Going After Pretty Women when You're Not so Pretty Yourself

Should men pursue women that are a whole lot more attractive than they are? The verdict is still out, but consider what happens when you don't.

If you aren't at least attempting to date women that are out of your league it suggests you've digressed. If you do, and you are remotely successful with that woman it bodes good for you once you've gotten that out of your system and you date "closer to your league". What women is truly interested in men that have not at least tried to date up, regardless of how intimidate by that it may make them feel.

Men eventually realize that women that are indeed "out of their league" are not necessarily either what they are truly looking for or what is best for them. If being out of your league suggests the woman is making a lot more money than you are it could simply be a matter of your not either being able to, or willing to, satisfy her materialistic needs, assuming she's that shallow. If it is matter of intelligence, well you can always become smarter yourself and if it is a matter of looks you probably have run into a truly vain, or shallow, individual, which is not to stereotype. There is a perfectly good chance that a woman who is your superior in one or all three of those areas can find something to like and love about you, just that you are talking to the wrong person.

Men are as entitled as women to get that initial shallow boost of self esteem that does come from dating people that you have either convinced yourself is out of your league or that you have allowed the women you have attempted to date to tell you that they are out of your league. Inevitably someone comes along that doesn't do that; whether or not that is the one for you or simply a nice friend is between the two of you, but in any event ...