Chester spends every afternoon at the stage depot so he can prey on any single women that arrive in Dodge City. Doc Adams makes fun of Chester, but the creepy simpleton claims he is only there to pick up the mail for Marshal Dillon.
As soon as the stage arrives, Chester is all over a poor girl named Edna. Edna is played by Patricia Smith, who appeared on Gunsmoke twice. Creepy Chester gets her a room at the Dodge House, and a job with Mr. Jonas at the General Store. Sadly for Chester, he can't seal the deal with Edna, so she is just his friend.
It turns out that the reason Edna has let Chester get close to her is so she could check the U.S. Marshal's Mail every day. Edna has a secret problem. She left the man who wants to marry her, and he is on his way to Dodge City. Meanwhile, insipid Chester continues courting Edna, and trying to be her sunshine and only love. Sadly for goofball Chester, as soon as Edna's true love comes to town, she picks him over Chester, and Matt Dillon gets to watch the total humiliation of Chester. Once again, Chester strikes out in every way possible.