Pretty and demure, Maureen made the perfect society wife for the politically-ambitious Trip Vanderbilt. The couple got married in Season 2 -- an event that engineered a short-lived reconciliation between Nate and his grandfather, William Vanderbilt. Trip and Maureen later returned to the show as Trip set his sights on Congress...and Serena set her sights on him. We're not sure how Maureen will react to that news but here's hoping she has something devious up her sleeve. She was the mastermind behind the Hudson River scandal after all!