There are one set of twins that were born 87 days apart. One baby  was born on June 1, 2012. The next baby was born on August 26,  2012.
Not until you reach retirement age. Typically that's 65, though many pension plans allow you to start collecting early retirement benefits as early as age 55. If you decide to start receiving benefits before you reach full retirement age, the size of your monthly payout will be less than it would have been if you'd waited. Ask the folks who run your plan to create a simple table showing you how your payments will vary depending on when you start.
A recent Urban Institute analysis finds employees hired at age 25 in half of traditional state and local systems must work 20 or more years to start receiving pension payments worth more than their contributions. For others, the wait extends 30 years or even longer.