Take a gap year in Portland, Oregon. It’s an affordable, laid back city with great food and at this age you’re probably still rocking a hipster beard, so you’ll fit right in.
Get Educated in Boston, a city full of the best and brightest minds.
Head to Las Vegas to do something regrettable that will make a great story later.
Early to Mid 20s
Have fun dating in Los Angeles. There are so many hot women here that the 7s think they’re 4s (basically the opposite of where I live in SF).
Do something meaningful in Washington DC. It’s easier to spend your time at a noble yet low-paying job like a non-profit or government position while you’re young and without dependents, and DC is a great city full of interesting and ambitious people.
Work hard and get rich in San Francisco. Get you some of that tech money bro.
Ready to settle down? Go find your future wife in New York City. Like LA, NYC is full of beautiful women, but unlike LA, these women tend to be interesting, smart, or an artsy fartsy mess in a totally irresistible way.
Early to Mid 30s
Propose to your girlfriend in Charleston, SC. It’s one of the most romantic cities in the U.S. and more original than a Hawaii proposal.
Forget originality and honeymoon in Paris, you won’t regret it.
Raise your family in Austin, Texas. It’s a charming city with affordable housing, top notch public schools, great culture, music, bbq, and NO STATE INCOME TAXES, which means plenty of California transplants.