To shoot your shot

American Slang

Definition

To boldly pursue an opportunity—especially expressing romantic interest—despite the risk of rejection.

Examples

"After weeks of overthinking, I decided to shoot my shot and asked Jamie out for coffee."

"If you really want that internship, shoot your shot and email the director with your pitch."

"He knew the timing wasn’t perfect, but he still shot his shot and told his best friend he had feelings for her."