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| Hilary Swank | Holly Kennedy |
| Gerard Butler | Gerry |
| Lisa Kudrow | Denise |
| Gina Gershon | Sharon |
| James Marsters | John |
| Kathy Bates | Patricia |
| Harry Connick Jr. | Daniel |
| Jeffrey Dean Morgan | William |
| Nellie McKay | Ciara |
| Dean Winters | Tom |
| Anne Kent | Rose Kennedy |
| Brian McGrath | Martin Kennedy |
| Sherie Rene Scott | Barbara |
| Susan Blackwell | Vicky |
| Michael Countryman | Ted |
When Gerry, the husband of Holly Kennedy, dies from an illness, she loses the love of her life. Knowing how hard Holly will take his death, Gerry plans ahead. Beginning on her 30th birthday, she receives the first in a series of letters written by him, designed to ease her grief and encourage her to move forward to a new life.
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