Him potentially having access to drugs (working in a hospital) and that being the reason HG and he met up is a strong possibility to me. I think it's naive btw to think that nowadays it's not possible to get them in a hospital b/c they're locked up and electronically monitored or whatever.
I was a UVA 18 yr old female student at one point in my life... Putting myself back in those shoes, I cannot imagine why she would have (seemingly) rushed to the Downtown Mall on her own at 1am. No one goes there for partying as an undergrad, and it's always been a little creepy at night. Meeting up for drugs is the only logical explanation to me.
As for the POI himself, wow, I'm really perplexed. He's apparently f/b friends with many people with whom I grew up in Cville. People who are very upstanding, and you can also see "Step Up" as a group he's part of on f/b. Supports sexual assault justice and prevention education. I'm just totally shocked and trying to figure out the discrepancy of both the facts (buying her drink, letting her go off alone according to him, etc), the very hard-to-ignore actual potential actions afterwards and these upstanding data points.