Episode # Episode Title Name Notes
109 Someday Your Prince Will Be in Effect (Part 2) Cindy Will brings her to Hillary's Halloween party. She was never seen again.
110 Kiss My Butler Helen Will gets her number at the end of the episode; we never see the date, but it is implied.
118 The Young and the Restless Tanya Will discusses asking her out with Granny; we never see the date, but it is implied.
119 It Had to Be You Janet Jazz's sister. Will takes her out to dinner twice.
121 Love at First Fight Kayla Samuels One of Aunt Vivian's students.
125 Working it Out Marissa Redman Will goes out with her as a favor to Hillary.
201 Did the Earth Move for You? Kathleen
203 Will Gets a Job Cindy Norris She shows up at the house to go to a basketball game with Will. He spends the whole episode preparing to take her to Homecoming.
208 She Ain't Heavy Denice Williams
208 She Ain't Heavy Claudia Prescott Will takes her to the dance before leaving her for Denice.
211 The Butler Did It Will went on a date with an unnamed woman, playing board games in the kitchen.
222 The Aunt Who Came to Dinner Renee Will and Carlton try to take their respective dates skinny dipping at the end of the episode.
223 Be My Baby Tonight Cynthia Will talks to her on the phone at the beginning of the episode. They make a date for Saturday night that is never mentioned again.
304 P.S. I Love You Lindsey Will goes to the Lakers game and the Autumn dance with her.
309 A Night at the Oprah Latisha Will shouts her name out on Oprah and comes back home to see her.
312 The Cold War Paula Will convinces her to break up with Carlton so he can take her out.
317 Best Laid Plans Monique Will dates her through the whole episode. He fakes a wedding to try to have sex with her.
319 Just Say Yo Cindy Will takes her to the prom.
411 Take My Cousin – Please Rhetta Will takes her to the opera.
414 Sleepless in Bel-Air During the cold open, Will plays saxophone to a woman in the pool house.
417 When You Hit Upon a Star Michelle Michael Will dates the famous singer, ignoring his family for them.
418 Stop Will! In the Name of Love Will intercepts Carlton's date in the cold open.
418 Stop Will! In the Name of Love Samantha Sackin Will takes her on a Valentine's Day double date with Ashley and Ashley's date.
421 The Harder They Fall Lisa Will preps for a movie date with her in the cold open and spends the rest of the episode trying to impress her father.
422 M is for the Many Things She Gave Me Wendy Will takes Janice Robertson's daughter out dancing.
422 M is for the Many Things She Gave Me Janice Robertson Will sleeps with Janice and spends the night.
423 Mother's Day Will is in the middle of a date when Jazz and Jewel arrive.
502 The Client (Part 2) Tisha Will shows up to the studio after a long night with her.
504 Grumpy Young Men Valerie Will goes on a date with her in the poolhouse, but she ends up liking Carlton more.

505, 509, 510, 511, 513, 514, 515, 516, 517, 518, 520, 523, 524, 525

Will's MiseryLove HurtsWill's Up the Dirt RoadWill Steps OutThree's a CrowdIt's a Wonderful LieBullets over Bel-AirA Decent ProposalWill Is From MarsThe Wedding Show (Psyche!)As the Will TurnsCold Feet, Hot BodyLove in an ElevatorFor Whom the Wedding Bells Toll Lisa Wilkes Will dates her over several episodes. They are eventually engaged.
508 Sooooooooul Train Lola She walks Will home. He tells her goodbye in the kitchen. 
511 Will Steps Out Carlotta Will takes her out to spite Lisa.
602 Get a Job Jasmine Perry Will takes her out as part of his Assistant Talent Coordinator responsibilities.
606 Not I Barbecue Sandra Will arrives back at the house after seeing Showgirls with her. Carlton also implies that he has taken seven other women to the same movie. He and Carlton later double with Sandra and her cousin.
612 Boxing Helena Helena Will takes her out after resolving their row at the gym.
613 I, Clownius Lori Williams Will is preparing for a date with her in the cold open.
623 I, Done (Part 1) Will brags about spending time with the woman from the bookstore that Carlton likes.