Director Nancy Meyers, Elaine Hendrix (Meredith), Lisa Ann Walter (Chessy), Simon Kunz (Martin) and writer and producer Charles Shyer joined Lohan (Hallie and Annie) and Quaid (Nick) during the reunion which was uploaded to Couric's Instagram page.
The special is raising money for World Central Kitchen which provides meals to those in need.
"I had such a blast doing this movie. The first thing I remember was meeting Lindsay at, I think it was some kind of a screen test. I remember thinking, 'Oh my god that's one of the most talented people I've ever met period. Forget that she's 11 years old," Quaid said.
"My parents were kind of separating at the time, when this was all going on and it made it a lot easier for me to play these characters that were figuring it out. I just felt so lucky and really blessed by Nancy and Charles," Lohan said.
"Without this movie, without this I wouldn't have gotten that acting bug," she continued. "How do you not want to only act for the rest of your life after doing a film like this with such great actors? The Parent Trap. It's beautiful. It's timeless and it's special."