Dating girlfriends is a popular pastime in Grand Theft Auto IV. Two of the girlfriends are introduced during the storyline. The other three are found online from in-game dating websites, such as LoveMeet.net or CrapList.net. Aside from the comic relief of these relationships, increasing the fondness of girlfriends unlocks their "special abilities," which can help in difficult missions late in the game. Carmen, for example, is a nurse who can be contacted for a health boost, while Kiki is a lawyer who can remove your wanted level.

Favor and fondness are gained by taking the girls to different city venues. For a date to be deemed successful, Niko must cater to the women's clothing and vehicle taste, as well as the level of fanciness she prefers. Achieving 100% fondness with all five girlfriends is not necessary to achieve 100% completion of the game.

Michelle is introduced to Niko by Mallorie Bardas during Three's a Crowd. Niko is advised by Mallorie to purchase new clothes from the Russian clothing store to impress her. After that, he calls to schedule a date. On her dates, do not crash your car or Michelle will not invite you in after a date.

Michelle prefers Russian clothes and likes all vehicles except police cars, trucks, and beaters. She prefers most venues, particularly bowling, darts, pool, the Burger Shot restaurant, diners, and the Cluckin' Bell restaurant. You need to attain 100% fondness before The Snow Storm mission because you will not be able to contact her after that.

Kate McReary is introduced to Niko during the Harboring a Grudge mission. Patrick McReary suggests a date after they complete the Waste Not Want Knots mission. Kate prefers Modo clothing and nice shoes. She likes moderate cars that are not too fancy but not too cheap. Kate prefers going out to play darts, shoot pool, and going to the Steinway Beer Garden. She will not invite you in for "coffee" after any date. 100% fondness needs to be attained before the Mr. and Mrs. Bellic mission because she is killed during that mission.