I will write to a woman that is probably "out of my league" on occasion, if there are similar interests, and she sounds fun. And if her age range is at least close to me. And close means maybe no more than a year or two off. I know the chances are that they won't be interested, but you never know.
On the other hand, I can't imagine telling someone that I am writing to how little success I am having. What's that about? Looking for sympathy? I can't figure any way that that is attractive!
