The first girlfriend you will encounter is Michelle. After the Roman mission Three's a Crowd you can call her and ask her out on a date. This will trigger a Michelle mission called First Date in which you have to drive her to the amusement park on Firefly Island and take her bowling. Drive her home after the bowling to complete the mission. Now you can start dating Michelle.

When you want to take out a girl on a date, you call her on your phone and asks if she want to go out. Or the girl can call you asking the same thing. Take the girl to a place she likes to make the date a success. Also, make sure you wear clothes she likes and pick her up in a car she likes to make the date a succes.

You can have more than one girlfriend at the same time, with a total of up to four girlfriends. If you date a girls from the internet, you have to have a Like stat higher than 60% to get her number after the date. After you sleep with one of the Internet girls for the first time, you will unlock a special ability. The special ability can be used three times before you have to take her out on a date again.

Girlfriends available:

Michelle

Requirements to unlock:
Complete the Roman mission Three's a Crowd.
Complete the Michelle mission First Date.

Likes:
Cars: Taxi, Merit, Blista, Voodoo, Banshee.
Clothes: Russian, Hats, Glasses.
Drinking: Lucky Winkles, Steinway Beer Garden.
Food: Pizza, Diners.
Activity: Darts, Pool, Bowling.
Shows: Comedy.

Dislikes:
Cars: Solair, Uranus, Fortune, Futo, Primo.
Clothes: Modo, Perseus.
Drinking: Jerkov's, Club Liberty, Comrades Bar.
Food: Mr. Fuk's Rice Box, Superstar Café, Cluckin' Bell, Burger Shot.
Activity: Strip Club.
Shows: Cabaret.

Carmen Ortiz (SoBoHoe)

Requirements to unlock:
Complete the Brucie mission Out of the Closet.
Make contact online at Love-meet.net.

Availability hours:
01:00 pm to 06.00 am

Special Ability:
Boosts your health.

Likes:
Cars: Stallion, FXT, Dukes, Sultan RS, E109.
Clothes: Modo, Persus.
Drinking: Comrades Bar, Lucky Winkles, Club Liberty, Jerkov's, Steinway Beer Garden.
Food: Pizza, Diners.
Activity: Darts, Bowling, Strip Club, Pool.
Shows: Cabaret, Comedy.

Dislikes:
Cars: Merit, Minivan, Dillettante, Marbella, Stratum.
Clothes: Hats, Glasses, Russian.
Drinking: -
Food: Cluckin' Bell, Burger Shot, Superstar Café, Mr. Fuk's Rice box.
Activity: -
Shows: -

Alexandra Chilton (Liberated Woman)

Requirements to unlock:
Complete the Brucie mission Out of the Closet.
Make contact online at Craplist.net.

Availability hours:
06:00 am to 02.00 am

Special Ability:
50% discount on clothes in all shops.

Likes:
Cars: Infernus, huntley, Turismo, Cognoscenti.
Clothes: Persus.
Drinking: Steinway Beer garden, Lucky Winkles.
Food: Pizza, Diners.
Activity: Bowling, Pool, Darts, Strip Club.
Shows: Cabaret, Comedy.

Dislikes:
Cars: Bobcat, Pony, Willard, Dukes, Emperor.
Clothes: Modo, Russian.
Drinking: Comrades Bar, Jerkov's, Club Liberty.
Food: Cluckin' Bell, Burger Shot, Superstar Café, Mr. Fuk's Rice box.
Activity: -
Shows: -

Kiki Jenkins (LawChick)

Requirements to unlock:
Complete the Brucie mission Out of the Closet.
Make contact online at Love-meet.net.

Availability hours:
06:00 am to 02.00 am

Special Ability:
Removes a Wanted Level of up to three stars.

Likes:
Cars: Chavos, Dillettante, Marbella, Willard, Washington.
Clothes: Russian, Hats, Glasses.
Drinking: Jerkov's, Club Liberty, Lucky Winkles, Steinway Beer Garden.
Food: Cluckin' Bell, Burger Shot, Pizza, Diners, Superstar Café, Mr. Fuk's Rice box.
Activity: Bowling, Pool, Darts.
Shows: Cabaret, Comedy.

Dislikes:
Cars: Sabre GT, Super GT, Infernus, Turismo, Coquette.
Clothes: Modo, Perseus.
Drinking: Comrades Bar.
Food: -
Activity: Strip Club.
Shows: -

Kate Mcreary

Requirements to unlock:
Complete the Packie mission Waste Not Want Knot.

Availability hours:
08:00 am to 12.00 am

Likes:
Cars: Super GT, habanero, Comet, Rebla, Patriot.
Clothes: Russian.
Drinking: Steinway Beer Garden, Lucky Winkles.
Food: Pizza, Diners.
Activity: Darts, Pool.
Shows: -

Dislikes:
Cars: Voodoo, Solair, Stretch, Moonbeam, Sultan RS, Peyote.
Clothes: Modo, perseus, Hats, Glasses.
Drinking: Club Liberty, Jerkov's, Comrades Bar.
Food: Cluckin' Bell, Burger Shot, Mr. Fuk's Rice Box, Superstar Café.
Activity: Strip Club, Bowling.
Shows: Cabaret, Comedy.