In GTA IV, you have the option to date five women in Liberty City. Each potential date has their own taste in clothes and activities, making each person different. Girlfriends also give a variety of bonuses.
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The basic structure of a date is the same regardless of the girl you are dating.
There are five dateable girls in GTA IV. Two of them are met during the main plotline and three others are met online. You can date as many girls as you like at once and there seem to be no punishments for doing so. It can, however, get hectic keeping five women happy all of which are sending you text messages and calling you.
Michelle is the first girlfriend you have in the game. You meet her when you're set up on a blind date by your cousin Roman and his girlfriend Mallorie. She seems reasonable and normal although she always seems to be suspicious of you, constantly asking if you're involved with criminals. Michelle ceases to be dateable over the course of the game due to a plot twist.
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Kate is in the McCreary family, an Irish criminal family that you work with quite extensively. You're forced into dating her by her brother Packie during the course of the main storyline. Kate most notably will never invite you into her house because she is allegedly saving herself for marriage.
Likes
Kiki is one of the two dateable girls on Love-Meet.com (an in-game dating site). She goes by the name LawChick online, but once you get her number you refer to her as Kiki. She's something of an idealist and is always out to save the world. Like most of the characters in GTA Kiki is a stereotype dramatized to the point of satire.
Once you get to about 80% likeness with Kiki she will call you and let you know that she has some influence with judges. Being an unfairly persecuted immigrant you can call Kiki and have her clear your wanted level. However, this ability does not work on all missions and at higher wanted levels she will tell you that the cops are serious and there's nothing she can do.
Carmen is one of the dateable girls on Love-Meet.com (the other being Kiki.) She goes by the screen name SoBoHoe and is a nurse. Carmen is extremely self-centered and acts as if every date with her is a golden gift from the gods. She also often refers to herself in the third person.
It's unclear precisely how to use this, but after reaching a certain level with Carmen she'll tell you that she can heal you over the phone. Whenever you call her for this she'll give you a basic health tip like "apply pressure to the wound" which heals some of your damage.
Alex is the last girl that can be dated in GTA and can be found on Craplist.com (a mock of Craig's List) under the name LiberatedWoman. She is a rather odd girl always talking about her online friends and her blog whenever you're on a date and lamenting how hard her life is with her father paying for everything.
Being as stylish as she is Alex is able to get you discounts at clothing stores if you call her up before you make a purchase. Not a particularly useful ability, but it's appreciated.