Convert both strings to timestamps (in your chosen resolution, e.g. milliseconds, seconds, hours, days, whatever), subtract the earlier from the later, multiply your random number (assuming it is distributed in the range [0, 1]) with that difference, and add again to the earlier one. Convert the timestamp back to date string and you have a random time in that range.
Python example (output is almost in the format you specified, other than 0 padding - blame the American time format conventions):
import random
import time
def strTimeProp(start, end, format, prop):
"""Get a time at a proportion of a range of two formatted times.
start and end should be strings specifying times formated in the
given format (strftime-style), giving an interval [start, end].
prop specifies how a proportion of the interval to be taken after
start. The returned time will be in the specified format.
"""
stime = time.mktime(time.strptime(start, format))
etime = time.mktime(time.strptime(end, format))
ptime = stime + prop * (etime - stime)
return time.strftime(format, time.localtime(ptime))
def randomDate(start, end, prop):
return strTimeProp(start, end, '%m/%d/%Y %I:%M %p', prop)
print randomDate("1/1/2008 1:30 PM", "1/1/2009 4:50 AM", random.random())