GARY (Sasha Andreev)  Gary is an average fellow - at least, he thinks so.  He has aspirations of being a writer, but his real ambition is finding a date.  Unfortunately, Gary is not quite the ladies' man he'd like to be.  Confident in his personality but intimidated by women, he is convinced that his three-year streak of rejection shows no signs of improving any time soon.  Resilient yet resigned, Gary will push forward and seek that elusive date, knowing full well that his chances of success are slim to none.  Lindsay is the object of his affection - whether she likes it or not.

SAM (Emily Fradenburgh)  Intelligent and attractive, Sam could just as easily take the top prize at an academic contest as she could in a beauty pageant.  Passionate and driven, she is starting to wonder whether or not her long-term relationship with Keith has finally run its course.  She is beginning to lose patience with Keith's ignorant and immature attitude towards what is supposed to be an adult relationship, but she is reluctant to throw him away and surrender to the possibility of being alone for the rest of her life - or worse yet - getting caught in a whirlwind of blind dates and annoying dating games.  Her relationship with Keith is far from perfect, but it is familiar, and she hopes to determine whether or not familiarity is enough.

ERIC (Eric Lee)  Eric is a child in an adult's body, but in spite of his juvenile tendencies, he has accomplished the status of Domesticated Husband.  He is happily married and content with his place in the world.  He owns his own home, mows his own lawn - he even has a dog.  But his best friend Gary is in dire need of help, and Eric is more than willing to serve as his wingman - accompanying him on his quest without complaint or hesitation.  Encouraging yet brutally honest, Eric will ensure that Gary stays on target.

TINA (Dawn Brodey)  The female equivalent of James Bond, Tina uses her palpable assets to seduce unwary men without remorse or conscience.  She has never been interested in maintaining a serious relationship with any man; playing the field is just too much fun.  At times a bit too self-involved, Tina is not always able to fully understand what's best for Sam, but she tries nonetheless.  She may not always provide solid guidance for Sam, but she is dedicated to being there for her, and she is more than happy to assist her with finding a new man if that's the route Sam wishes to take.

KEITH (Justen Overlander)  Attractive, athletic and pleasant, Keith would appear to be the perfect mate.  Unfortunately, he's a bit on the slow side when it comes to relationships.  He has a steady job and enjoys doing Guy Stuff with his friends, but when it comes to accountability and maturity, the guy has no clue.  Unaware that he has become complacent in his relationship with Sam, he becomes defensive when confronted - or oblivious to the fact that he's been confronted at all.  He cares for Sam and values his relationship with her, but his inability to see beyond the status quo is what jeopardizes his relationship.

ROACH (Andrew Kraft)  Roach is a firecracker, the life of the party.  Full of colorful language and amusing anecdotes, there is rarely a dull moment when Roach is in the room.  He has little ambition in life other than partying and "scoring chicks", and he is not the least bit concerned about how others view him.  His lack of inhibitions and reckless behavior leave little to the imagination - there's no guessing with Roach.  What you see is what you get - and surprisingly, he's usually harmless.  Roach is a little too scatter-brained to be of much assistance to Gary, but even so, he does what he can to help.

LINDSAY (Keri Bunkers)   Gary thinks of her as an angel, the ultimate sweetheart.  From what he can tell, she's as genuine and kind as she is beautiful.  Gary doesn't believe in love at first site, but Lindsay is a strong argument against his case.  Always friendly and never without a smile, Lindsay is the only woman to show Gary any interest whatsoever.

KAREN (Jane Hammill)  Sam's mother.  Karen's relationship with Sam is a strong one.  She's traditional and wise enough to impart practical and authoritative advice upon her daughter, but still young enough at heart to truly understand her daughter's situation.  Karen is of the "it'll just happen" philosophy - she believes that all things happen for a reason and that everything will work out in the end.  She has always been wary of Keith and feels that Sam deserves better, yet she trusts Sam to make her own decisions without the need to be lectured.