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.
Conversely though, Niko's choice of wardrobe and vehicular transport will also affect whether or not his date has a good time.
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.
Whilst limitations with the Xbox One now appear to have been resolved, problems with online purchases and some app functionality continue for 360 users.