Here is the full list of all 15 Five Dates achievements. It takes around 4-5 hours to unlock all of the achievements on Windows.
Failed all 3 first dates, no second date
3rd Date with Shaina was a Success
3rd Date with Paige was a Success
3rd Date with Grace was a Success
Interrogate Grace
Defeated Shaina
3rd Date with Maya was a Success
Read a poem
3rd Date with Saffron was a Success
Stay to help Saffron
Rob a bank
Twerk time
Choose to drink
Pick your first date
Complete your profile