Screenwriter Susannah Grant makes her directorial debut in this tale of love, loss, and finding new love. Gray Wheeler's (Jennifer Garner) wedding day is not going as planned. Instead of walking down the aisle in her wedding gown, she is at the funeral of her fiancé, Grady, following his accidental death on a trip meant to be his bachelor party. To make ends meet, Gray puts her things in storage and moves in with Grady's roommates, levelheaded and attentive Dennis (Sam Jaeger) and quirky yet lovable Sam (Kevin Smith). With childhood friend Fritz (Timothy Olyphant) in from L.A. and crashing on the couch, it's a full house. Inhabiting Grady's old room, Gray soon learns that her fiancé had been keeping some big secrets from her and may not have been the man she thought he was. Perhaps more importantly, she discovers some surprising things about herself, and her ability to heal and love again.

Each of the characters in this film has to find a way to survive the devastating loss of a man who held them all together. Garner effectively conveys Gray's heartbreak and confusion without going over the top. As Fritz, Olyphant pulls off the role of the mystery man who is always charming but often misunderstood. Jaeger is earnest and heartfelt as Grady's roommate and business partner. But Smith is the scene-stealer here, with deadpan delivery and great timing as a Celestial Seasonings employee spouting philosophical quotes from the herbal tea company's packaging. Juliette Lewis appears as a sexy, slightly flaky, Californian massage therapist who is also a skeleton in Grady's closet.