Jillian Boshart rewatches P.S. I Love You and ponders the film’s lasting questions: Are Gerard Butler’s letters sweet or fucked up? Is Jeffrey Dean Morgan’s penis a cure for grief?


[Content Warning: This review contains a brief discussion of suicide and a lengthy discussion of grief.]

Merry Christmas from Cancer, everyone! I’m here to talk to you about the romantic not-really-a-comedy P.S. I Love You. Or as I like to call it, A Little Film About Grief.

I think a very brief synopsis will serve this purpose. Holly (Hilary Swank) and Gerry (Gerard Butler) are a couple who met as very young adults. Ten years later, they are waiting for their lives to begin. Gerry is diagnosed with cancer and dies, leaving Holly a widow at 29. We discover that Gerry has organized a series of letters to be sent to Holly over the year after his death. The bulk of the movie (literally, Gerry is in the opening scene of the film, and the next scene is his funeral) is her receiving these letters, doing as they instruct, and learning how to cope with her loss.

I’m stumbling around trying to write how I feel about this movie, so I’m just going to rip the band aid off:

My mom died by suicide in the summer of 2015. This was a shock to all of us to say the least, though I suppose death in this manner is almost always a shock. My family has not been public about this, though I have told friends when I have needed to. She did not leave a note.

I really wish she had left a note.

For weeks I lived in the space of magical thinking that grief puts you in. I imagined I’d find a letter in the mail from her explaining why she ended her life, and by extension mine as I knew it. Mine in which I was still somebody’s child, not quite a real adult, because I could still fall and my mommy would catch me. This letter, of course, never came. But I craved it. And writing this now, I still do.

So for me, ten years later, watching this movie is like pushing a bruise. Like, does this still hurt? Oh yes, yes it does. But it is still helpful to watch such an honest portrayal of grief. It makes me feel less alone. And, in a sense, it feels good to put myself in Holly’s shoes and imagine that her experience of coming out of grief was my own. Fantasy is powerful, I guess.

Hilary Swank’s portrayal and the script’s treatment of grief is so lovely and honest. She still makes two cups of coffee in the morning. Their last fight spins on repeat in her head. She wallows in mess. She wakes up having forgotten he is dead. She gets angry when people are moving on. Her friends even come and clean her apartment (which happened for me as well, and to you all that did that: I am still so grateful). It is all so real.


The movie has flaws, to be sure. Harry Connick, Jr.’s entire storyline could be removed entirely, and it would serve the story better. But chiefly, one wonders: should Gerry have done this to Holly, or should he have let her move on in her own way? Are his letters selfish, or are they kind?

I suppose they are both. The letters aren’t just sweet gifts to Holly, but also Gerry’s way of coming to terms with his death. His way of continuing to live. Even still, some of the letters are incredibly practical, like when he instructs her to keep his leather jacket, but pack up and give away the rest of his clothes. Those sorts of mundane decisions are incredibly hard when in the grip of grief.

All in all, this is a sweet movie. And if you too have felt deep, life-altering grief in your life, you may find it to be a mirror. And you may, like me, find it to be helpful in your healing.

Random Thoughts:

A million people are in this movie. Including indie music sensation Nellie McKay, one-time vampire James Marsters, and terrible Broadway actress Sherie Rene Scott. Oh, and Kathy Bates!

Lisa Kudrow is also in this movie. At one point her character is criticized for treating men like meat and she says, “And let me be clear; after centuries of men looking at my tits instead of my eyes, and pinching my ass instead of shaking my hand, I now have the divine right to stare at a man’s backside with vulgar, cheap appreciation if I want to.” I pumped my fist. It was great.

And as I said, Harry Connick, Jr. is also in this and his entire storyline could be removed. But here’s the thing: if they did remove each of his scenes and strung them all together, it would be a very good short film of a man with Asperger Syndrome trying to date. Like, legitimately, it would be a good portrayal of someone trying to date while living as a person with autism.

Oh, lastly…Jeffrey Dean Morgan is in this and oh boy, you see his butt, and it is glorious. Holly has a one-night stand with him in an attempt to move on. It is great to see media in which JDM’s character gets to be alive the whole time. His presence made my watching party of three pause the movie to have a very long conversation regarding whose dick we think is bigger: Jeffrey’s or Gerard’s. We settled on Jeffrey’s, since he gives Holly the Good Dick of Emotional Healing. Actual quotes from that discussion:

  • “Jeffrey Dean Morgan’s is the penis for all occasions!”
  • “So, I feel like, we don’t need Therapists. We need Jeffrey Dean Morgan’s penis.”
  • “I really want a supercut of Jeffrey Dean Morgan lying in bed with all of the sad women he has died for, or like, placated with his penis.”