The Break Room Crew (Claire, Roberta, and James) at Robinson's Software and Design have placed a bet during the Holiday season. Mostly, because Claire has decided it is her mission to help her boss, Sarah Alexander, find love. Well, the reality is she wants to set her boss up with her brother, Jeremy Buchanan, in hopes to make her boss a little more perkier during the holiday season. James doesn't think Sarah is capable of love. Roberta thinks Claire may be on to something. Will Sarah go on a date and kiss Jeremy by Thanksgiving? Will Jeremy propose to Sarah by Christmas Day? Claire is betting and determined to win.