Random Will Smith Girlfriends on Fresh Prince (20 items)

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  (#1) Lisa Wilkes

  • The Fresh Prince of Bel-Air

  Fun fact: Jada Pinkett-Smith, Will Smith's wife in real life, was originally supposed to play Lisa Wilkes, but she was too short. In stepped Nia Long, who starred as Will Smith's girlfriend-turned-fiancé, Lisa Wilkes. 

  Lisa is the girl who comes in and "tames" Will; he reforms from his womanizing ways to be with her. Their relationship makes Will believe in monogamy and true love for the first time, and he proposes. They almost get married twice - once in Vegas, and once at a planned ceremony - but they both realize that they have too many doubts to go through with it. 

  In earlier episodes, such as season two's "She Ain't Heavy," Long played the role of Claudia. When Long was selected to play Lisa Wilkes later on in the series, the character of Claudia was replaced by Raven-Symoné.
  
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  (#2) Jackie Ames

  Tyra Banks played the lovely Jackie Ames, one of Will's recurring friends on the show. Jackie and Will grew up together in West Philadelphia, and they haven't seen one another in three years.

  Initially, Jackie is upset because Will hasn't called her in so long, but she eventually forgives him when she learns that he didn't call because he missed her too much. Jackie moves out to LA on a basketball scholarship for the University of Los Angeles. She gets a job at the campus store, the Peacock Stop, and hires Will to be one of her employees. Will reveals that he and Jackie once hooked up back in Philly, but Jackie maintains that they are still just friends.
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  (#3) Elise Neal as Wendy

  In the season four episode "M Is for the Many Things She Gave Me," Elise Neal plays Wendy, the daughter of one of Uncle Phil's ex-girlfriends. She and Will hit it off, until Will is seduced by her mother, Janice.
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  (#4) Vanessa L. Williams as Danny Mitchell

  In season three, Uncle Phil has to back out of taking a pregnant Vivian to Lamaze class. Will reluctantly agrees to step in as Vivian's breathing coach, and the two head off to Lamaze.

  During the class, Will hits it off with Danny Mitchell (played by Vanessa L. Williams), a pregnant sportscaster who invites Will to a game with him. Their day out takes a turn when Danny unexpectedly goes into labor.
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  (#5) Lela Rochon as Cindy Norris

  In season two, Will secretly starts working at a pirate-themed restaurant in order to save up money to go to the school dance with Cindy Norris, played by Lela Rochon. Uncle Phil offers to pay for him, but Will doesn't want to end up as spoiled as Carlton. In the end, Uncle Phil realizes that there's nothing wrong with a little hard work, and Will realizes that there's nothing wrong with accepting help from your family on your way to success.
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  (#6) Garcelle Beauvais as Sandra

  Garcelle Beauvais plays Sandra in season six, one of the two beautiful women that Will and Carlton take out on a double date. When they go back to the girls' apartment, Will and Carlton are in for a nasty surprise when they find out that one of them has a boyfriend... and he's huge! Fearing for their lives, the boys are forced out the window and onto the fire escape, where they have to be rescued by a crisis intervention team.
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  (#7) Mimi Mumford

  Victoria Rowell starred as Mimi Mumford in the season one episode "Clubba Hubba." Will is enchanted and fascinated by Mimi, but he needs to impress her father before he can take her out on a date. Uncle Phil, Carlton, and Geoffrey do their best to teach Will how to be a gentlemen, using My Fair Lady as their inspiration. Although Will manages to bamboozle Mr. Mumford by pretending to be Kipp Smithers, a high-class preppy kind of guy, his plan backfires, when he realizes that Mimi would rather date a bad boy "from the hood."

  Will exhausts himself switching back and forth between classy Kipp and hardcore Will. He eventually realizes that he'd rather be himself than be accepted by Mimi Mumford and her dad. 
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  (#8) Amy Hunter as Samantha

  In season four, Will and his date, Samantha (played by Amy Hunter), go on a double date with Ashley and her new boyfriend. When Ashley and her guy take off, Will becomes very overprotective of Ashley, and ruins everything. Samantha ends up leaving will because of his "double standards." 
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  (#9) Mari Morrow as Will's Prom Date

  Mari Morrow plays Will's prom date in the season three episode "Just Say Yo," in which Carlton accidentally overdoses on amphetamines from Will's locker.
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  (#10) Vivica A. Fox as Janet

  In the season one episode "It Had to Be You," Vivica A. Fox stars as Janet, the sister of DJ Jazzy Jeff. Jazz tries to fix his sister up with Will, and Will initially refuses - that is, until he sees how gorgeous she is. He agrees to take her out on a date, but is turned off by her controlling nature. Janet already has their whole life together planned out before their first date is even underway.

  Will's only plan is to pawn her off on Carlton, who stands up to Janet, causing her to fall in love with him. 
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  (#11) Queen Latifah as Marissa Redman

  When Hilary lands a new job in season one, as the assistant to actress Marissa Redman (Queen Latifah),  she doesn't quite know what she's in for. Marissa is obnoxious, demanding, and overbearing as a boss - she even threatens to fire Hilary if she can't score a date with Will! Fearing for her job, Hilary sets Will and Marissa up on a blind date. Will agrees, but only if Jazz can come along with him as Hilary's date. The four embark on a double date that ends abruptly when Marissa's temper gets the best of her. Hilary quits on the spot, and the gang goes home, leaving Marissa alone in the restaurant to brood.

  Queen Latifah also played DeeDee, a heavier girl than Will is used to dating, in season two. Will and DeeDee really hit it off - they have everything in common, except for one thing: Will isn't used to dating a girl as curvy as DeeDee. Her weight stops him from asking her to the school dance, because his friends are making fun of him for dating a full-figured girl. When Will sees DeeDee dancing with another guy, he realizes that what's on the inside is way more important than a couple of extra pounds.
  
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  (#12) Kayla Samuels

  Vivian invites one of her students to dinner in the season one episode "Love at First Fight." Will tries to impress Kayla Samuels, played by Jasmine Guy, by comparing their common backstories. Kayla is completely turned off, and Will is bummed out because he failed to pick her up.

  The next time she comes over, Will and Kayla engage in an epic "Yo Mama" joke battle, and start to like each other. They end up dating, until Aunt Vivian notices that Kayla's grades begin to slip. She has a heart-to-heart with Kayla, and reveals her own personal struggle with boys and success.
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  (#13) Naomi Campbell as Helen

  When Geoffrey's birthday rolls around, in season one's "Kiss My Butler," Will knows just what to get him: a blind date with Ashley's friend's nanny, Helen, played by the gorgeous Naomi Campbell. What Will doesn't know is that Helen is exactly his type! The two hit it off at Geoffrey's birthday party, and Geoffrey ends up giving Helen's number to Will so that he can ask her out instead.
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  (#14) Kim Fields as Monique

  In season three, Will is ready to go all the way with his new girlfriend, Monique, played by Kim Fields. Monique, however, is an old-fashioned girl, and wants to wait until marriage to lose her virginity. Will and Jazz set up a crazy scheme to trick Monique into thinking that she and Will are married. In the end, Will backs out of it because his conscience gets the better of him.
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  (#15) Tisha Campbell-Martin as Kathleen

  In the first episode of season two, Will experiences his first California earthquake while he and his girlfriend, Kathleen (Tisha Campbell-Martin), are trapped in the basement. Uncle Phil and Vivian think that Will and Kathleen are moving too fast for their new relationship, until Will discovers who Kathleen really is during their time stuck in the basement.

  They realize that they aren't compatible together as a couple, and end up going their separate ways.
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  (#16) Michelle Michaels

  Stacey Dash plays celebrity superstar Michelle Michaels in season four. Will meets Michelle when she shows up on his college campus for a tour. The two of them date, but their relationship is more of just a fling for Michelle, who is constantly in the spotlight and not really ready to settle down. Will realizes that he'd rather have a more meaningful relationship with someone else, than what Michelle can give him.
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  (#17) Galyn Görg as Helena

  When Uncle Phil signs up the family for a gym membership at a health club in season six, Will has no idea what he's in for. Inspired to take boxing lessons, Will enters the ring with Helena, a gorgeous boxing instructor played by Galyn Görg. Helena totally kicks Will's ass, and Will learns a humbling lesson about female strength.
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  (#18) Robin Givens as Denise

  In season five, Will meets Denise (Robin Givens), a gorgeous (albeit over-zealous) girl at his college. Denise seems determined to win Will's heart. The only problem? Will is engaged to Lisa! He gets cold feet, and almost gives in to Denise, but changes his mind at the last minute in order to remain faithful to Lisa.
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  (#19) Pam Grier as Janice

  In season four, Vivian is upset when Uncle Phil's ex-girlfriend, Janice (played by Pam Grier), comes to visit. Uncle Phil lets it slip that he "settled" for Vivian after he and Janice broke up, and Vivian is furious. Will is supposed to be getting to know Janice's daughter, Wendy, but ends up being seduced by Janet instead.

  When Uncle Phil finds out that Janice slept with Will, he apologizes to Vivian, and realizes that he made a huge mistake in flirting with his former fling.
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  (#20) Michole Briana White as Lindsey

  Will starts dating a plain-Jane girl named Lindsey, played by Michole Briana White, in season three. Lindsey keeps lavishing expensive gifts on Will - everything from Lakers tickets to a motorcycle. Will isn't really into Lindsay, but he can't say no to all the gifts. In the end, it is revealed that Lindsay doesn't really like him either; she only wanted him because he's the star on the basketball team, and other girls are after him.

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