i got an issue over ranking of date times. Lets say i have following table.
ID TIME
01 2018-07-11 11:12:20
01 2018-07-12 12:00:23
01 2018-07-13 1
For me working convert column to datetimes for avoid your error.
data['TIME'] = pd.to_datetime(data['TIME'])
data['RANK'] = data.groupby('ID')['TIME'].rank(ascending=True)
print (data)
ID TIME RANK
0 1 2018-07-11 11:12:20 1.0
1 1 2018-07-12 12:00:23 2.0
2 1 2018-07-13 12:00:00 3.0
3 2 2019-09-11 11:00:00 1.0
4 2 2019-09-12 12:00:00 2.0