This achievement is quite easy to get, the list of activities to complete is not as long as many think it is. If you pause the game, go to the stats menu then to unlocks and then progress, there is a huge list of activities to do. Next to each activity is a YES or NO indicating whether you have completed it or not. The only activities that matter for this achievement are as follows:
Get a Haircut
Get a Tattoo
Buy clothes
Play Golf
Play Tennis
Play Darts
Complete at least one challange in the Shooting Range
Have an Arm Wrestle
Hold up a store
Buy a private dance at the Strip Club
Lastly, make sure you do not quit out of any of the activities before completion as i have read that it doesn't count towards the achievement. You don't have to win at the games as I lost my game of golf.
Hope this guide is helpful, please leave a comment if you have any questions or if you have any troubles. :)