Backdate/Antedate an entry
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Is it possible to create an entry for something that happened on a date prior to the date of creating the entry?
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Absolutely you can! If you add a photo from the past, Day One can prompt you to update the entry date/time if the photo has that data.
You can edit the date/time/location of any entry. https://dayoneapp.com/guides/tips-and-tutorials/change-the-date-time-of-an-entry/
Also, you can use the Calendar to add an entry in the past. https://dayoneapp.com/guides/tips-and-tutorials/calendar-view-in-day-one/