Why didn't Drew look at her again?

When I saw this magazine cover, I thought: If Taylor Swift was in her 40s now then she must have written her very first hit song 'Teardrops On My Guitar' when she was in her highschool in the late 70s.

And Drew must be a guy with oil-slick hair wearing leather jacket with skinny jeans who listen to Sex Pistols and go partying every Thursday and Friday and Wednesday and Tuesday and weekends nights. And Taylor here, always walk past him when he's talking to his other greasers friend about bikes and stuff while stuffing kids into their lockers in her high-waisted skinny jeans while talking to her female friend about, I don't know, James Dean or stuff. And now she must be thinking, "Ah, those good ol' days..."

So why Drew? Why don't you look at her?

Is he gay?

Did Taylor Swift lie about her age?