October 16th, 2025

Between St. Peter’s sunsets and San Donato soil, I learned that real abundance isn’t money — it’s alignment.

Hi besties,

Another week has passed and I’m officially in my final five weeks in Italy — screaming, crying, throwing up (and not in a good way). This past week was such a whirlwind — in the best way. American Boy returned to the United States, and before I could even process a single emotion, my bestie Rachel arrived from New York the next morning, and she came with me to San Donato — my first time back since last summer.

Here’s what you’ll find in this week’s’ diary:

• Roman Rooftops with Rachel

• Pasta-making class

• We met Captain America…

For paid subscribers 🔒

• San Donato !!!

  • Hometown Date

  • Citizenship & Family Secrets

  • The Bakery & the Blessing

  • Old Friends

  • The Real Bakery

• Dream Money, Old Identities & the Art of Becoming

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Roman Rooftops with Rachel

Rachel arrived Friday morning, fully ready to rally. She proves that jet lag is a choice. We spent the afternoon wandering (mostly bookstores, naturally) before getting dolled up for rooftop aperitivo.

I’ve been quietly grading each rooftop I visit with friends — view, vibe, service — and most have failed spectacularly. Bayleigh and I were once turned away so rudely for being twenty minutes late (running late is normale for Rome), and when the boys were here, we made it on time for our reservation but still got treated like a nuisance. They were rude and slow and I had to beg for us to be served. I literally begged for olives and aperol. The view was nice, but only visible from a small slice of the bar. Wouldn’t recommend.

But this bar? A dream. Terrazza Les Étoiles — fittingly French, since the Italian ones were letting me down. We were greeted kindly, seated at the best table on the roof, and treated to a perfect aperitivo: one cocktail, a little pre-fix menu, and the most breathtaking view of St. Peter’s dome glowing at sunset.

After, we gallivanted through Trastevere, popping into bars until eventually meeting up with some Roman friends, who warmly welcomed Rachel into their big group. A solid first night.

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Pasta Making Class

It might be a little touristy, but Rachel had an Airbnb gift card, so we booked a pasta-making class with a former Michelin-star chef named Luca. It was so fun — we made fettuccini, ravioli, and tortellini by hand. Nonna would’ve been rolling in her grave watching me take that class.

Luca humbled me immediately — mostly about my posture. The table was so low I had to hunch over, and he came by to correct me the way my mom used to. Thanks, Luca.

We ate our fettuccini with red sauce, then the tortellini (stuffed with ricotta and nutmeg) and ravioli (filled with tartufo) in a butter sauce. Delicious. But the best part came after — chocolate sausage. I was the only one who recognized it, and when Luca asked how I knew, I told him I had Italian roots.

The class was in English, but we ended up chatting in Italian about my family. He said, “You have to come back to Italy. You’re like Freddie Mercury — go to Abruzzo, the top of the world, and write and be inspired.”

Sounds great, Luca. I’ll go back to San Donato tomorrow. :)

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Meeting Captain America…

You know what they say about Italian men… don’t make eye contact. I made that mistake while Rachel and I were having a nightcap at one of my favorite bars, and two older men immediately took it as an invitation to join us. We’re doing things for the plot, so we entertained it.

Turns out, they’re voice actors — and the one who made eye contact? He voices Captain America in the Italian dubbed films. He told me he’s the Italian voice of Chris Evans. His other claim to fame? Spider-Man. Tobey Maguire Spider-Man. Naturally, we taught him how to play Kill, F*ck, Marry: Tobey Maguire, Andrew Garfield, Tom Holland. (And if your answer isn’t Kill Tobey, Marry Andrew, F*ck Tom… we can’t be friends.)

And no, they weren’t lying — we saw the proof on Instagram. Rachel, on the other hand, was a master method actor. Channeling How to Lose a Guy in 10 Days, she told them she was a therapist. When they started asking questions, she just giggled and said, “What do you mean?”

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For paid subscribers 🔒

• San Donato !!!

  • Hometown Date

  • Citizenship & Family Secrets

  • The Bakery & the Blessing

  • Old Friends

  • The Real Bakery

• Dream Money, Old Identities & the Art of Becoming

If you want the full stories head over to the full diary below! ✨