(Based on my own playthrough)

Preston:
When you're playing Monopoly with your boyfriend and he keeps cheating-
*cuts to game*
Oh, gotta go to the board walk!

Sole:
*too busy being with MacCready*

I tried romancing him for the first time and it made the whole "Deal with this settlement" thing more...AAAAAAH-
So I took MacCready with me for the rest of the time and ended up dating him.