As Jeff towel dries off in his room, he heads into the adjoining room looking for Annie and sees… all of the things that the hotel staff bestowed upon “Mrs. Winger.” He returns downstairs to find her and confronts her about the hotel room. Poor Annie think she’s ruined everything – she thinks that Jeff will assume that she’s insane for following along with the concierge’s assumptions and constructing a fake life, but she’s not AFRAID to tell him, which is really bold and wonderful. Remember that Annie was there to witness Jeff’s breakdown over marriage. She knows how he feels. She knows he gets scared and weird and probably thinks the same thing about her. But she admits to him, anyway, that she’s daydreamed about marrying him and Troy and… well, okay, mostly just Zac Efron. And Jeff doesn’t get scared or creeped out. He doesn’t belittle her or call her a child. He doesn’t run away. And she continues to freely admit that she was hurt that he ditched her (and you can see him swallow in guilt at that), because in spite of what they are or are not romantically, Annie was stung that Jeff would blow a weekend of friendship off with her… just because he didn’t want to spend time together.
She quips: “I mean, we ARE friends… right? Would it have been that painful to hang out together?”
But then Jeff does something that is evidence of how much he has grown as a person, how mature he is. He doesn’t evade the conversation. He doesn’t DIRECTLY answer her question, though, notice. That would have been EASY. He could have said: “No, Annie, I like hanging out with you. Of course. We’re friends. I’m sorry.” He could have given her a mini-Winger speech about something (anything). Instead, he takes their conversation back a thread prior: he addresses the moment Annie is a bit embarrassed about. Instead of taking about their friendship, HE brings up the romantic element and utters a line that is just perfection:
“Well, I can tell you one thing your fantasy got wrong. If we were married… you wouldn’t find me flirting with another woman in a hotel bar.”
The fact that he says this to Annie – that HE, Jeff Winger, the person who a year ago wouldn’t speak about marriage because he thought it was a lie and is now adding to Annie’s fantasy of THEIR marriage together… it’s startling in the best possible way. It shows that Jeff is growing. It shows he’s matured. And it shows, most of all, that he wants to make sure Annie knows she’s cared about by him, in real-life and in her fantasies. The Jeff Winger she’s married to, there? He’s basically saying is not as good as the Jeff Winger she’d be married to in real life. Because that guy would never flirt with another woman and would only have eyes for HER. And really, TRULY, what he’s also telling her is this: “Would Zac Efron do THAT? The guy you’ve daydreamed the most about having a perfect relationship with… sorry. He won’t do what I would do.”"