Jim moves to NYC into what will become our 750-square-foot home in Chelsea.

Like proper millennials dating during a pandemic, WE MATCHED.

Jim asked Allynn "out" on our first Facetime date when Allynn refused to save his number because this wasn't going to go anywhere.

Allynn said bye to Indiana and the greatest pandemic roomies around!

Our first in-person date on NYE 2020! Allynn landed in New York and went straight to Jim's apartment, much against the advice of all of her friends who rightfully feared a stranger from the internet.

First day-time date on a walk through one of our favorite neighborhood spots, Chelsea Market.

Our first vacation together up to Vermont to see our dear friends Nicole & Ben Green!

Allynn asked Jim to officially start dating and he replied "Oh, I was already dating you."

DC for Easter.

WE GOT ELAINE and Allynn officially became the second most important woman in Jim's life.

Celebrating Allynn's Masters Graduation from Columbia.

Officially roomies! And yes, the cat moved in before Allynn did.

Vacation to the beach in North Carolina.

Celebrating Allynn's new job at Kivvit.

Celebrating Kelly and Joey's wedding in Chicago.

Celebrating Jim's new job at Splunk.

The one and only time we will ever road trip with our cat.

An early McSheppard Christmas 2021 in NYC.

Hawaii for New Years 2022.

Our 1st Anniversary in Clearwater, FL visiting Jim's family.

Celebrating Alex and Will at their wedding in the Rainbow Room in New York!

Celebrating Twyla and Chris's wedding in Dallas, TX.

Jimmy's Oxford MBA (very belated) Graduation!

Portugal for Jim's MBA graduation present.

Celebrating Allie and Sam's wedding in Mystic, CT.

An early McSheppard Christmas visiting the Elloy’s in Belgium and Germany.

Our 2nd Anniversary in Vegas where we won playing the '2' in one hand of roulette.

Celebrating Sarah and Sam's wedding in Davis, CA.

Earlier in our lives, we both lived in San Francisco - we took a vacation back to the West Coast to show each other our favorite parts of Northern California.

Getting the most important proposal approval.

Allynn was too shocked to even say yes.

Jim forgot his wallet on the way to the airport and missed his flight, so Allynn enjoyed a little engagement party as our parents met for the first time... without the groom!

Celebrating our friends Julie and Nitesh at their Chicago wedding.

Celebrating Allynn's promotion to Associate Director at Kivvit.

Jim's new job at Google in Chicago!

Ended 2023 wedding season dancing until 4am with Caroline and Stefan at their wedding in Stuttgart, Germany.

Allynn made Jimmy take engagement pictures!

We packed up our Chelsea home and said goodbye to our New York chapter.

Moved into our new Chicago home!

Our daughter turned 3.

A very merry Chicago McSheppard Christmas 2023!

Jimmy's work conference in London.

Celebrating our dear Catherine's baby shower in Jacksonville, FL.

Celebrated our 3 year anniversary the best way possible: On my bachelorette with the best women in the world 🌴