Preschool teacher Sarah Nolan (Diane Lane), divorced for eight months, is still grieving the end of her marriage. Although she didn't see it as being perfect, she probably would have stuck it out as what she saw as the "for better or worse" obligation of the wedding vows, that is if her ex-husband, Kevin, didn't end it for what ended up being leaving her for a younger woman. She is urged by her over-supportive family, comprised of her many siblings, their partners, and her widowed father, to get back into the dating scene, something she has been reluctant to do in not feeling ready. As such, her most proactive sister in the matter, Carol (Elizabeth Perkins), sets her up on an Internet dating site. Within her less than prepared state, Sarah does go along with meeting men by the means offered to her. Beyond especially her female siblings, Sarah is given unique perspectives on the whole issue of dating and commitment by her father, Bill (Christopher Plummer), who is exploring dating after losing who was the love of his life in Sarah's mother, thrice divorced Dolly (Stockard Channing), one of Bill's conquests, who he meets on-line, and Sarah's gay teaching colleague, Leo (Brad William Henke), who she sees as being in the most committed loving relationship with his partner Eric (Victor Webster) of anyone she knows. Of the men she meets, Sarah makes what she believes is a connection with two, albeit awkward in both cases. One is Bob Connor (Dermot Mulroney), the divorced father of one of her students, her hesitance in dating him only because of crossing the professional/personal line. The other is custom wooden boat builder Jake Anderson (John Cusack), who too was pushed into trying on-line dating by his best friend/divorce lawyer Charlie (Ben Shenkman), who wants Jake solely to get some action despite Jake wanting his love life to be more like Lara and Yuri in Doctor Zhivago (1965). Much of what happens between Sarah and the two men is based on what stage they are in post-divorce dating life, but is also dependent on how much Sarah is willing to take a chance on each, which may also include her and the respective man just not meshing at a given point in time, and her making a wrong decision in the process based on what she sees as the prospects.