Directed by: Alejandro Agresti
Starring: Christopher Plummer, Keanu Reeves, Sandra Bullock, Ebon Moss-Bachrach
Revealing mistake: When Kate kisses Morgan in front of 1620 N. Racine, the camera moves up through the branches of a tree. You can see one of the lower branches shake when it is bumped by the crane. (01:17:20)
Revealing mistake: Kate's birthday is July 10th. When she is (with long hair) outside on the patio with Alex, you can see their breath as they talk, and there is not a living thing in the back yard, it's all dormant (as in late fall/winter).
Continuity mistake: When Bullock is warning Reeves of the coming winter blizzard, she is looking through pictures that depicted her and her friends enjoying the snow. She then turns to the dog and asks "Remember that day? You were not happy". However it's revealed that both characters have the same dog, given to Bullock's boyfriend by Reeves, so when the snow happened in Reeves' time - 2004 - the dog was with him.
Kate: One man I can never meet. Him, I would like to give my whole heart to.
Trivia: 1620 Racine is the same block as in the movie The Untouchables. The address where Sean Connery is killed is 1634 N Racine.
Question: Why did Alex have to wait until Valentine's Day 2008 to meet Kate? Even assuming for the sake of argument that the "time-traveling" letters stopped after Alex avoided the bus accident on "his" Valentine's Day 2006, Alex certainly knew how to find Kate at that time - and vice versa. The two-year gap where Kate had not known about Alex had closed by that time, and each knew about the other.
Answer: Kate asked him to wait, and come in 2008, so that's what he did. Likely they could have found each other before then, but it might not have even occurred to either of them.
They started communicating after he died in 2006 (her time) on his way to see her, but 2004 his time, neither of them knew he had died by this time so there was no way they could have met, my question is how did he know to go and meet her the first time if they hadn't started communicating yet?
They had been communicating for 2 years at that point - his time. Hence why he was going to meet her and got killed in the process.
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Answer: The movie is not about them trying to find ways to meet. They are not trying that hard to meet and the time distance is a metaphor. I think the movie misses the tension that she is trepidatious about meeting and he is trying to respect that. He gets killed the first time for trying to force it! This shows when the stack of letters is piling away. She is worried he is a coward who will not be able to handle real romance. This is shown in his retreat to build mass produced houses and has something to do with his mom/dad. She's the doctor, he's the architect: she saves people for a living and is hung up about her own father's death. It's only when it's life or death that she gets over it and he also figures himself out and stops trying to fix everything.