About me: On her initial introduction, Sherry is shown to be a weary yet kind-hearted individual, looking out for her friends (such as Amber and Mark) and trying her best to maintain the peace. She also appeared to be invested in the emotional well-being of those around her, as seen when she comforted Mark over Amber's disappearance.
Following the end of the war between the joint communities and the Saviors, however, Sherry's true personality gradually starts to surface. Even though she was free of Negan, Sherry left Dwight for another man once more, greatly attributing to his self-doubt that ultimately caused him to resign as leader of the Saviors. Though Dwight initially believed Sherry became one of Negan's wives to better both of their lives, it is implied she only did this for her benefit. Negan also describes Sherry as an opportunist, a sentiment that is reinforced in Here's Negan, where it is implied she started her affair with Negan much sooner than previously thought. As leader, she starts exhibiting signs of megalomania, partially caused by being forced to submit to Negan.
Sherry is introduced to Negan by Dwight. She initially distrusts him but gradually warms up to him, as evidenced by her flirting with Negan.
Life at the Sanctuary
At some point after the Saviors discover the Sanctuary, Sherry agrees to become one of Negan's wives (being the first one to do so), with the justification that it would make life easier for herself and her husband, Dwight. However, she underestimated how much she would miss him after the separation, so the two continued to have an affair behind Negan's back. After Negan found out, he presumably gave her the same offer he would later give to Amber: going back to Dwight or staying with Negan. Sherry chose the latter, resulting in Dwight being punished by having his face burnt with an iron. She later convinced Amber to become one of Negan's wives as well.
What Comes After
Sherry is first seen comforting Amber, and tries to help her by telling Negan to go easy on her. She is seen also in the area where Mark is being tortured. She attempts to talk to Dwight, but, is angrily rebuffed by him.