After requesting a date, you'll have to wait awhile (a week or more) for a reply. Reply to the e-mail to trigger the appointment, and be sure to show up on time.
After the initial date, you can then collect the girl's phone number so you can call and set up additional dates.
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.
This feature is available after the “Out of the Closet” mission in Brucie's mission line.
As with friends, each girl is only awake for a certain number of hours, and calling them while they're sleeping or busy will negatively affect the relationship.
After a couple of successful outings, “try your luck” when dropping the date off and if she accepts you will later get a phone call from her, unlocking the special ability. Her online username is “Law Chick.” Kiki is quite easy to please; she prefers clothes from the Russian shop and downscale cars. Special Ability: Lower Wanted Level - Call Kiki to have her lower your current wanted level by three stars.
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.
She seems to like flashy clothes (from Perseus) and mid-level cars.
Do not wear anything from the Russian clothes shop.
Since Kate and Michelle are fairly easy to please and only pertain to the storyline, they won't be covered here.
There are three other girls that Niko can meet and date via the
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.