He's 29 and she's 20 (almost 21), which does add to my uncomfortableness.
She acts/seems young for 20. Apparently her BFF is 15 years old. Eeeeeee.
So if he hangs out with his girlfriend and her "BFF," he'll be a near 30 year old man socializing with, what, a sophomore (in HIGH SCHOOL!!!!) girl? What? No. No no no no no no no. Unless he wants to get arrested.