I am not sure that it will work in all cases. But I think it might be a solution.
left_df = pd.DataFrame({'left_dt': ['2014-08-23 07:57:03.827516',
'2014-08-23 09:27:12.831126',
'2014-08-23 11:55:27.551029',
'2014-08-23 16:11:33.511049'],
'left_flag': [True, False, True, True]})
left_df['left_dt'] = pd.to_datetime(left_df['left_dt'])
right_df = pd.DataFrame(
{'right_dt': ['2014-08-23 07:12:52.80587', '2014-08-23 15:12:34.815087'],
'right_flag': [True, True]})
right_df['right_dt'] = pd.to_datetime(right_df['right_dt'])
left_df.set_index('left_dt', drop=False, inplace=True)
right_df.set_index('right_dt', drop=False, inplace=True)
output_df = left_df.join(right_df, how='outer').sort_index()
output_df.fillna(method='ffill', inplace=True)
output_df.dropna(subset=['left_dt'], inplace=True)
output_df['diff'] = abs(output_df['left_dt'] - output_df['right_dt'])
output_df.sort(columns='diff', inplace=True)
output_df.drop_duplicates(subset=['left_dt'], inplace=True)
output_df.sort_index(inplace=True)
output_df = output_df.reset_index(drop=True)
output_df.drop('diff', axis=1, inplace=True)
output_df
left_dt left_flag right_dt right_flag
0 2014-08-23 07:57:03.827516 True 2014-08-23 07:12:52.805870 True
1 2014-08-23 09:27:12.831126 False 2014-08-23 07:12:52.805870 True
2 2014-08-23 11:55:27.551029 True 2014-08-23 15:12:34.815087 True
3 2014-08-23 16:11:33.511049 True 2014-08-23 15:12:34.815087 True
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