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I like to think that Rio's decision to let Miles follow Gwen was influenced by her own experience getting together with Jeff when they were young.

I think that Rio's family didn't approve of Jeff at all. He was most likely still "running the streets" with Aaron at that time, and I'll bet he just wasn't "it" in terms of what Rio's parents wanted for her. No one in Rio's family supported her in her choices. They probably outright forbade Rio from being with Jeff, and she probably had to sneak out of the house behind her family's back to even see him.

Thinking of it this way kinda makes me see that scene of Rio letting Miles be with Gwen in a whole new way, because we know that Rio and Jeff are assuming that Miles' regular absence and distancing has been him sneaking around to be with Gwen, and Rio giving him her blessing is her saying "i know you're gonna sneak around behind my back to be with her anyway, so at least let me give you my permission to do so. My family didn't support my choices, so let me at least support yours." She doesn't want to keep him locked away from this girl he wants to be with the same way her parents did to her. She doesn't want to push him to have to lie to her the same way she had to lie to her parents.