Complex sentence: In 2010, Caitlin performed with Matt Douglas (lead singer and songster for The Proclivities) in Raleigh's annual Love Hangover show, in which male/female duos sing love song covers.
Split into simpler sentences: In 2010, Caitlin paired up with Matt Douglas, the lead singer and songster for The Proclivities. They performed in Raleigh's annual Love Hangover show, which features a male/female duo singing love song covers.