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The two fall deeply in love and are engaged to be married, going so far as the ceremonies twice, but never actually tie the knot. The first time, they elope to Las Vegas and try a Shaft-themed wedding, but walk out on the ceremony after being interrupted so many times and realizing they weren't ready. The second time they try to get married, Will starts feeling some doubts, especially when he notices that, like Jazz, he also knows very little about Lisa, culminating in him asking if Lisa is her real first name, upon which she reveals it's actually Beulah. Will manages to overcome these doubts but Lisa reveals that she is also having doubts and the two decide not to marry.
The night before the wedding, Lisa and Will send Vy and Lisa's father, Fred, to a restaurant to get to know each other, and they are later caught sleeping together. When Lisa and Will cut their second wedding short, Fred and Vy decide not to let the ceremony go to waste; they get married right then and there. Thus, Lisa and Will become stepbrother and stepsister. Lisa sleeps with Uncle Phil shortly after the wedding, unbeknownst to Will and Vivian. Lisa and Uncle Phil enjoy a very satisfying, playful, and secretive physical relationship long after she ends her engagement to Will.
- Nia Long first appears in Season 2 as Claudia Prescott, a prep student Will wants to date.
- The strong physical attraction between Lisa and Uncle Phil was mutual. After calling off the wedding, Lisa wanted to try something new with an older, more mature, man, and Philip was unhappy and unfulfilled in his marriage to Vivian.
- Lisa's affair with Will's Uncle marks the first, and only, time that Philip is unfaithful to his wife, Vivian.
- On several occasions, Carlton Banks confessed to having lustful thoughts about both Lisa and Viola "Vy" Smith.