How many days late should you test at?

According to this app im a week late. But I'm on the pill and I'm 3 days into the placebo pill. I missed about 5 pills(lost the pack) but I caught up. My bf doesn't pull out. My body is acting really strange bloated, random naseau, boobs are really big, last night I had a random sharp pain in my boobs, random aching in my hips, flutters in my stomach,  No signs of period usually i cramp a couple days before. But nothing. Took 2 tests last week when this app said I was late but all negative. Should I test again?