import datetime data = """01:35:01 0.90 0.99 0.90 01:40:01 0.53 0.78 0.85 01:45:01 0.42 0.67 0.81 08:20:01 0.58 0.95 0.93 08:25:01 0.74 0.65 0.79 08:30:01 0.40 0.50 0.69""" gap_delta = datetime.timedelta(hours=1) prev_time = datetime.datetime.strptime(data[:8], "%H:%M:%S") for line in data.splitlines(): time_string = line[:8] next_time = datetime.datetime.strptime(time_string, "%H:%M:%S") if (next_time - prev_time) > gap_delta: print "gap" print time_string prev_time = next_time