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