import numpy as np
import pandas as pd
from pandas.io.parsers import StringIO

def find_closest_date(timepoint, time_series, add_time_delta_column=True):
   # takes a pd.Timestamp() instance and a pd.Series with dates in it
   # calcs the delta between `timepoint` and each date in `time_series`
   # returns the closest date and optionally the number of days in its time delta
   deltas = np.abs(time_series - timepoint)
   idx_closest_date = np.argmin(deltas)
   res = {"closest_date": time_series.ix[idx_closest_date]}
   idx = ['closest_date']
   if add_time_delta_column:
      res["closest_delta"] = deltas[idx_closest_date]
      idx.append('closest_delta')
   return pd.Series(res, index=idx)


a = """timestamp,email,subject
2016-07-01 10:17:00,a@gmail.com,subject3
2016-07-01 02:01:02,a@gmail.com,welcome
2016-07-01 14:45:04,a@gmail.com,subject3
2016-07-01 08:14:02,a@gmail.com,subject2
2016-07-01 16:26:35,a@gmail.com,subject4
2016-07-01 10:17:00,b@gmail.com,subject3
2016-07-01 02:01:02,b@gmail.com,welcome
2016-07-01 14:45:04,b@gmail.com,subject3
2016-07-01 08:14:02,b@gmail.com,subject2
2016-07-01 16:26:35,b@gmail.com,subject4
"""

b = """timestamp,email,subject,clicks,var1
2016-07-01 02:01:14,a@gmail.com,welcome,1,1
2016-07-01 08:15:48,a@gmail.com,subject2,2,2
2016-07-01 10:17:39,a@gmail.com,subject3,1,7
2016-07-01 14:46:01,a@gmail.com,subject3,1,2
2016-07-01 16:27:28,a@gmail.com,subject4,1,2
2016-07-01 10:17:05,b@gmail.com,subject3,0,0
2016-07-01 02:01:03,b@gmail.com,welcome,0,0
2016-07-01 14:45:05,b@gmail.com,subject3,0,0
2016-07-01 08:16:00,b@gmail.com,subject2,0,0
2016-07-01 17:00:00,b@gmail.com,subject4,0,0
"""

df1 = pd.read_csv(StringIO(a), parse_dates=['timestamp'])
df2 = pd.read_csv(StringIO(b), parse_dates=['timestamp'])

df1[['closest', 'time_bt_x_and_y']] = df1.timestamp.apply(find_closest_date, args=[df2.timestamp])
df1

df3 = pd.merge(df1, df2, left_on=['closest'], right_on=['timestamp'])

df3
timestamp_x        email   subject             closest  time_bt_x_and_y         timestamp_y  clicks  var1
  2016-07-01 10:17:00  a@gmail.com  subject3 2016-07-01 10:17:05         00:00:05                 NaT     NaN   NaN
  2016-07-01 02:01:02  a@gmail.com   welcome 2016-07-01 02:01:03         00:00:01                 NaT     NaN   NaN
  2016-07-01 14:45:04  a@gmail.com  subject3 2016-07-01 14:45:05         00:00:01                 NaT     NaN   NaN
  2016-07-01 08:14:02  a@gmail.com  subject2 2016-07-01 08:15:48         00:01:46 2016-07-01 08:15:48     2.0   2.0
  2016-07-01 16:26:35  a@gmail.com  subject4 2016-07-01 16:27:28         00:00:53 2016-07-01 16:27:28     1.0   2.0
  2016-07-01 10:17:00  b@gmail.com  subject3 2016-07-01 10:17:05         00:00:05 2016-07-01 10:17:05     0.0   0.0
  2016-07-01 02:01:02  b@gmail.com   welcome 2016-07-01 02:01:03         00:00:01 2016-07-01 02:01:03     0.0   0.0
  2016-07-01 14:45:04  b@gmail.com  subject3 2016-07-01 14:45:05         00:00:01 2016-07-01 14:45:05     0.0   0.0
  2016-07-01 08:14:02  b@gmail.com  subject2 2016-07-01 08:15:48         00:01:46                 NaT     NaN   NaN
  2016-07-01 16:26:35  b@gmail.com  subject4 2016-07-01 16:27:28         00:00:53                 NaT     NaN   NaN

df1.groupby(['email','subject'])['timestamp'].apply(find_closest_date, args=[df1.timestamp])