When should I re-test?

Ann
Hi everyone!! I'm 23 years old and just started TTC for the first time with my bf of 1 year.  Glow has been really accurate when it comes to predicting my period but this month I'm about 2 weeks later than the the app predicted.  My last period ended December 9th.  I tested with a clear blue digital test first thing in the morning yesterday and it was negative.  I've been sore, nauseous at random times, and super tired.  Could these symptoms be PMS or could I be pregnant?  When should I re-test?  I just don't want to get my hopes up then be let down by taking tests over and over :(