She's into him, and he's into her. His type are wounded birds, i.e. girls with problems. He's not going to date the popular girl because she has too many friends and will make too many social demands.
I've been on dates like this before. My last one like this was last June, she gave me the "You remind me of my brother" rejection 45 minutes into the date. Afterward, this scene came to mind, this is what getting friend-zoned looks like. Hard lesson learned and now I'm 6 months into a new relationship with another girl I met back in September. Thank god I cleaned that "Nice Guy" shit up!
I could never understand why Portia didn’t sit with her back to the door in order to avoid seeing Tanya. I just had to say that. Otherwise I find all the different relationships interesting to dissect.