Every day, Boston Globe advice columnist Meredith Goldstein takes on the relationship problems of thousands of dedicated readers. In her column, she has it all figured out, but in her real life she is a lot less certain. Whether it's her own reservations about the traditional path of marriage and family, her difficulty finding someone she truly connects with, or the evolution of her friendships as her friends start to have their own families, Meredith finds herself looking for insight, just like her readers. As she searches for responses to their concerns, she's surprised to discover answers to her own. But it's after her mother is diagnosed with cancer that she truly realizes how special her "Love Letters" community is.

Beth “Bee” Evans’s first vow as a bride is that everyone on her list be invited to bring a guest to her lavish nuptials. When Hannah, Vicki, Rob, Joe and Nancy one by one decline Bee’s generous offer, the frustrated bride dubs them the “Singles,” adrift on her seating chart as well as in life.