Popsugar Entertainment Valentine's Day TV Characters From Different TV Shows Who Should Date TV Matchmaker: Characters From Different TV Shows Who Should Date February 15, 2014 by Shannon Vestal Robson View On One Page Photo 3 of 9 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 3 Olivia and Will Her: Olivia from Scandal Him: Will from The Good Wife Why they'd work: These two are both so driven in their careers and would understand each others' schedules and independent streaks. In short, he could "handle" her. Previous Next Start Slideshow Valentine's DayTV