Garrett and Justin met because Garrett is Tessa's brother. He would have gotten this slot by default due to the familial relationship, but Justin can honestly say he may have earned this spot even if he weren't a Barclay. Justin's interactions with Garrett were initially limited to holidays, family gatherings, etc., but that changed in 2017 when Garrett, in a post-collegiate soul-searching effort, ended up living in Justin and Tessa's living room for three months. With Tessa mostly occupied by med school, Garrett and Justin were forced to develop a friendship lest they wanted to coexist with each other in silence for 90 days. It turned out that Justin actually really liked Garrett and saw a lot of himself in him. Garrett has since moved out of the living room, but only made it as far as the apartment building next door. Despite the distance, Justin and Garrett's friendship maintains itself through early morning trips to the UVM gym, happy hours at the OP, and home-cooked dinners. Given the proximity, Tessa and Justin actually communicate with Garrett via walkie-talkie, even using code names during transmissions. It's kind of cool in a pathetic, nerdy way. Garrett hails from San Diego, graduated from UCLA, and, as mentioned previously, now resides next door to Justin and Tessa in Burlington, VT. He works at a marketing firm in town and likes to sign off his emails with "Best, Garrett"--respectful and professional, but short and sweet to drive home that he's busy and important.