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They went to the dance together and were shown to have crushes on each other.
Addison and Woody flirt with each other in cooking class, even though for the most part, she seems to be crushing on Cody, their cooking class substitute teacher, along with all the other girls in the class (except for Bailey, since she is already his girlfriend). This upsets both Woody and Bailey, and they try to come up with a plan to win back their "gal" (for Woody) and "guy" (for Bailey).
They go on a date after setting it up through the game Better Life. They nearly kiss at the end, but Mr. Blanket throws ping-pong balls at them, interrupting the kiss.
While selecting partners for a class project on marriage, They 'marry' each other for class. Woody gives Addison a Ring Pop for each finger in order to get her to 'marry' him. Woody is shown to not want to have children, while Addison wants tons.
Woody is feeling awful because he has never kissed a girl, and hopes that Addison will be his first. When he tries to ask her out to Prom, he cannot do it because he is afraid that she will reject him if he is a bad kisser. Cody helps him out by teaching him how to kiss a ham, but as he is doing that, Addison walks up to his door and overhears him kissing the ham, but thinks its another girls, and then walks away distaught. After that Woody tries to ask her to Prom, but she angrily refuses, which frustrates Woody because he does not know why she is acting this way. Eventually, Prom comes and Woody arrives to see Addison dancing by herself. After a little motivation from Cody, Woody manages to ask Addison why she is so mad. Once he finds out that she overheard him "kissing another girl," Woody tells her what really happened, and that he did it for her. She then forgives him. They then "go to prom together" (even though they are already there) and share their first kiss.