I think the trope works when it feels earned. A character who's a virgin often starts from a place of inexperience that isn't just about sex, but about their whole worldview—maybe they're sheltered, naive, or have built the act up into something impossibly huge in their mind. The transformation I find satisfying is when they move from seeing intimacy as a performance or a transaction to understanding it as a dialogue. It's less about 'losing' something and more about gaining a new language for their own desires. They learn to communicate, to set boundaries, or sometimes to break down their own internal ones.
A great example is the way some dark romance handles this. The character’s 'innocence' gets stripped away by circumstances, forcing a brutal kind of self-knowledge. It’s not a sweet awakening; it’s messy and frightening, and they have to rebuild their identity around this new, raw understanding of power and vulnerability. The virginity becomes a symbolic line, and crossing it changes the entire landscape of how they relate to others and themselves. I’m always more interested in the psychological shift than the physical checklist.