It wouldn't have been any great loss if you married her. As long as you didnt have any kids with her you would've been fine. Since she was rich you might could've even sued her for alimony after the break up lol.
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.