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