Dear Dr. Date,
A $5 bet on which is better: “getting some” and hoping for a relationship, or no action and gaining a friendship. On Tuesday, you ended the column deciding the roommate getting “a bit of action” would be the winner of the $5 bet.
I beg to differ. The gentleman (yes, I mean gentleman) should most certainly win the bet. I find it to be poor logic to say that it’s better to “get some” over developing a potentially good friendship. Both ways do see results and, while the shallow guy might get temporary, short-lived physical stimulation, the other guy will gain the long-term benefits of having a friend.
I’ve learned from past experiences that relationships starting off with physical intimacy just don’t work out. I was in a relationship earlier this year that sprang from a night of messing around. We started on the wrong track and struggled for months trying to get back on the right track … needless to say, it didn’t work out.
We could have saved a lot of heartache (especially on my behalf) if we were friends first. After all, friendship is a good, solid basis for a relationship. If we took that extra step to get to know each other, we could have discovered one of two things: 1) A relationship can work, or 2) A relationship can’t work. Even if a relationship didn’t work, we would still have the friendship, that, in my eye, is a far better blessing. Lovers might come and go, but true friends will always be there. In answer to the $5 bet, I would say the roommate who has set his moral standards higher should win.
— The Gentleman

Please reread the letter from Tuesday more carefully. The author chooses to fool around first, but has no trouble forming both friendships and relationships with these women. His roommate likes to build a friendship first. The problem is that the author gets both physical intimacy and emotional enrichment, while his roommate gets neither. As long as the story I heard is correct, then, yes, the author wins the bet.
Too many men and women take what they believe to be a very high road when it comes to dating. They try to avoid all the negative stereotypes associated with players and flirts. I think it’s great to rewrite the book on dating and better yet to have each person write their own book. The problem arises when people use this superior dating attitude as camouflage for shyness.
Does it really make you a gentleman if you don’t say what you are thinking because you are too afraid of rejection?
I don’t like bets like this because really there is no winner. It’s all about being happy, my friends. Find your own way to your own happy place and don’t hurt anyone along the way.