//Check for user name, this all executes perfectly fine. ofstream oFile; ifstream iFile; iFile.open("/APPData.dat"); if (iFile.is_open()) { while (!iFile.eof()) { getline(iFile,holdUsername); } //When the WHILE ENDS it jumps straight to "enter selection" down there. }else{ oFile.open("/APPData.dat"); oFile.close(); iFile.open("/APPData.dat"); if (iFile.is_open()) { while (!iFile.eof()) { getline(iFile,holdUsername); } } } //This wont execute!, It skips to "enter selection" if (sizeof(holdUsername) < 2) { cout << holdUsername; cout << sizeof(holdUsername); cout << "test"; } //Enter Selection cout << "\n\n Please choose format: 1 = Generic 2 = Specific 3 = Default \n\n Enter Selection now: "; cin >> cselection;