If I have two W-2’s from two different jobs do I need to file twice ?

Nope...you prepare one tax return with ALL your income on it.

When you get done entering one W-2, and any followup questions that follow it.... you will then be able to add another W-2 from the other employer.  Make sure you enter them both, separately....but into the same tax return.     

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You are only supposed to file your taxes once..with everything in it.     There is away to correct a mis-filed tax return at later date (by "amending" the original) , but that requires mail-filing of the amended data and can take several months for the IRS to process....and...and you have to wait for the original to be processed before you can "Amend".