23Entry by burritomouth
22Entry by YepThar
Cracked pays people to make smart memes. Visit the Photoplasty and Pictofacts Workshop to get in on it.
Relationships are hard, and we all make dumb mistakes along the way. Misery loves company, so we asked our readers to tell us about their most awkward, embarrassing, and generally unfortunate romantic encounters.
The most painfully awkward is below, but first, the runners-up:
Congrats, jimclass. You win money.