If your Paid Family Leave was not reported on your W-2 then no, you would not check the box for paid family leave after entering that W-2. When you enter your W-2, the questions after the W-2 are only related to income on the W-2 you had just entered.
If you received a 1099-G for your paid family leave, this is reported separately under Unemployment in the Income section.
Where do I report a 1099-G for unemployment or paid family leave
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