Here you meet Holly's several friends, as they engage in some drinking and weeping, all sad and especially worried about her. Here's where you also meet Daniel (Connick), awkwardly and seriously crushing on Holly in a wholly inappropriate and strangely inoffensive way.
Holly puts on a bit of a show herself, as the I-can-cope grieving widow, while coupled friends Sharon (Gina Gershon) and John (James Marsters, reminding you how much you miss Spike) offer standard support and unmarried Denise (Lisa Kudrow) hits on random men at the bar ("Are you single? If only, you begin to think, this romance gets under way soon, and Connick can bring his peculiar charms to the proceedings. Daniel is more or less disappeared from the film at this point, leaving the bulk of the emotional work to Holly, who is definitively not up to it.
" he wonders about women, feeling forever lost when it comes to pleasing her or other unseen objects of flirtation.
Treating her to an "Irish" memorial and corned beef sandwiches, Daniel gives up.
It's not a little depressing that Holly, seemingly capable if slightly manic before Gerry's death, is so seemingly unable to function without his from-beyond guidance.
While the letters-leading-to-flashbacks device occasions something like an explanation for her devastation (really, he was all the fun in her over-planned, under-improvised life), it also limits her characterization to memories of moments with him.
At the same time, Holly gets her first dose of the movie's gimmick, the year's worth of posthumous letters from Gerry, arranged to arrive every day.
He just knew that she wouldn't have a "plan" for her widowhood (and who would?
Which brings us back to Daniel, who finally reenters the picture just when Holly's deciding on a new career and looking more forward than back.
He offers more clumsy hopes for romance and a few choice moments: "What do you people want?
For all his plain-speaking, down-homey affect, Harry Connick, Jr. While it's easy to appreciate his dedication to New Orleans' recovery or his uncanny appropriation of Sinatra's swing, his movie career is curious. I Love You, a miserable holiday romance ostensibly starring Hilary Swank as worrywart Holly and Gerard Butler as her gorgeous husband Gerry.