Don’t (Specifically) Date Ugly Women.
A lot of guys do try to date women considered ugly because they assume they’ll be easier to deal with and less entitled. Alexander is right, though. That’s a bad strategy. Don’t do it. Women are individuals, first, of course. You can’t judge how someone will behave and what they’ll be like solely (nor even mostly) based on her appearance.
However, in general, more attractive women will have higher self-esteem. They also tend to have superior social skills and are used to being approached so often handle it better and more playfully 1.
Also, no one wants to feel that you’re dating them or are with them as a favor or that they are your second or third choice. It’s horrible. It only breeds resentment and then, likely, contempt. Avoid, avoid, avoid.
I really dislike the numerical categorization of people by attractiveness, but I guess I’ll do it too as it’s easy at least. I’ve dated women most people would call 10s and I’ve dated 3s. Since in all cases I dated them mostly for their personality and compatibility 2, I think my experiences might not be representative. However, all that said, what he concludes with about self-esteem is correct: no matter if absurdly beautiful or plain, that self-esteem portion is what matters.
Just like choosing a beautiful woman only because she’s beautiful is a bad way to do it, picking an ugly woman just because she’s unattractive is also (unsurprisingly) an atrocious strategy.