To a certain extend, there is a reason for Ian´s face. Viktoria was more a Mom for him than his real Mother ever was and she is the only woman currently in game he really respects. There are hints that Ian has a rather big, if hidden crush on Edwin´s mom.Another point: When the MC is interrogating Felicia during exhibition week 2 and talks about his mom and how she never re-married and hardly dates, we actually get a shot of Ian making a weird facial expression for no apparent reason...
Personally I can see one of the endings of PC being Ian becoming a History teacher/professor and in a relationship with Vicki.