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