Disclaimer: I don't own 30 Rock.
Despite the fact that Liz has thoroughly drooled on them both, bringing Avery along on the excursion to pick up his errant employee after her root canal doesn't seem strange until he realizes that he can't in good conscience leave Liz alone while she's still under the effects of anesthesia.
Fortunately, Avery—whose interest in him seems to be renewed in light of his genuine concern for Liz—isn't offended when he suggests that she take his town car home because he has to stay and make sure Liz doesn't bash in her own skull on her treadmill (or attempt some sort of intercourse with a tree).
He gets Liz situated in her bed easily enough—despite his jokes to the contrary, she's very light and easy to carry—then, for lack of anything better to do, settles down on her couch to watch Top Chef. About twenty minutes into it he hears a muffled cry from Liz's room. He leaps off the couch and hurries in to find her curled up in a ball on her bed, her face buried in her pillow, shoulders shaking.
"Lemon?" he says tentatively, putting his hand on her shoulder.
She tilts her head enough to squint at him. "I dreamt that Dennis ate all my donuts," she whispers. "And then Drew came back and impregnated me and I had triplets and it was awful."
"Are you okay?" he asks cautiously.
She sniffles and wipes her nose with her sleeve. "No one wanted to take me home on Valentine's Day."
Any other time, he might tease her to get her out of this melodramatic mood, but he has a feeling that would just send her into hysterics in this state. He settles more comfortably on the bed, leaning back against the headrest and drawing her head—and the pillow—to rest on his chest. "I'm here, aren't I?"
"That's because you're the best one," she mumbles into the pillow.
"I am," he agrees.
"No," she says forcefully, as if he's misunderstood. "You're the best one. You're handsomer than Drew, and you're not as offensive as Dennis, and you don't ask too much of me like Floyd. You're the best guy in my life." He waits for a few seconds to see if she's done, watching her head rise and fall with his breathing. Finally, she says, "That's sad, isn't it? I'm spending Valentine's Day with my best guy and he'd rather be with a lady who wants to kill penguins and torture puppies."
"To be fair, she never said anything about killing penguins," Jack points out.
Liz snorts a soggy laugh. "You have weird taste in women, Bon Jovi."
He pauses, frowning at the top of her head in consternation. "Lemon, it's Jack. Bon Jovi's not here."
She squints up at him again, a smile teasing her swollen mouth. "Gotcha."
He laughs and, for reasons unbeknownst to him, runs his hand through her hair.
"Can I let you in on a secret, Lemon?"
"Sure. I probably won't remember any of this tomorrow anyway."
He bends his head down to whisper in her ear. "You're my best one, too."
"Tha's nice," she slurs, slumping against him.
He chuckles and strokes her hair again. "Happy Anna Howard Shaw Day, Lemon," he tells her.
"Happy Valentine's Day, Jack," she says, and begins to snore.