Here is the full list of all 32 Coming Out on Top achievements. It takes around 12-15 hours to unlock all of the achievements on Windows.
Jump up and down in a broken elevator.
Try an exotic ice cream flavor.
Break the fourth wall.
Cuckold someone for poor culinary skills.
Take a laxative.
Commit the crime of rickrolling.
Get your cavity searched.
Attempt to take down your university's corrupt athletics department.
Enjoy a cupcake.
Sell a personal item that belongs to a famous pop star.
Get Phil's romantic ending.
Go with Ian to South America.
Win a game of trivia.
Wear a top hat.
Drink milk like a boss.
Get Amos's romantic ending.
Taste one of life's finer pleasures.
Uproot a plant for a loved one.
Get Alex's romantic ending.
Get busy on a desk.
Destroy a construction site.
Survive a kidnapping.
Make it through the award winning film, "While I Sleep"
Get Brad's romantic ending.
Romance your pet fish.
Get Jed's sexual ending.
Get Jed's romantic ending.
Get your mugshot taken.
Get Ian's romantic ending.
Graduate with honors.
Use Ian's toy.
Use Ian's lube.