Yes, of course they should! Is a girl likely to accept such a man? No, why should she? There are plenty of tall men to choose from. Is the short man likely to be humiliated in the futile attempt to get a tall woman? Of course! It'll be a horrible experience for him. Should he attempt it anyway, even if the odds are overwhelmingly against him? Of course he should! Let me explain!
Men exist to compete with each other for women. That's the role that nature has given us to play. It's our lot in life to be disappointed, humiliated, frustrated, chased away by other men, and be otherwise miserable in our attempt to get women who are simply not in our league. A man who can make rational calculations about love and then act on them is an alien creature, devoid of human emotion.
I think tragedy is part of life and it's unnatural to go to extremes to try to avoid it. We are made better by the pursuit of the tragic end. The short man will try harder when he goes after the tall woman. He'll learn to dance, he'll try to get a better job, he'll try to cultivate wit and conversation. These will all come in useful later when he's eventually (and inevitably) snubbed by the tall woman and enters the competition for quality short women.
By the way, I'm not short myself but I see the dramas that are being played out on the street and I can't help but form an opinion about them. By trying too hard to avoid humiliation short men deprive themselves of essential, ennobling life experiences.
WHAT DO YOU THINK?