Lost Weekend in Jed Square

Written By Jed Heneberry

“Crying in a suit and tie, but you should see the other guy.” —Phoebe Bridgers, “The Outside”

If any of you out there are concerned for the man you saw crying last Tuesday on the streets of Harvard Square, please don’t worry—I was just listening to Phoebe Bridgers’ new album Lost Weekend.

“Lost boys never grow up, never get old. Lost boys find me.” —”Lost Boys”

Well, I wasn’t just listening, I was also doing a whole lot of remembering.

“This is gonna kill me … wait.” —”Kill Me”

Since it came out in mid-August this album has levelled me again and again, sometimes without warning on a regular old Wednesday, so I was pretty sure I knew what was coming when I dared play it in a special place where my band would busk during high school summers.

“Being myself wasn’t easy … Do it for me.” —”The Governor’s Waltz”

I found out Harvard didn’t accept me in front of my math class in the A-wing of Dedham High School in 2002, which was embarrassing, but also not the worst news I received in the A-wing that year.

“Now I don’t know if I can make it tonight, but what are you doing the rest of my life?” —”Bobby”

This particular Tuesday here in 2026 Kelly and I had spent a lovely day pretending to be on a college date, which theoretically would have been possible a few decades earlier if the basketball team could have matched Kel’s scholarship, and if the school had wanted me, and after reconnecting to this spot I was all wired up and walking around solo with the album in my headphones.

“Back when no one could tell us apart and I turned down the music to parallel park we were playing for no one on top of the world.” —”Lost Weekend”

In the early 2000’s Bob, Brendan, and I were Three From Perfect, and all summer we’d haul drums, guitars, amps, power inverters, and boat batteries into Harvard Square, unload it all in the midst of psychos in traffic, then play a show on a street corner and put out a guitar case to collect tips—I was invincible, on top of the world, and ready for my bright future.

“I’m gonna put myself together. You can go or you can stay. I’m gonna put myself together either way.” —”Haunted”

At some point in the spring of 2002 I had the last conversation I’d ever have with my dad, not in Harvard Square but not far away in Dorchester, and it sounded pretty much exactly like this lyric, and at the time I’d felt pretty great about it, but over the years I’ve felt a whole lot of different, complicated ways, and all of them seemed like they were coming at me here in 2026.

“If you’re drinking, then I’m drinking.” —”Panorama”

Earlier in the night on our psuedo-college date we’d done a very Boston thing and met my friend Sully for a couple beers (no beers) curry at Aatma @ Widowmaker Brewing, Sully and I previously having met in 2nd grade at the school where his daughter is now in 5th, so my sense of time and space had already been sufficiently warped.

“You’re back to the ocean burning red and I can’t imagine you dead, but you are every day.”—”Still Standing”

I haven’t mentioned that part of the reason Phoebe can perform emotional open-heart surgery on me even if I’m walking around a bunch of college kids in suits is because this album is in part about the recent death of her dad, and it feels to me a lot like how I feel about the not-as-recent death of mine.

“Not getting any younger honey, but if we don’t try how can we be sure?” "—”Liberty Tree”

Walking in the footsteps of 17-year-old me gave a familiar visual perspective that threw all of life’s other changes into stark relief.

“Never going back again the way it used to be is not the way that it is.” —”Never Going Back!”

And on this long walk and listening session, bouncing back and forth between past and present, laughter and tears, I enjoyed the perfect music at the perfect time, one of the best flavors of moment you can have in life, I think.

“I don’t know why I’m crying until we’re dead or die trying.” —”I Can’t Wait”

I did know why I was crying, and I was good with it.

“Started watching a movie, one where they go back in time, and it got to me, I don’t know why.” —”As Above”

What got to me, in the end, in that spot where I felt invincible and also where Jem interrupted Dougie’s and Claire’s date that one time, is that 17-year-old me wasn’t wrong at all to feel invincible because great things did happen to me, and because I’m still standing through all the tough ones, and that it is always OK to cry, and also to feel excited and confident and optimistic even knowing tough things will happen alongside the great ones.

“I am my old man’s oldest son. I fought the wall and the wall won. But if I ever come out of hiding, you won’t have to know how to find me again.” —”Lost Weekend (Reprise)”

When my emotions are in hiding it’s no good for me, and somehow Phoebe Bridgers writes and sings things that help me see, even if it’s through some tears, and because she’s shared so much with me, I wanted to share a little of myself with you, so thank you Phoebe and thank you too.

If Harvard ever needs a Professor of Long Walks & Deep Breaths, I’d be happy to put them on my waitlist. jed@kindandfunny.com

At the Movies

The movie theater is a happy place where we refill our creativity (and do a lot of our creative work). Here are this week’s highlights:

  • Coyote vs. Acme is really funny. Will Forte & the Coyote from Looney Tunes are an incredible comedic duo, and there’s a ton of creative thinking on display. We very much liked it.

  • Tony, about a young Anthony Bourdain in Provincetown, was interesting, and it has Antonio Banderas in it.

Book Talk

Reading is one of the best things we can do for our human brains. Don’t let those evil robots win!

  • Vigil by George Saunders

    • I love book people, and I say that because this book was recommended to me by a woman in a bagel shop because she saw that I was holding a copy of Trevor Noah’s Born a Crime and she introduced herself saying, “I am reading mainly books about death these days because it is all around me, and it is closer to us than we think.” With that intro we hit it off, and she recommended to me this brief and beautiful meditation on death and regret while I recommended to her the exceptional 4,000 Weeks: Time Management for Mortals by Oliver Burkeman.

  • Cosmos by Carl Sagan & Orbital by Samantha Harvey

    • This was a lovely duo, one a classic outlining our studies of our place in the universe and the other a contemporary reflection set on the International Space Station that helped me feel all of the things to feel when gazing up at the stars and considering how little we can know of where and when we find ourselves.

Client Highlights

Kind & Funny clients are the coolest people around. Here are some of the great things they’re up to:

Jed Heneberry
Next

Gold Days from the BirdFair