Welcome aboard! We're happy to have you join the community.
In terms of your specific questions:
1. I would recommend Mint to begin your work of calculating monthly expenses. It's free and connects automagically to your credit cards and banks so that all your charges are inputted as soon as you use your credit/debit card. It's categorization algorithm is about 80% accurate in categorizing your grocery bill as food and your car payment as "auto and transport." You can teach it the other 20%. When my husband and I first started, we tracked our spending on Mint relentlessly to get an accurate picture of our monthly expenses, then worked on ways to cut back. It was the first time we had full visibility into where our money was going, exactly. If you don't choose to use Mint (some people are gun-shy about pooling all their financial information on one website), you can do this yourself with a spreadsheet or Quicken, which I believe is software that lives on your computer, not in the cloud. Using Mint has been a game-changer for us---propelling us from no non-401K retirement savings to over $400K in 2 years.
2. Once you have a sense of your exact categories of monthly expenses, the easiest way to calculate the money needed to retire (in my opinion as a fellow liberal arts major) is to multiply your annual spend by 25. Then, if you want to remove some expenses from your annual spend, you can. We decided not to, because we figure we will repurpose things like mass transit to work with extra travel expenses. YMMV.
Good luck!