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Emma, tired of pining after a married man and being alone, starts dating football coach Ken, whom she doesn't even like in a romantic way. Despite her engagement and Will's marriage, their feelings for one another do not disappear.

Will discovers his wife's fake pregnancy and he leaves her stating that he doesn't feel the same for her as he once did.

Will states that he may not be willing to back off of Emma, but eventually he and Carl come to an agreement: Will will leave Emma and Carl's relationship alone, but if Emma starts 'leaning Will's way' again, he will go after her.They do begin to date, and Emma even tries to push aside her mysophobia to try to become intimate with Will.She is still uncomfortable with intimacy, and she admits to Will that he is the first guy she has let get that close to her sexually.Will has strong feelings for Emma, which most likely result to his failing marriage and, and from her listening to his problems and giving him advice when he needed it the most.The two have moments where their sexual tension and attraction to one another are strongly evident, but both have to hold back their feelings because Will was married and his wife, Terri, is pregnant.In Season Three, they get engaged in Yes/No, and in Nationals, they have sex for the first time, where Emma loses her virginity to Will.

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