If your friend calls but you aren't able to hang out, respond positively and then call immediatley afterwards to cancel the activity. There are five different girls which Niko can date, two of which are unlocked automatically during the storyline, and the rest of which are available via the in-game internet.
Call one of the girls to arrange a date, then pick her up within 1 hour (2 real-time minutes) and take her to one of the activities shown on the map.
Don't call her too frequently or her respect for you will drop.
Note that you cannot date a girl when you are on a mission.After a date, you need to wait 5 hours (10 real-time minutes) before calling your girlfriend again.Don't take your friend to an activity that he doesn't like or your 'like stat' will reduce.You can perform upto four activities on each outing in order to give your 'like stat' the highest possible boost.
Each friend (and three of the girlfriends) provide special unlockable abilities in return for maintaining good relationships with them.There are five friends in total, which become available at different times during the storyline.