Dating after a long break is tough under any circumstance. Whether you've just gotten out of a long term relationship with your girlfriend or you've been focusing on other aspects of your life, the rules of dating change as time goes by. As a newly single woman, you're ready to mingle.. but the problem is you don't know how. If you've been out of the dating pool for awhile, it's completely understandable that you find it scary to step back in. However, you shouldn't let that stop you from finding love and having the time of your life.