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Edit: After I wrote my response, it seems like you've asked this exact same issue before and got answers so I'm confused why you're still confused. As regards to actually contacting your professors, phrase it just like you did the other two times! Don't overthink this.

The general wisdom here is yes, you should get them updated. My unprofessional opinion: IF you have other letters that are dated 2018, then I think a couple one-year-old letters will be fine. Especially since you are out of school. If you think asking a third time would make them a bit annoyed (you know your professors best), then it might be better leaving alone.

Each adcom is different, and may have different views on an "older" letter. I'm currently applying with one "old" letter out of five, and I have decided not to worry about what I cannot change.
 
It's more of what they might update my letter with. The ones from before were glowing (they sent it to me). They talk about my dedication, studiousness, and how it's a no-brainer I'd excel in med school. I worry that the tone will change now that they know I'm applying two years out from undergrad to something like "although we had expected her to get in traditionally, she will do great with better time management and test taking skills..." 🙄

Anyway, if asked to re-update the date, do LOR writers typically change the content as well?

Have you continued to see them or otherwise commuicate with them regularly? If by your recent interactions, they haave new things to add to the letter, then asking for a new letter is worthwhile. If you've ghosted them for a year and come out of the shadows to ask for a refreshed letter, you are better off going with the stale letter.
 
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