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