Friend: "He hasn't made the first move yet, so I'll have to shoot my shot and slide up into them DMs"
You: "Shoot your shot..?"
Friend: "Yeah, you know talk to him first."
You: "Ohhh, Good luck"
To be brave and having the audacity to do something that might be embarrassing. “Shooting your shot” takes motivation; it means that you only have one chance to do something before you loose that chance.
Ex. It could be your crush that broke up with her/his bf/gf and you’ve been waiting to speak to her for ages. (That would be your chance to speak to her/him)