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Wait till he comes out and go back to Roman's working place. You should receive a message, read it and go back to Roman again. Park on the yellow spot and honk (push left analogue stick).
Drive her to her house and answer the call from Roman. Go to the Russian shop and buy something more civilized.
When you do so, have on a completely new outfit, pick her up in Roman's Taxi, and take her to eat.
When you get back, you'll have the option to say goodbye or ask if you can come up. She should say yes, and you get the achievement after a sweet little cutscene. If you go to the internet post-campaign and meet up with... Anyway, her real name is Carmen, and you just date her until she says yes to you on something like the third date.
Go to the R on the map and enter the basketball field. Move close to him and take his knife (dodge and punch). Take the Roman's cab and go pick up Jermaine at Rotterdan Hill.
Kick few asses and go back to car as fast as possible.
How much they like you is based on several factors, such as the car you're driving, where you purchased your clothes, and where you take her.
Hide behind the sofa and shoot the two remaining guys.
Go upstairs - in this room you can save your game, change clothes or just watch the TV. When you're done parking your car (1) Roman will ask you for a favor. Loan sharks want their money back so Roman isn't too keen on meeting them. When you see two guys walking into the shop, call Roman immediately.
Learn how to drive and go there with the help of GPS. Reward 25$ Give Roman a lift to his work and then follow the GPS.
**Can be done after completing story mode** Name: Michelle Acquired: Complete "Three's a Crowd" Favorite Cars: Roman's Cab, Merit, Voodoo, Banshee, Blista Favorite Clothiers: Russian, Hats, Glasses Favorite Venues: Darts (80%), Pool (80%), Comedy (75%), Steinway Beer Gardens (70%), Lucky Winkles (70%) Name: Carmen Ortiz Acquired: Date "So Bo Hoe" from after completing "Out of the Closet" Favorite Cars: Sultan RS, Dukes, Stallion, FXT, E109 Favorite Clothiers: Modo, Perseus Favorite Venues: Any Drinking/Club (90%), Darts (80%), Strip Club (80%), Cabaret/Comedy (80%) Special Ability: Can heal you when you're injured by calling her Name: Kiki Jenkins Acquired: Date "Law Chick" from after completing "Out of the Closet," and unlocking the island of Algonquin Favorite Cars: Washington, Chavos, Dilettante, Marbella, Willard Favorite Clothiers: Russian, Hats, Glasses Favorite Venues: Jerkov's (85%), Club Liberty (85%), Pool/Dart/Bowling (80%), Cabaret/Comedy (80%) Special Ability: Can get rid of up to a 3 star wanted level by calling her Name: Alexandra Chilton Acquired: Date "Liberated Woman" from after completing "Out of the Closet," and unlocking the island of Algonquin Favorite Cars: Huntly, Turismo, Stretch, Infernus, Cognoscenti Favorite Clothiers: Perseus Favorite Venues: Pool/Dart/Bowling/Strip Club (80%), Cabaret/Comedy (80%), Steinway Beer Gardens (70%), Lucky Winkles (70%) Special Ability: You will get all clothes in the city for half price for 24 in-game hours after she offers it to you Name: Kate Mc Reary Acquired: Complete "Waste Not Want Knots" Favorite Cars: Rebla, Patriot, Comet, Habanero, Super GT Favorite Clothiers: Russian Favorite Venues: Darts (80%), Pool (80%), Steinway Beer Gardens (70%), Lucky Winkles (70%) This can be a very simple achievement if you know what to do.
After the "First Date" mission, you have the option to call Michelle and arrange another date.