I don't know exactly what she's thinking here, but the moment I first saw this shot of Jill, I had a very specific (and regional) interpretation of it:
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For context, this occurs when Tybalt is wanting to set up his first date with Jill, and he runs off to check his calendar to schedule it.
To me, she looks like she's thinking, "Bless his heart." For anyone from the South (U.S., that is), you know this is not a compliment. It's probably one of the most polite ways you can call someone a moron. It's like saying, "You're an absolute idiot, but you can't help that you're an absolute idiot because surely you must be brain damaged."
Examples:
"Fuckface didn't know any new car would have air conditioning. Bless his heart."
"Jill started taking off her clothes in Fuckface's bedroom, but he didn't know what was happening. Bless his heart."
"Dawe showed up for class in the wrong classroom. Bless his heart."
"Arieth can't tell dog food from soup. Bless her heart."
"J.A.L. can't keep a new F95 handle for more than an hour or two. Bless his heart."
So, when Tybalt says this:
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I imagine Jill thinking this:
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