Gallery

Here's a timeline of our love through photos!

Oct 2019 - The day after Drew and Jessie met! On their walk home, Drew asked Jessie on their first date.

Nov 2019 - Jessie broke her ankle a week after meeting Drew (climbing accident!). Their first few months together were spent with Jessie on crutches - she joked that she was 'head over boot' for Drew.

Nov 2019 - Less than a month after Drew and Jessie started 'officially' dating. Jessie forced Drew to do a photoshoot at Chautauqua.

Apr 2020 - What was supposed to be a short 2 week COVID quarantine turned into a 2 month stay at the Lawley residence. Fun fact: this was also Jessie's first time meeting the Lawleys!

Aug 2020 - Jessie's first Dealmaker trip! Jessie won over the Lawley's with her interest in fishing. Some say she even tired out Sean...

Dec 2020 - Drew and Jessie's second winter spent together in beautiful Boulder, Colorado.

Aug 2021 - Drew and Jessie made a surprise trip out to Sacramento for Mochi's homecoming! Little did they know how much they would grow to love this dog...

Dec 2021 - Mochi's first Christmas! This was the beginning and end of Drew and Jessie's matching pajamas tradition...

Dec 2021 - Drew and Jessie rang in the new year with both of their families in La Paz!

Feb 2022 - Climbing was a huge part of Drew and Jessie's relationship in college.

May 2022 - Drew and Jessie graduated from CU Boulder! Sko buffs!

Jun 2022 - Drew and Jessie moved into their first apartment together in Texas!

Feb 2023 - Drew and Jessie took a big step and purchased a house together!

Oct 2023 - Celebrating 4 years together! Jessie brought Drew to this photo studio for their monthly surprise date night.

May 2024 - Another Mexico trip spent with great company and amazing views!

Aug 2024 - Drew executed a flawless proposal! (Note: Drew wrote this caption)

Aug 2024 - Moments after Jessie said 'yes'! Little did she know there was another surprise coming...

Aug 2024 - Jessie's reaction when she saw the second surprise Drew put together.

Aug 2024 - ...the surprise. Drew and Jessie are so grateful for their amazing friends that made the engagement weekend unforgettable!

Dec 2024 - Drew and Jessie moved to New York, then celebrated the holidays in Mexico with the Lawleys.

Feb 2025 - Drew and Jessie making it through their first New York winter!

Apr 2025 - Drew and Jessie made a trip out to AZ for wedding prep!

Jun 2025 - Drew and Jessie took engagement photos in Central Park!

Aug 2025 - Drew and Jessie finally joined in on the Euro Summer trend.

Sep 2025 - Jessie and Drew went to Korea for the first time!

Oct 2025 - Drew and Jessie had a great time at their Bachelor/Bachellorette parties in San Diego!