Dear Dave: I'm a recent college graduate, and I'm determined to follow your plan and get out of debt. My biggest problem is when it comes to dating. Things aren't cheap today, so aside from not dating, how do you handle this area of your life when you're trying to get your finances in order?
First of all, you definitely need to date people. I couldn't have gone without dating, especially at your age. So, I'm not going to tell you to do something I couldn't do.
There's absolutely nothing wrong with dating inexpensively if you're thoughtful. Just don't be so cheap that you're freakish about things. There are plenty of nice, stylish places that don't cost an arm and a leg. A picnic and a Frisbee will go a long way on a pretty day! Your efforts to be a gentleman and make things happen in creative ways will be a lot more charming to any lady worth dating than throwing down an extra $100 at a snooty restaurant you can't afford.
The other thing is to make dating part of your monthly budget. In your situation, it's a legitimate expense, and you need to make it part of your financial game plan. Then, if you're seeing someone on a regular basis, and the money in the "dating" envelope is getting low, you can explain to her that you're working hard to manage your money properly so you'll be wealthy one day.
This will make you even more attractive to the right kind of person, because it shows that you're mature enough and responsible enough to be thinking toward and planning for the future!