Well in the light of the recent events and seeing Naina being tortured mentally and emotionally, seeing hpw dark her future would be with mamma's boy Sharad? I think he might approve Sam's relationship with Naina when understands that Naina will only prosper with him.
He does know Sam closely. He wpulf defonitely know that Naia called off the relationship because she did not want to break his trust.
I think he will appfove ot on the condotion that they complete their studies. He has a better understanding than the rest of them.
I grew up in the mid-late 90's, it was definitely more conservative but there were people who were liberal, and thinking does evolve with situations, circumstances and ecperience.