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