When Lola advances to a regional pageant, she worries she could lose for the first time.
At the elementary school, Lola is competing in the Little Miss Royal Woods pageant. As she competes, Lincoln shows off how his advice is beneficial to her success. Once the pageant is finished, Lola is announced as the winner. As the family begins to congratulate Lola on another successful win, Cheryl tells Lola that she has been invited to Little Miss Southeastern Michigan pageant this upcoming weekend. Lola is overwhelmed by this news, since she's never competed in a pageant of that level before. Unfortunately, Rita and Lynn Sr. will be occupied during the weekend, so they enlist Lori to chaperone for Lola. Lori declines at first, but she relents when her parents decide to throw in a spa package.
The next day, Lori and Lola arrive at the Caribou Suites in southeast Michigan to check in. As they wait, Lola meets the other pageant contestants. There's Chinah, who has won the most titles before the age of 7, Jackie, who stars in toothpaste commercials, and Claudette, whose gowns are all made in Paris. Realizing how tough her competition will be, Lola nervously excuses herself so she can get ready for rehearsals.
Upon arriving to the practice hall, Lori decides to use her spa package, but the spa turns out to be packed (up to the point where the spa's worst masseuse is taken). During rehearsals, Lola is clearly awestruck at how much more talented and smarter the other pageant contestants are, making her ditch practice and head back to the hotel room she and Lori are staying in. Excusing herself to the bathroom, Lola calls up Lincoln and explains her dilemma with the other contestants as well as her fear that she could lose for the first time in her entire career. Lincoln, however, explains that Lola is not going to lose, and he advises her to get some sleep so that she won't look like a mess the next day. After hanging up, Lola suddenly gets an idea.
The next day, Lori wakes up and discovers Lola looking really sick. Seeing how Lola needs to skip out on the pageant, Lori decides to spend her day with Lola as she gets better, spending her money on necessities, such as "Get Well" balloons, flowers, mani pedi products (the fancy kind), and cookies that cost over $5. Eventually, while pretending to be in a pageant, Lola breaks down crying. When Lori asks what's wrong, Lola says that she's not really sick. She explains that she faked being ill just to avoid competing in the pageant out of fear that she'll lose. Lori immediately feels sympathetic towards Lola, as she reminisces about how she almost skipped out going to homecoming out of fear that she wouldn't win homecoming queen. But after sucking it up, Lori went anyway. She did lose the title of homecoming queen to Carol Pingrey, and she admits that it stung. Even so, she tells Lola that if she didn't go to the dance, she would've missed out on a wonderful experience. Lola realizes that as she gets older, the competition will get harder, but that shouldn't stop her from doing what she loves. Inspired by Lori's words, Lola decides that she wants to compete in the pageant. However, she feels that she can't in her current condition coupled with the fact that the pageant starts in ten minutes. Lori calls up Lincoln, since he knows how to fix up Lola in a short amount of time.
The pageant begins, and Lola, with encouragement from Lincoln (via video chat) and Lori, presents her stuff with great joy. At the end of the night, the emcee announces the winners: Claudette and Jackie are the runner-ups, and Chinah is crowned Little Miss Southeastern Michigan. With the pageant complete, Lola admits that even though she lost, she’s glad that she did what she loved (even Jackie commends her for a great job, as well as stating that she and the others will have to look out for her next year). With that mind, Lori decides to take Lola to the spa for some "well-deserved pampering."