Next Monday you'll feel more confident. After the gym you'll feel more confident. After one more drink you'll feel more confident. After you get a better haircut, a better jacket, a better job.
You've been "getting ready" for two years.
She's standing ten feet away right now. She'll be gone in four minutes. No amount of preparation will manufacture the courage that only comes from moving your feet.
Walk over. Stumble through the first sentence. Let it be clumsy. Let it be imperfect. You will feel more alive in those ten seconds than you have all month.
That sentence contains at least five follow-up questions she WANTS you to ask. Where in Florida? What brought you here? How long have you been in the area? What do you miss? How does it compare to here?
She handed them to you on a silver platter. And you said, "Oh cool. I come here every week. I love this band. Ummm... pretty crowded tonight."
She smiled politely. Nodded. And never texted you back.
I was that guy for years. Talking too much. Listening too little. Panicking about my next sentence while she was literally feeding me the answers.
Then I found 22 rules that fixed the whole thing. Rule number one: shut up and listen. She'll tell you exactly what to say.