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