Well dude clearly has a thing for Jill, and I don't think any of us would really blame him - he blew it with her, but it might just be tough to see some girl you always liked end up with some new hotshot freshman who just came in and rescued your entire frat. That can easily lead to the literal definition of envy...and some people handle that differently than others. My hope is he'd be mature about it and just own his mistakes, but this is a DPC game...he might not.
Ya I absolutely expect some friction with Tommy once my MC has Josy stay over some night, lol. I look forward to it too.