John Mayer DM'd Me, We Are Now Friends, And I'm Going To Blow It

Kevin Mazur. Getty Images.

Being friends with famous people is a delicate dance. 

The more famous they are, the more carefully you must choose your words, time your responses, resist the urge to compliment them, resist the urge to book a restaurant reservation for the two of you, resist the urge to send them pictures of yourself with your wife on honeymoon to show that you're normal and grounded and won't show up at their next six live shows expecting backstage passes and, upon finding none under your name, plot to intercept them between the venue and their tour bus to beg forgiveness for overstepping, promising to play it cooler going forward, tearfully asking if we can just go back to the way things were, I'll be better, I get it now, I understand the boundaries, only to watch them board the bus, knowing it's over, except they can't leave because you stabbed all 16 tires of the bus with a switchblade during the encore in case it played out this way. 

Etc. 

Simple guidelines like those can help keep a budding friendship with a celebrity on the rails. 

Take, for example, my friendship with seven-time Grammy winner John Mayer. Let's look at that pic for a moment. Perfectly in his element at some musky bartop worn smooth from a decade of elbows leaning in for another round, sipping a Bud Light, tugging pensively at his mustache in a t-shirt with a look that says "saddle up, amigo." 

Except we didn't ask if we could sit next to him. Who would? Who would dare ask seven-time Grammy winner/tastemaker/sex symbol/generational talent John Mayer "is this seat taken?" 

Me, guys. I'd have to. Because according to John Mayer, he and I are friends. 

Here's how it started. Recently, I conveyed the travel hack of sneaking free food from a Delta Sky Lounge onto your flight on our podcast, Oops:

John, as I call him, saw this clip. It tickled him. So he hit me:

Thank goodness I was asleep. It would be tough to nod off after reading an out-of-the-blue DM from John fuckin' Mayer. As it were, being unconscious meant it took me five hours to respond. If I know John as well as I think I do, that's about five hours longer than anyone has ever taken to reply to him. 

Who the hell is this guy? It's been five hours. Jesus Christ, he's probably blowing rails with Sarah Bareilles and Chad Ochocinco or something. - John's brain 

When I woke, I saw the DM and obviously thought I was still asleep. But then I rolled over and saw my wife, which shook me back to my tragic hetero-reality, which is my fault even though it's not a choice. Still, a boy can dream with his eyes wide. 

I replied:

Now, we both know John would sooner find himself charging $25 for happy birthday Cameos than in a commercial airport lounge. But another rule of being friends with celebs is to treat them like normal people. "John Mayer? Super down to earth. Last time we hung out, we just went for a walk around the reservoir. His idea. I had a dinner rez but he said he was tired of spending money with the holidays coming up." - me in two weeks. You get the idea. 

Now, I figured that would be the end of the exchange. Boy was I wrong. 

He responded:

Cheeky. Humor so dry it makes you crave a Gatorade bath. But of course he's got great jokes. Guy tours with Chappelle, for God's sake:

Lester Cohen. Getty Images.

Can't wait to get him on stage with me. Crowd will love us. 

I set a timer for 2.5 hours and then responded carefully:

Continuing the game here, I cast a lure filled with relatable credit card woes, playful aphorisms, and a self-deprecating cherry on top. OF COURSE John Mayer isn't pissed that Delta raised their MQD requirement for Diamond Medallion status from $15,000 to $20,000 for 2023. OF COURSE he's not stowing rice pilaf in to-go cups or trying to "get back" at the big credit card/airline union. Why not? He finally tells us: 

He flies private! Of course he does!!! You don't win seven Grammies, stare down 20 million albums sold worldwide, top the charts, date the greats, tour with the Grateful Dead, and get named to Time's 100 Most Influential People only to exceed bag limits at LAX, face delays at O'hare or wash your hands with prison soap at La Guardia. 

You fly private, leaving upon your arrival, flying at 45,000 feet, texting your assistant to plant six acres of pine trees to offset your carbon footprint because you're a good and decent man. Hot towels galore. Sit in the cockpit with a headset for landing. Drive off the tarmac in an Escalade with windows so tinted you wish they made sunglasses out of 'em. 

He didn't have to say it, but I liked that he did. And it made me think he liked that I pretended not to know. That I didn't lay down a red carpet for him or ask for a picture. I was just being a guy to a guy, dude to dude. It's that same down-to-earthness which made Julia Roberts fall for Hugh Grant in Notting Hill. John Mayer's just a guy, sliding into another guy's DMs, asking him to shoot the shit. 

I obliged:

To which he both hearted my message, and immediately replied…

And there you have it—my masterclass: How to become friends with famous people.

I can't wait to give him a hug. 

PS- if you're actually wondering how to avoid blowing a budding friendship with an A-list celebrity, do NOT write a 1,000-word neurotic elucidation on that friendship and post it to one of the internet's most-visible websites. 

PPS- John, if you're reading this, I've got a rez for us at 4 Charles Prime Rib next Wednesday evening.