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