Was a step recorded that deletes the existing date? If not, try copying the step that sets a new date. Paste it and drag it above itself. Double click the new step and change the Text field to be blank. You can also try to enable "SimulateRealTyping" on both steps.
To ensure the date field is blank before proceeding, insert a Verify or Wait step that checks if the content is blank before the date selection step. That process is outlined here
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