I Think Ruth is a Liar
But for a good reason. The first time she saw Richard after he's out on bail, he hadn't noticed her. Only once do we actually see Richard make eye contact when crossing her path at the store and he doesn't smile at her. He's clearly perturbed and walks out without paying for his drink. He was gesturing to the clerk, not Ruth, that he's taking the soda on credit.
However after her fight with Matt, she says she's been seeing him everywhere in town, and once he smiled at her. This makes no sense.
Richard is truly sorry, and he knows he has to pay for what he did, somehow. I think Ruth is lying about him smiling at her because she knew it would provoke Matt into taking the law into his own hands.
"Any particular reason you boys are... naked?"
-Mr. Crabs