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Once your boyfriend joins, if he is qualified and makes it through MEPS, he will then take a 1-1-1 with his recruiter. 1-1-1 being, 1 minute of push-ups, 1 minute of sit-ups, and a 1 mile run. Yes, he will take a PT test at any time of the year, unless the recruiter does not have a place to conduct the PT test, during the winter. He will most likely take a PT test with his recruiter, once every month, until the day he ships. I am going off of my recruiter's system, but I expect it to be similar for all future soldiers.