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