LESTER is a cartoonist by day and a single guy looking for “love” by night (and day). He was recently dumped by his girlfriend of three years. Suddently single, he’s back in the wild world of dating. Lester is a typical guy. He’s not sensitive and he’s not particularly funny. But, of course, he thinks he’s both sensitive and funny. With the help of his guy-friends, Lester tries to get back on his feet, face single women, and perhaps collect their phone numbers/emails. It’s a slow process and he struggles mightily. Hell, sometimes it’s unbearable to watch, but his friends cheer him on.
SYDNEY is Lester’s only female friend. She tells him like it is. She doesn’t sugarcoat anything. Sydney is Lester’s personal reality-checker. She also has her own dating issues. She asks Lester many questions about men in order to better understand them. However, she probably picked the wong subject to interrogate.
GUS is Lester’s childhood friend. He’s a lawyer and is in a long-term relationship with Lynda. It’s pretty obvious to his friends that Lynda is the one who’s in control of their relationship. Gus, on the other hand, doesn’t see it that way. As a result, he believes that he’s an expert in relationships and tries to help Lester find his “true love.”
VINCENT is also Lester’s childhood friend. He’s the complete opposite of Gus. He has major commitment issues and dates different women every week. He has different view-points about relationships compared to Gus and he’s not shy about sharing it with Lester.