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Level 1

Hello! My fiancee and I are getting married in October of this year. I am starting a new job next week - should I file as married filing jointly now?

I start a new job in May of 2019. I get married in October of 2019. What should my tax status be from May to October? Single? Married filing single?Married filing jointly? Is there any negative implications to choosing a married status from now until October, or is it in my best interest to file as single until I am legally married?

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Level 11

Hello! My fiancee and I are getting married in October of this year. I am starting a new job next week - should I file as married filing jointly now?

Does your fiancée work too?  You might want to leave the withholding at work to be Single or you might not have enough taken out when you add both incomes together.  Even though filing Joint has the best tax rates your total income will be more.  
Level 11

Hello! My fiancee and I are getting married in October of this year. I am starting a new job next week - should I file as married filing jointly now?

You cannot file a joint return if you are not legally married. If you are getting married in October of 2019 then next year when you prepare your 2019 return you can file married filing jointly. You can change your W-4 at work whenever you want to. That is just for your employer to tell them how much tax to withhold.