First of all, I will say that I doubt the writer even knows the answer, as it probably is not supposed to have one. A true mystery.
But I don't think it's Sherry who wrote it, although it is (of course) possible.
Argument against her writing it:
Wrong envelope size, wrong paper size. If she had a stack of envelopes and pink paper at home, it would be the same size. It's possible that the envelope is bought individually, but how many different sizes of pink paper do you keep at home? So the wrong paper size leads me to believe it's not her who wrote it.
Also, just because it's pink paper with red ink, doesn't mean it's her who wrote it. She saw it in the foyer upon leaving Murray and said it was probably from one of his lovers. A pink letter with red ink stands out and it is far more likely to remember this than envelope size.
Winston says the handwriting "might match", but since he also notes he have to compare it with the other letter, I'd say that is not conclusive.
Argument for her writing it:
She could've specifically picked up the mail to point towards her own pink letter, to make sure Murray was aware of it, and push him on a quest with the goal that he'll later be more inclined towards settling down.
I'm just not convinced by it.
There's too many 'coincidences' in the movie for it to be Sherry who wrote it.
-The kid on a road trip in the end. It was a small area, it doesn't seem like a place people just road trip through. And it wasn't a REAL random road trip. He got there through the airport (so he didn't just hitchhike from somewhere) and then he makes it to Murrays small neighborhood, not exactly being a place people randomly road trip through. And he has a pink bow on his backpack that his mother put there for "good luck". Again, much coincidence the kid showing up at that time and with a visible pink bow on his backpack. And his father is a touchy subject.
-At the dinner with Dora and Ron, Murray asks whether they have children. Ron says he always wanted children with Dora, specifically making a deal of it being "of their own", and Dora replies she doesn't think she would have been a good mother with enough patience to care for Ron's children. Not just children, but RON'S children. This could be interpreted as they have no children at all, but to me it sounds like there is a kid of Dora's from before she met Ron. Also, Dora's business card was pink, there was a lot of pink in the house, it wouldn't be too far fetched to assume there would be pink paper in the home and red ink to match the decor, especially since they deal in designer homes, so they'd have stationary to match for the aesthetic looks.
-Penny had a pink typewriter outside in the grass. She was very upset about Murray asking if she had any kids, meaning it's a touchy subject; dead or run away. She could have been upset about the kid wanting to find Murray, but felt she had to write to him, after which she was so upset she threw the typewriter outside. A bit of a stretch, I will admit as well though, since the kid's pink bow on the backpack for "good luck" seems to indicate he left his mom on good terms.
-I was first inclined to write off Michelle (dead woman), because she is dead. But the pink bow made me think just now... It's possible she was on her deathbed, and confronted with losing his mom, the kid wanted to find his father. Michelle then gave him the pink bow for luck, and then wrote to Murray. She then dies and the kid leaves to find Murray. The only thing not fitting this, is that in the time between the letter and her death (and burial) I would assume there would still be flowers by her tombstone after the burial. Or it would appear newly dug, which it wasn't. Also, it appears weird that the kid arrives at the airport around the same time as Murray, even though he has spent like 5 days traveling. But that can be said about all the women.
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exophase
9 years ago
I think there are a lot more arguments than that for Sherry being the author of the letter.
1) The letter just so happened to have arrived just as she was leaving him, big coincidence if those events aren't connected.
2) Sherry had no good reason to suspect the letter of coming from some "other girlfriend" except that it was pink, there wasn't even a sender on it. And if she's going to accuse him over the flimsiest thing like this it's a wonder how they still stayed together. It sounds like she already knew that the letter was supposed to be from a girlfriend, or ex-girlfriend anyway.
3) If she really just wanted to leave him she shouldn't have cared about the letter to begin with.
4) She is clearly invested in having children right as Don allegedly learns he has a child. She has a clear motive for faking the letter, to test Don to see if he actually has interest in being a father, maybe because she knows she doesn't have a lot of time left.
5) And she coincidentally wants to get back together with him as soon as he returns. Maybe because she learned about the trip and realized that he was in fact interested in his alleged child.
6) On the other hand, I can't think of a reasonable motivation for an actual ex to have sent that letter. Why decide at this point to inform the father that he has a son but not say anything about who the son is or who she is for that matter, nor give any possibility for meeting him? That just seems cruel, yet the tone of the letter doesn't make it sound like it's just tormenting him.
7) To me it seems obvious that none of the ex-girlfriends he met were the mother. The note seemed to describe that the son was raised by the mother, something I don't think fit into any of the lives we saw or heard described. So then the question is, why wouldn't he have found the mother after narrowing it down to all possibilities?
8) The movie foreshadows this when Winston says (and Don agrees) that Sherry still had another card to play.
As for the coincidences that suggest otherwise...
1) If the backpacker at the end was there looking for his father why did he freak out like he did? Doesn't seem to add up at all, and it doesn't seem like that big of a coincidence for him to be there anyway.
2) Dora would have had no patience to care for Don's children either since it's pretty clear that Ron didn't raise this son with her. We can surmise that Ron's been with Dora a while or else the question of having children would have probably been moot in the first place (since the actress, and probably the character is now over 50)
3) Penny's behaviour doesn't seem remotely consistent with the letter writer's. The writer seemed to be okay with the breakup, while she hated his guts.
4) Winston says Michelle died 5 years ago. She couldn't have simultaneously been someone Don dated about 20 years ago (that was how he and Winston narrowed down the list - and I think we can fairly assume that Don wasn't with any of his girlfriends for several years back then), had a 19 year old son at the time of writing the letter, and been dead for 5 years. That's already figuring that somehow the letter was somehow mailed years after she died.
The wrong paper size hardly means anything. Maybe she happened to have multiple sets of stationary. There are all sorts of trivial explanations for how that could happen.
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