Not attached to any ends. Just an achievement.
After 50 Filly requests, there is an event with Tiffani about quitting.
After 75 Filly requests, there's another event with Tiffani. You must have no requests waiting to trigger this. They go out to drink at Iksel's ''exactly two days later''. And that's when you need to show up for the ''Legendary Drunkard'' trophy.
There's an event afterward with Filly.