Sherry’s letter to Dwight on The Walking Dead unravels quite a few mysteries from recent and not-so-recent events with Dwight and with Daryl.
The letter to Dwight from Sherry lets us in on quite a few things about both of those characters in just a few short paragraphs of curly handwriting.
Dwight and Sherry knew each other before the apocalypse. They didn’t find each other after things went bad or at the Sanctuary. Their love goes back a long time.
The way Sherry wrote-in run on thoughts and twisted ideas represents her thinking and the twisted way the world has become. The twisted nature of their relationship once Negan became involved. Even her pretty handwriting represented pretty thoughts amidst a not-so-pretty environment.
How do you love someone when you have to watch them be taken by someone else? And they let themselves be taken so you can stay alive. They are trying to show you they love you be letting themselves be taken. Emotions aren’t that pragmatic.
Sherry doesn’t know what to do to help Dwight. If she stays, she forces him to watch her with Negan. And she watches the man she loves get colder and more separate from the man she knew. Guilt. Loss. Jealousy. Fear. Culpability.
If she goes, he loses her, too. He has lost her either way. Can she do something to help him in the mean time? What would help him? She doesn’t know.
"I wish I could wait for you now but I don’t know if you’d come with me or if you’d take me back there or you’d kill me. You didn’t want to live in that world and I made you. I did what I did because I didn’t want you to die. but now you’ve killed, and you’ve become everything you didn’t want to be, and it’s my fault. You were better than me. Most people are."
Sherry thought Daryl was a reminder of who Dwight used to be. He was looking in the mirror all the time. Letting him go for that reason was a sweet thought, but would it really let him forget?
"I let Daryl go because he reminded you of who you used to be and I wanted to let you forget."
The letter has the potential to affect Dwight in a few ways. He could get colder and more Negan-like without anything to hold on to as far as someone who knew him before the Dwight of the Sanctuary. He may not see that she was trying to set him free.
Or he could realize that she couldn’t take being humiliated in front of him anymore and that she wanted to free him from seeing her with Negan and seeing Daryl as a reminder of who he was and perhaps give him the courage to figure out a way to separate from the Saviors.
If Daryl or Rosita don’t kill him first for killing Denise.