Watch on Soap2day. A young man's quest to lose his virginity spirals into a hilarious journey of self-discovery. Meet Jeffery—awkward, endearing, and desperate to shed his V-card. After his fake sex stories backfire at work, his friends set him up on a series of cringeworthy dates, including a mix-up with a gay man that leads to unexpected revelations. As Jeffery stumbles through one absurd failure after another, he begins to realize that sex isn’t the answer—self-love and connection are. How to Break Your Virginity is a sharp, heartfelt comedy about identity, friendship, and learning to love yourself, no matter who you are.