SHANE: [on phone] Uh huh . . . All I know is I don’t have it, so it’s gotta be at your place . . . You’re not looking for it, you’re watching TV, I can tell . . . Yeah, whatever. I’ll just get a new one. So, what are we doing tonight? . . . I don’t know, I’m sick of eating. I’ve been eating like a pig, I feel all bloaty . . . It is so a word, it’s a word ’cause I said it. That’s how words get invented, ’cause people say them and then other people say them . . . You’re such a jerk sometimes and I’m always nice to you . . .
We have seen Jess and Shane embrace and kiss on the show, but this is the only time we ever hear them communicate, and it’s just one side of a brief telephone conversation. When a jealous Rory overhears it, she seems to use it as ammunition against Shane, as evidence that Shane is not “smart” enough for Jess (like she is).
This is a clear parallel to how Jess feels about Dean – that he’s not smart enough for Rory (like he is). Jess seems to have deliberately chosen a girlfriend who will make Rory feel the way he’s been feeling all along.
What the viewer can pick up from Shane’s side of the conversation is that Jess is not an attentive boyfriend, and Shane is aware of it. She can tell he’s watching television while pretending to be searching for her lost item (we don’t know what it is, but in a later episode she leaves a bra behind, so that could be it). She is also aware that Jess can be a “jerk” to her sometimes, and perhaps Rory should take this as a red flag, because later he isn’t a very attentive boyfriend to her, either.
Whatever Rory thinks of Shane, we can tell that Shane is smart enough to see through Jess to some extent, and is not deluding herself about the relationship. She can also speak up for herself, and lets Jess know how she feels. These are skills that Rory herself will later be lacking in her own relationship with Jess.