Tour Diary No. 1

Wednesday, August 12
I wake up early to eat breakfast and have a telehealth appointment with one of my specialty doctors. The extension I got to stay on my parents' health insurance til age 29 expires soon, so she tells me I need to figure that out ASAP. I spend my last few minutes before departing for the airport on the phone with a health insurance broker, who ends up leaving me on hold too long so I have to hang up so Holden and I can catch our ride to LAX. On the way, a woman slams on her brakes ahead of a crosswalk, narrowly missing a collision with a pedestrian. He slams on the hood of her car, and she gets out to scream at him and threaten calling the police. While our driver peels away, I think about how this interaction is basically what it feels like to be on social media, every minute of every day. I navigate security--peerlessly, as always--and our flight takes off exactly on time, a modern miracle. One of my seat mates enters our row with the announcement “make way for the Sasquatch!” which is crazy because he is a normal sized man. The woman behind me has her feet on my arm rest, an experience I chronicled in a handwritten poem that I shared here already. It’s about an hour in the car from Logan to the Portsmouth Holiday Inn. The hotel is in some degree of disrepair because it is under construction, but it’s okay because this is the first thing we see when we step inside:

I elected not to eat at our food stop on the way, because the only options were Jersey Mike’s (one of my favorites, but I’ve been avoiding it due to the cyclospora outbreak and the inevitable cross-contamination of shredded lettuce on cutting boards) or Wendy’s (earlier that day I’d seen a TikTok about a beef recall?) or Raising Cane’s (no real objection other than that I haven’t had fried chicken in years and I want my first time back to have some more fanfare). Instead I order a plain cheese pizza from One Of The Delivery Apps and eat it while FaceTiming with my parents. They are meeting us at our last show in Massachusetts, but right now they are vacationing in Montreal, a place my father loves mainly because it is the geographically closest point he can go to flex how well he speaks French to native speakers. They are giggling and eating room service together. I am anxious and tired from the long travel day so I am mechanically eating the pizza, almost in a fugue state, until I realize I ate almost the entire thing. I put the nearly-empty box on top of a high cabinet to block this fact from my mind. I talk to my boyfriend for a while but he is the hardest working man I have ever met doing a million side projects and it is getting late on the east coast, so we part ways after I crack us both up sending him a million pictures of vets doing dentistry on huge zoo animals. He keeps a running list of the funny things we say on the phone, so this is our most recent entry:

Him: Did you know that AOC is freezing her eggs?
Me: Yes. Did you know that horses have continuously erupting teeth to compensate for the constant wear from grazing?

Thursday August 13
I sleep in absurdly late, then coax myself out of bed because I forgot to bring a raincoat and it is definitely going to rain at some point during this east coast summer week. I get a rideshare to what I think is a Target, but is actually just some random town square, so I have to get another one. While I wait for it, I get a decaf iced latte from a place called Elephantine Bakery. Somehow the timing works out perfectly, my latte arriving as soon as the car pulls up, but it was close, and I could tell the baristas were eyeing my big city impatience with disdain. I get to Target and decide to also pick up a cheap hair straightener and heat protecting spray, because I have never really known how to do my own hair but I get frustrated looking back at photos of myself from shows when I have potentially avoidable frizz. I know I won’t use it for the show tonight, or tomorrow night, but maybe the other two? I also buy a ton of protein bars, because whenever I talk myself out of eating whatever restaurants are available (either due to the lack of nutritional value or because I’ve convinced myself it’s going to poison me), I can rely on Barebells and Built Puff Bars to satiate me. Girls, if you’re listening, send me more! I trust you with my life.

When we arrive at the venue, everyone does their usual routine of Wandering and Exploring. Holden does his usual, which is Unbelievable Ability To Nap:

During soundcheck, we all work out the usual first-day kinks and jitters and are pleased with how booming and clear our sound is. The only issue is that we have sporadic dropouts in our in-ears, but we know it will be resolved by the show. Kristen helps me put my strap on a guitar she’s letting me borrow for this run, which eventually also requires assists from Will and Holden to press a metal thing through a hole or something, I don’t know, these instrumentalists are a wonder to me and I would be nothing without them <3 Holden and I eventually go to catering, because when you’re on an arena tour there is free food for everyone, and while in previous years I was unable to partake because of my Million Dietary Restrictions, now I can eat whatever I want. I eat chicken piccata and roasted red potatoes and half a slice of chocolate cake. The cake is so darkly cocoa-y and plasticky sweet that it immediately makes me nostalgic for literally any birthday party I attended as a child, the flavor of chlorine in someone else’s pool, or the cold dry air of a second grade classroom. I also drink part of a Diet Pepsi from the catering fridge but I’m not really a Pepsi girl like that so I don’t bother finishing it.

Our set was incredibly fun, because it is incredibly fun to play your original music in a big beautiful room while opening for one of your heroes, even when the sound drops out of your ears two or three times on every song. We are all laughing about it because if you’ve been touring long enough, you know that the odds of having a show day where literally nothing goes wrong is basically zero. Brandi stops and says hi to me after our set, looking beautiful and shiny in a big sparkly blazer, and tells me we’ll have to sing together on the other dates, to which I eagerly agree.

Tomorrow we have an early wake-up, and theoretically we have to stay at the venue til pretty late for merch count…but I somehow manage to find a driver who will take me from Maine to New Hampshire without making me feel like an idiot1 so before I know it I am back in my room, calling my parents again and wiping my makeup off. I shower, text my most online friends about my epiphany that Shawn Mendes is yassified Clavicular, and go to sleep (but not before accidentally seeing a horrifying TikTok about one of the darkest criminal cases I have ever heard of in my life. Stop scrolling before bed it does nothing for you!)

Friday August 14
Early wakeup so we can drive to the second show in Connecticut. Before we leave New Hampshire we pick up breakfast from a diner near the hotel. It has an awesome neon sign, pictured here:

I get eggs and potatoes and wheat toast and an orange juice. The orange juice is clearly fresh so it’s really good. The eggs are pretty dark brown which to me is actually a comfort because at least I know for sure they were cooked all the way through. The toast is also really dark brown which is also a comfort because it reminds me of my father and my grandfather, both of whom used to burn toast for me on the rare occasions I would ask them to make it. We stop at a gas station as well, where I purchase the cannibalistic Oreos that contain cookies and cream filling. Last time I bought them on tour I convinced everyone to share them with me but no one seems interested so I eat one and put the rest in my bag. On the drive to Connecticut I listen to the new Phoebe album, which is a masterclass in making every single word count (so many of these songs have so few lyrics and yet every single one of them is excellent). I need to listen to it again and again though. I don’t have a favorite yet.

We have to arrive incredibly early to Mohegan Sun because of some merch-related reason so we have a lot of time to kill. I finish Strange Girls by Sarvat Hasin and rate it a 3.5/5 on Storygraph. I experienced above-average enjoyment of the book, and there were some really beautiful passages, but there were parts I found a little slow. My favorite part was an extended second-person meditation on the secret, almost perverse desire for fame that hides inside most (if not all) authors, and creative types more broadly. I would have loved to see more of that! I also really liked the chapters in first person from Ava’s perspective; I wish the alternate chapters would have also been first person, but from Aliya’s.

Holden wants to explore the casino (where the Basketball Hall of Fame Induction Ceremony is apparently also happening), and I tell him that while he is shopping for a belt I would like him get me a big sweatshirt of any kind because it’s so cold in the green room. He returns with something WNBA-related for me, NBA-related for himself, and no belt because he forgot.

After soundcheck - no dropouts! - I rehearse “God Has A Hitman” with Brandi in her green room. Though she graciously lent her voice to the record, this is our first time singing it in the same place. I sweat through my Reformation x Camille Rowe lace top while harmonizing with one of our greatest living singer-songwriters and she keeps being so nice and telling me how great I sound and I feel overwhelmed and, even though I generally take great umbrage with the very idea of impostor syndrome because it always sounds like humble bragging to me, I have to face it: I feel impostor syndrome. It’s the feeling I got when I first stepped onto an arena stage opening for Noah Kahan, and again when I arrived on set to shoot my first ever film role opposite Denzel Washington under the direction of Spike Lee (these two things happened in the span of a month), and again a year later when I found myself in Justin Bieber’s backyard having a jam session with him and his buddies--what am I doing here? How the hell did this happen? Somehow, even though these are all things that I’ve been obsessively manifesting and working toward since I was a child, I don’t understand how I got them. And then inevitably life goes quiet for a few weeks or months and I feel like surely something else needs to be happening…and then the cycle begins again. Anyway, our set sounded great and Brandi sounded great and it all went by in a blur.

Holden and I explore the casino a little bit after the show. I accidentally dropped my eyeliner on the bathroom floor, and I had to get rid of my bronzer and concealer awhile ago after accidentally leaving them in the overheating van trailer, so he takes me into the truly awe-inspiring casino mall to shop. It is very hard for me not to buy sooooo much makeup when I am presented with the opportunity to do so but I stick to my guns. We walk around some more. Holden finally gets a belt. He shows me the Italian restaurant with the fake waterfall on a fake rock wall. I've never been to Vegas, but I assume this kind of Gilded Age artifice is all the rage there, too. We return to the green room. Kristen helps me navigate my way out of the labyrinthine casino exits and politely points out that my shoe is untied. Little does she know that my previous guitarist (Kevin <3) has been driven to genuine madness over my refusal to tie my shoes.

When I get to my hotel room, all earlier notions of impostor syndrome are stripped away. It’s dark and seemingly haunted and covered in wall-to-wall carpet (my great nemesis) and it smells like mildew. Tour does not become glamorous until you’re headlining rooms at least twice the size of the rooms I headline, so we’ve got a ways to go. For now, I fight with my shower and try not to look at the stains on the recliner and manifest a version of me who is five years older, headlining an arena tour of my own, falling asleep in a room that smells like eucalyptus, or nothing at all. I eat my second protein bar of the day and notice that my cannibal Oreos have shattered in my plastic bag. I also call my parents again. They tell me how proud they are of me.

Saturday August 15
We stop at Panera on our way to New York. Leigh Ann and I remark on the solid, predictable comfort of chain restaurant food while we sweat through our sandwiches. We make one more stop for gas. I see a 9/11 Never Forget sign in the minimart which I take to mean we've arrived in New York state. I purchase snap pea crisps for the first time in my life. Holden talks me out of buying protein chips made of real chicken and egg whites on the grounds of likely potential stomachache. I eat the snap pea crisps and they are so good and such a salve during this time of culinary and agricultural uncertainty. Our hotel here is so much cleaner than the one we had in Connecticut, and we will be here for two nights. In the lobby there is a baby playing with a balloon. His laughter ricochets and fills the room. Will and Kristen make plans to get haircuts together somewhere in town. I remember the straightener and heat protectant in my suitcase.

While I’m in my hotel, I work on a feature. I had the idea for this script ages ago, but experienced a renewed enthusiasm for it when I realized who I want to play the two leads (and they’re both people I’m internet friends with). My plan right now is to finish the screenplay as soon as possible, get notes on it from my friends and family, and then send it directly to the people I’m envisioning in the cast. They’re both wildly successful and certainly too busy to do anything with it right now, but I know I would be flattered if someone sent me a script they wrote about two best friends and said, I wrote this with you and your best friend in mind. So that’s good enough for me. I also order food from a make-your-own-protein-slop-plate place. I eat bland rice and chicken and sweet potatoes because I have gotten so few real nutrients on this trip, but I eventually I give up on them because it is a level of blandness that I cannot abide.

My boyfriend and I talk on the phone for a while, because he’s still working but it’s a Saturday afternoon. He talks me through what he’s stressed about and we decide to parallel play, aka work on our separate computers while FaceTiming on mute. It’s getting late for me, but even though it’s also 9pm in LA he’s just getting started. I do what I often do when he’s overwhelmed, which is to send him a treat. He gets a link to schedule a prepaid order of Levain cookies, and he tries to protest but it’s too late, it’s already paid for. After I hang up and shower, I find myself excessively anxious, so I try to do a guided meditation while I fall asleep, but it doesn’t really help so I have to turn it off.

Sunday August 16
I wake up an hour before my alarm because I’m having a nightmare. In it I’m out with Kevin and Holden in London—plausible—and a strange man starts following us, and Kevin notices first. He grabs my guitar and starts running, so Holden and I follow suit, and then somehow in the dream Kevin is able to carry me as well. He gets us to safety, slamming the door behind us in a random restaurant that for some reason can keep this man out. I text Kevin’s wife Alyssa—your future children will be safe lmao—and explain what happened. Then, for reasons again unknown to me, I find myself in a clothing store—I think in the adjoining building—where I weep to the sales associate about what is happening to me. It is nighttime, so the store is closed, but she lets me stay in there anyway. The dream then grows more sinister—the original stalker appears at the window, so I hide, and then the sales associate leaves to give a statement to the police, but when she returns she is also a danger to me. At every stage I experience the dream dead giveaway of trying to scream but no sound comes out, but it’s only at this last plot twist that I finally wake up. I manage to go back to sleep and get that last hour.

We stop at a bagel place with a Comic Sans sign on our way to Bethel Woods:

Unsurprisingly, the bagel is excellent, as New York bagels tend to be. We arrive at the venue with basically everyone in the van talking about Lyme disease and ticks, which for someone with OCD (me) is real-time full-throttle exposure therapy. I already know I will be spending as little time outside as possible, and that I will be lathering myself in bug spray when we have to go onstage. I read some articles about the origins of peanut allergies, then I talk to my boyfriend on the phone while Holden plays Toontown. During soundcheck, we encounter this little number side stage:

Caity arrives because she’s taking photos of the New York and Massachusetts photos. It always feels like play when she’s around on show days because we’ve been friends for way longer than I’ve been touring. It’s raining, but the stage is covered, and it’s all indoors going there from the green room. During our pre-show downtime, I finish the first draft of my feature. It’s only 87 pages, so I know it has a lot of room to expand and change, but I’m excited to have the first iteration of it committed to (digital) paper. I really have no greater mood-booster than to finish a draft of a long-form project—a feature film, a novel, an album. Nothing makes me feel more wholly like me than to finish something I’ve been working on for months.

My mix feels extra clear and crisp in my ears, and I can’t stop smiling while we’re playing. I attribute the heightened joy and confidence to the high of finishing the draft. Like the other nights, there are only a few scattered Jensenheads in the crowd, but it doesn’t matter, because the band sounds great and playing for 45 minutes feels like flying after over a year of playing headline shows that are almost twice as long. When we finish our set, Caity and I go back to the green room to take portraits.

It’s still raining when we leave, and it’s late when we get back to the hotel. I wipe my makeup off and brush my teeth while my boyfriend tells me the insane story of his night picking up something from a crazy guy on Facebook marketplace. We hang up and I get into bed. Holden texts me that he needs a protein bar. I tell him to come to my room and offer him two options. He’s sweaty from a late night workout. I send him to his room and feel my heart twist and tighten. He’s not going to be on the fall run because he got another tour. It’s an amazing opportunity, a far more prestigious job than this one, and never would I stop him from taking it. But I already miss him even when he’s standing in front of me. More than being a writer or a musician, I was born to be his big sister. I love taking care of him. I am afraid of most people--afraid of their judgments, their assumptions, the way they say things they don’t always mean and that I don’t always understand. But Holden is one of the few people I’m not afraid of. Since he was born it’s been me and him and the rest of our wacky family against the world. And a few people have joined the team since then, but nobody gets it like we do. Nobody, especially, gets me like him.

Monday August 17
We get a late checkout so we hit the road at noon, stopping at a place nearby called Mister Croissant. I debate whether or not to get something, as since the pizza incident I’ve been trying to eat as healthy as possible, then realize that coming across an establishment called Mister Croissant is a once-in-a-lifetime opportunity and I get an almond one. It’s really good and I eat the whole thing. Caity and I try to go to a bookstore across the street, but it’s closed on Mondays. On our car ride, I finish the second of two books that I brought on this trip—My Nemesis by Charmaine Craig. The language is masterful, and the premise is totally up my alley—a bunch of academics all having emotional affairs with each other—but something about it doesn’t grip me as much as I want it to. Still, I commit to finishing it before the car ride is over. Now I am out of books. I only brought two.

We arrive at our hotel in the Berkshires and it is truly the middle of NOWHERE. We wait for a while for Leigh Ann to come back to the van with room keys and I feel like a pilgrim without cell reception. Naturally, everyone’s rooms are ready but Leigh Ann and Jon’s, and mine. We drop everyone else off—this hotel is basically a bunch of clusters of cabins—and then wait. I manage to connect to the hotel Wi-Fi while sitting in the parking lot, and when I finally get to my room I am astonished at its size. It’s two stories, with a full sitting room, two closets, and two bathrooms. The decor is drab and depressing, but it’s mostly clean, and you can’t argue with the square footage. I get on the phone with a health insurance company and am frustrated for an hour and a half before eventually calling my mom and figuring it out with her while I navigate the website. My coverage formally ends at the end of September, so I apply for a plan that will start at the beginning of October. I don’t know when I’ll hear back from them, but the headache is temporarily over. I order a bunch of snacks from a grocery store and it takes over an hour to get to me because as I said we are in the middle of nowhere. It arrives, miraculously, without incident, and I eat crackers and hummus and edamame and drink orange juice while I scroll on my phone. Holden calls me—he decided to venture out into the town despite the unreliability of ride shares in this part of the state—and he informs me that the restaurant he’d scoped out the day before was even better than anticipated, and he’s bringing me a chocolate chip cookie. (And someone on the restaurant staff knew who I was by my “cute little glasses.” Incredible news). He appears at my door with the cookie an hour later, then wanders off to explore the basketball court. I lose track of time separating my unpublished manuscript out into chapters so I’ll have an easier time posting them on Substack in the coming weeks. When all is said and done, I have 38 chapters in total, 5 of which I’ve already published, so I’ll finish sharing the full thing the first week of April. Exciting! If you’ve read this tour diary this far, I would recommend you purchase a paid subscription to this Substack, it will be worth it for you.

I realize I left my phone charger at the last hotel, and also that my power bank refuses to charge itself. This presents an issue. I schedule a ride to Tanglewood for tomorrow—Leigh Ann got me a later checkout than the band—and also a breakfast order for the morning. I plug my phone into the charging bank and hope it’ll tide me over until I get to the venue. I shower and brush my teeth and use my computer, which I blessedly still have a charger for. My mom already read my feature and gave me some notes, so I write an additional scene for it and then go to sleep.

Tuesday August 18
Somehow it’s the last day. Our flight tomorrow isn’t until late morning, but we have to drive back to Boston by 8am which means our van call is 5am which I really can’t be thinking about right now. My boyfriend’s parents are coming to the show tonight, which means I’ll be more nervous than I normally am. He’s seen me perform a couple times, but they never have. The band doesn’t understand why I’m so nervous if they already like me, and maybe it really is irrational, but to me it makes perfect sense. Anyway, my food takes longer than it’s supposed to in the morning, and I try to order a bunch of chargers and cables but the delivery app just keeps showing me that the order was received and no one is shopping for it and I’m running out of time so I give up. Hopefully my driver will have a charger, or at least I’ll get to the venue without incident and someone else can help me charge my phone.

Not only does my driver have a charger, but he is the absolute GOAT. To be fair, I’ve only had excellent ride share drivers in New England, they all seem to really enjoy doing it and are very knowledgeable about the area. This guy in particular has driven many artists to Tanglewood, so he knows exactly where to drop me off. Leigh Ann retrieves me and I drop my things in the green room. I write the second of two new scenes for the feature, then am whisked off to an obligation I forgot about: I am doing an interview with a history professor from Williams about my song, and also the material and indigenous history of Massachusetts. All this, because of a single social media post (although probably also because no other musicians radiate teacher’s pet energy quite as much as I do). Naturally I have a ball, because I love talking to professors, and I love talking about songwriting. When it’s over I am golf carted back to my green room. I change into show clothes and do my makeup so Caity can take portraits of me. We soundcheck for all the people who are already waiting on the lawn. Afterwards I eat steak and chimichurri from catering with the band, and it is determined that Brandi will come out during my set for Hitman, and also I will come out during her set--with Holden!--to sing “Dear Mr. President.” Holden and I go to Brandi’s green room to rehearse, which is very precious to me. Brandi gives me flowers and a thank you note; I remind myself to make sure my thank you note gets to her green room after the show. We return to my green room. My parents come backstage, as do my boyfriend’s parents--they all went to dinner together before the show, the first time all four of them are in the same place. I am wired from this last-minute practice with Holden and Brandi, and my mom takes pictures of me with my boyfriend’s parents so I can send them to him.

The set is wonderful--loose and relaxed and joyous. Brandi sounds incredible. It is hot as HELL under those lights, barely a breeze to speak of, and I feel my hair getting soaked in sweat. After the set, the weirdest thing in the entire world happens.

A woman knocks on my door.

“I have the governor of Massachusetts,” she says.

I think, ha, ha, what a weird thing to say. And then Maura Effing Healey walks into my green room with the First Lady of Massachusetts and also all their friends.

?!

No one told me this was happening, because no one in my touring party knew. This is just an unbelievable side quest that is happening, again, because when I was 25 I got dumped by a guy from Massachusetts and when I was 26 I wrote a bizarrely popular song about it. I AM MEETING GOVERNORS. We take photos together. I am floored. Will is a Massachusetts native and he gets a photo with her too; he is BEAMING. I still cannot comprehend how this is my life.

Holden and I wait side stage at the end of Brandi’s set so we can be ready to come out during the encore. I fist bump him, then hug him. We were just two little kids taking piano lessons. I remember coming home from college on weekends and there he was, 14, 15, 16 years old, playing my songs on the huge piano in our living room as my walk-in music. Now we do this together. I’ve said it already, but I am going to miss him so much on the fall tour. Thank God we’ve got one more festival together this summer.

Brandi gives me an incredibly generous reintroduction, and then we come back out onstage. I later find out Holden could barely hear the piano in his in-ears, but he crushed it anyway. It’s the last show and I have a week before the next one, so I really let it rip without worrying too much about technique. Brandi and I hold eye contact for much of the song, and I feel so cared for and so held. She’s such a benevolent figure in my life, the exact kind of musician I’m trying to be. It is an embarrassment of riches to know her and get to learn from her onstage. And it’s so healing to sing that particular song under these particular political circumstances with another artist who’s so unapologetic about uplifting her people, her community, in the face of such bitter hate.

The crowd is raucous. We depart the stage and all the parents come backstage to debrief and then say good night. We sit for a while in the green room to wait out the traffic, and then it’s back in the van so we can drive to Ludlow, our last stop. In the morning we’ll leave at 6am (a little extra time, blessedly, though it won't make much of a difference--as I type this it’s after midnight and we’ve got another half hour before we get to the hotel). Still, I have to shower and wipe my makeup off and brush my teeth and make sure all my bags are packed. I’ll have eight days at home to rest (although I have a side quest planned for next week that I’m excited to tell you guys about), and then I’ll hit the road for a weekend to play that festival. Then it’s another week and a half at home before fall headline…any of you comin?

If somehow you’ve read this long, I’m floored and grateful. Should I keep doing these for future tours…?