You want to split with at least 1 whitespace followed with a date like pattern, thus, you may use
re.split(r'\s+(?=\d{2}(?:\d{2})?-\d{1,2}-\d{1,2}\b)', s)
See the regex demo
Details
\s+ - 1+ whitespace chars
(?=\d{2}(?:\d{2})?-\d{1,2}-\d{1,2}\b) - a positive lookahead that makes sure, that immediately to the left of the current location, there are
\d{2}(?:\d{2})? - 2 or 4 digits
- - a hyphen
\d{1,2} - 1 or 2 digits
-\d{1,2} - again a hyphen and 1 or 2 digits
\b - a word boundary (if not necessary, remove it, or replace with (?!\d) in case you may have dates glued to letters or other text)
Python demo:
import re
rex = r"\s+(?=\d{2}(?:\d{2})?-\d{1,2}-\d{1,2}\b)"
s = "2018-03-14 06:08:18, he went on 2018-03-15 06:08:18, lets play"
print(re.split(rex, s))
# => ['2018-03-14 06:08:18, he went on', '2018-03-15 06:08:18, lets play']
NOTE If there can be no whitespace before the date, in Python 3.7 and newer you may use r"\s*(?=\d{2}(?:\d{2})?-\d{1,2}-\d{1,2}\b)" (note the * quantifier with \s* that will allow zero-length matches). For older versions, you will need to use a solution as @blhsing suggests or install PyPi regex module and use r"(?V1)\s*(?=\d{2}(?:\d{2})?-\d{1,2}-\d{1,2}\b)" with regex.split.
r'\s+(?=(?:(?:20)?[01]?[0-9])-(?:1[0-2]|0?[0-9])-(?:[0-2]?[0-9]|3[01]))'with split.