The starting and ending chapters ones are very simple and easy to get, just start them and get any ending. Hat Trick is also just getting any ending in any of the games.
Short and simple!
In chapter 1, talk to your friend as much as you can. Do not have Jenny get arrested or anything that would have her get detained. Also make her NOT ♥♥♥. You should get a pic from her at the end with her flipping you off.
Not The Fun Kind of Handcuffs
Get Jenny arrested in chapter 1. Typically by doing something indecent in the “Wander Around” option. Sometimes will happen if you go to the lingerie shop and masturbate or food court.
Mainly have her “Do something silly” in chapter 2.
Possible outcome from “Do something silly” in chapter 2.
Do Dudes Dream Of Electric Eggplants?
When Jenny does Truth or Dare with you, answer with the bottom most answers.
Get a high score and good ending in chapter 3. Some options are contextual, where she can only do them at certain times, and sometimes will get arrested, which will not get you the achievement. You will receive a bunch of texts from her to meet up, which means you did it correctly.
This one was very tricky, but how I did it was deny every guy in chapter 2 by “I changed my mind.” Then later doing “Take a seat on his ♥♥♥♥.” Then an option of “Let them use your ass” appeared unlike before, which brings up one of the gangbang scenes, this one is specifically with 5+ people.