I encontured a bug in the new update when we were talking about big brother crap like i couldn't select dean after ty and roswell no matter what i did
Depending on when your save was made, it's not flagging a variable that it should be to enable that choice. Starting a new game will fix it as much of a pain as it is, but why it works this way now was to address a much bigger bug, so there was no real way around it.
I strated the game over then went onto roswells route(i really like him) the same thing happened when asking them how they would confess there love but that time i couldn't pick roswell.