Peter Klaven's world revolves around his real estate work and Zooey, his soon-to-be fiancée. After he pops the question, she calls her best friends and they go into wedding planning mode. Peter has no male friends and that poses problems: will he turn out to be a clingy guy, and who will be his best man? Zooey, her friends, and Peter's brother Robbie offer help that results in awkward moments. Then, at an open house Peter's hosting, he meets Sydney, an amiable, low-key guy. They trade business cards, and Peter calls him to meet for drinks. A friendship develops that's great at first but then threatens Peter's engagement and career. Can guys be friends and couples be in love?

Reuben Feffer thinks he's found the love of his life but on his honeymoon he discovers her cheating on him with a scuba instructor. Reuben travels back home to get his life on track. On a night out with best pal, Sandy Lyle, Reuben discovers an old school friend, Polly Prince. Reuben feels a connection straight away, and tries constantly to get her to like him. But it's not going to be easy for Reuben, especially when he spends his days calculating risks, and when someone unexpected turns up.