A coworker joked that if I was in a room full of guys and they all made over $100,000 and only one made $40,000, I’d find the $40,000 man. Such is my plight. Why do I go after the underdog? It’s certainly not intentional. My last date was from match.com and there was no way of knowing what his income was. Sure enough, by my calculations, he’s at $40,000. It’s not that there’s anything wrong with a menial income, but at my age, 50, it impacts so many aspects of a relationship.