I like to imagine a scenario that likely won't happen, but I would like to see play out at least once...
Cindy goes on the photoshoot trip, has a wild time involving drugs, sex & rock'n'roll. All the while sharing stuff on social media and texting friends (revealing just enough details to keep decent reputation with friends).
Wade confesses that this time apart has made an effect on him and he misses his girlfriend and wants to improve himself and their relationship. Ian is there to console him encouraging them to get back together.
Cindy returns home with doubts wether or not she wants this wild life she thought she craved after going in it so fast and rough.
...in my playthrough here she gets back with Wade and in later conversation Ian asks Cindy "where is my thanks for getting you guys back together and motivating Wade to improve himself for you?" as he continues having Cindy as a nice lay for rest of the game, maybe even up to and during Wade x Cindy wedding.