Sally & Ryan
Our Story
City #1: The 6ix
Jan 2019
Sally: At Ryan's recommendation, we first met at The Communist’s Daughter, a quirky bar in Toronto where the bartender sings along with a band. Honestly, I just remember being extremely hungover. But, I was impressed with Ryan's date suggestion, until I realized he brought all his first dates there to seem cooler than he is. Ryan: Sally was late and clearly hungover, but she charmed me with her weird wit and cute Asian glow. Plus, she seemed genuinely impressed with my bar choice, which I’ll admit I took as a win.
City #2: Beantown
Oct 2020
Sally: Ryan moved to Boston for what was supposed to be a “short stint.” I followed him, got a new law firm gig, and discovered the joys of earning USD and clipping coupons in the CVS app. Ryan: I was supposed to hire a team and head back to Toronto, but Sally showed up, and suddenly my “short stint” became the first city we called home together. Boston was where we learned how to cohabitate during a pandemic—and not kill each other.
City #3: The Windy City
July 2021
Ryan: Chicago was next. I had another team to hire, and we traded in clam chowder for deep-dish pizza. We swam in the lake, explored the city, and realized “Midwest nice” is a real thing. Sally: Ryan fully embraced his Midwestern alter ego—too cheerful and way too into saying “hi” to strangers.
City #4: Meeting Karl The Fog
Oct 2021
Sally: My office in San Francisco called. Ryan had to soon move to Philly, but I made the most of the West Coast—strengthening my glutes on those hills and figuring out how to thrive solo in a city that’s 70% tech bros. Ryan: I’ve never lived on the West Coast, and honestly, I don’t trust any place without proper seasons. But I’ll admit San Francisco is ridiculously pretty until Karl the Fog shows up.
City #5: Philly Cheesesteaks
Nov 2021
Ryan: Work took me to Philly, while Sally split her time between SF and Philly. The city had its charms—cobblestone streets, great food—but honestly, Philly cheesesteaks didn’t live up to the hype. Sally: Philly was cute but felt like a layover in our journey. It did give us a chance to practice juggling long-distance-ish life, which was its own kind of challenge. And for the record, Philly’s food scene is very solid and they do a good Christmas market.
City #6: The Capitol
Feb 2022
Ryan: D.C. was a vibe. We lived in Georgetown, crashed embassy parties, and hit every free museum we could find. I was there to launch another team, but we made time for a little fun. Sally: D.C. brought out our cultured sides—or at least our ability to pretend. I'm just glad we got to experience this city before the ahem.... new administration.
City #7: Back to City #3
April 2022
Sally: Chicago: Round Two. Ryan went back to set up his new US HQ, and I decided to light a lot of money on fire by quitting my job and pursuing an MBA at Kellogg. Ryan: Let’s be honest—Sally’s MBA was a “we” effort. She delegated the spreadsheets and PowerPoints to me, and I pretended to know what I was doing. We made it through thanks to teamwork—and deep dish.
City #8: Lion City
January 2023
Sally: I went to Singapore for an MBA exchange at INSEAD and proceeded to travel like a maniac and consume inordinate amounts of laksa. Ryan joined later, and we embarked on an epic travel adventure through Asia and Europe as I finished my MBA. Ryan: Most notably, I proposed at sunrise on a volcano in Java. Sally said yes, probably because she was worried the volcano might erupt if she didn’t.
City #9: Back To City #1
Aug 2023
Sally: We returned to Toronto, reconnecting with friends and trying to figure out what “settling down” even means. I got my first in-house job, and we got a brief taste of normalcy. Ryan: But normalcy didn’t last long. Turns out, we’re not great at sitting still.
City #10: The Big Apple
April 2024
Sally: After all our adventures, New York felt like the logical next step—or at least the place where we could stay busy enough to avoid thinking about our next move. I joined a legal AI startup and Ryan started his own company. We’ve been eating our way through the city and probably working too much. It’s busy, chaotic, and perfect for us. We can't wait to welcome you there! Ryan: NYC is everything people say it is: loud, fast, and full of way too many pizza options. But between the restaurants, Broadway shows, and the occasional park escape, it’s starting to feel like home. Just don’t expect us to sit still for too long—we’ve got a track record to maintain.