financial law and 23-year age gaps are both complete mysteries that do not appeal to me.