Before he died, Gerry wrote, he penned a series of letters with challenges and advice to help her move on that Holly will receive over time. At first, the game seems torturous. Gerry makes Holly sing karaoke, which on its own would signal a trial to get out, embarrass herself publicly, and have a little laugh, but there's a backstory to the whole karaoke thing. It's a memory between the two of them. Similarly, he demands she get rid of his stuff (a little spring cleaning helps) but keep his leather jacket, which brings up yet another memory between the two.

When he books her and her friends a trip to his homeland of Ireland (Butler is Scottish, by the by, but who's keeping track?), where she meets an Irish singer/guitarist (and of course gets assaulted with other happy memories with her husband), we can't help but wonder why her friends would insist that going after the Irish singer/guitarist would make her forget her Irish singer/guitarist dead husband. That whole affair gets a little weird when Holly finds out whom the second Irish singer/guitarist is, but that scene gets over its initial creepiness and turns into a sweet one. Even if it is, once again, about her dead husband.

The letter gimmick is simply a way to show the audience a relationship that doesn't really need to be seen in the first place. Hilary Swank and Gerard Butler are inherently likeable in these scenes, which is a great help, but the whole slow, reverse reveal of their relationship feels like a copout. The scenes outside of their relationship are what help hold the thing together. Denise and Sharon's love lives are moving ahead as Holly believes hers has ended. They're the quirky friends, but they don't hold a candle to Daniel. Daniel's response when Holly tells him Gerry died of a brain tumor: "Nice." He says he has no inner censor and blurts out things when they come into his head.

Daniel is the first of the two men that vie for Holly's conventionally obligated need for another man to show she has moved on, and Harry Connick Jr. is quite funny in a role that could be overdone. Holly's mother tries to convince her daughter that the letter game doesn't help (although her repeated insistence seems odd considering what we learn her part in the plan is at the end), and Kathy Bates is also good her, trying to convince Holly that being alone isn't necessarily a bad thing.

The movie is warm, and while the flashbacks are meant to get us weepy, it's not overtly manipulative (i.e., there's no deathbed scene). It is too gushy for its own good and never has the nerve to be about a woman actually dealing with loss. P.S. I Love You is harmless and has its occasional oddball charms, but it is also ultimately conventional (even if the relationship between Holly and Daniel ends unconventionally) and pandering to go along with them.