Tynan, you last entry about turning 30 was a classic, and I am here to help you.
Step 1: You are never going to get any chicks living in San Francisco, San Franciso is the gayest city in America. You need to relocate to Palo Alto, and date all the cute Google and Facebook engineers. I am sure alot of those girls have $10M+ in stock options.
Step 2: Your wedding will be great. You can have Mystery as your best man, and for your groomsmen you can have Style, Papa, Tyler Durden, and Ramit Sethi from "I will teach you to be rich".
Step 3: Honeymoon? Japan?
After that you are set. But seriously location is everything. I have an uncle who lives on California Street in San Francisco, and he just got married for the first time at age 63. Bad city for chicks.