As I contemplate getting out into the dating world, I would NEVER EVER date a woman who hasn't spent enough time being separated/divorced and figured herself out
You will run into people that are on your same timeline. Fresh off of a D, putting themselves out there for the first time. They are just as nervous as you are. IMO the ladies can tell who is a seasoned dating vet vs someone that is new at the game. The girl I am going out with tonight is on the same timeline I am so I have a certain comfort level with her. I feel like I can be a little more open than what I would with someone who has been D'd for 5 years.
Either way I would recommend taking any dates as long as you feel some level of attraction. If nothing else it is good practice for when you find that lady that just sets the moon.