I turn 66 January 2019. I want to file for my S.S. My question is, do I file 3 months before Jan 2019 in order to receive my first check in Jan?? (or how soon to apply... I still want my checks to start my birth month in 2019)
If your birthday isn't on the 1st of January and you want to receive unreduced benefits, then your first payment won't arrive until February 2019. Social Security benefits are paid in the month after the month for which the benefits are payable.
You can file up to 4 months in advance so you could file as early as September 2018, but filing in November or December should give Social Security plenty of time to pay you timely. Before filing, though, you may want to strongly consider using our maximization software to explore all of your filing options and decide on your best strategy.