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Dating these girls is not a requirement to attain the 100% game completion stat, however each has a special ability that is unlocked once they like you enough.
Both Michelle and Kate like Niko for who he is, so wearing something upscale (i.e., anything not from the Russian clothes store) and showing up in a flashy ride is typically to be avoided when dealing with either of them.
Call your friend and perform activities with him on a regular basis to increase your 'like stat'.
This stat (amongst other friend stats) can be accessed from the pause menu under the 'Stats' section.
As you progress through the story, Niko will be able to wine and dine with a number of Liberty City women.
Dating is much like hanging out with friends in that each girl has their own preferable activities.