I don't have to tell you that the only people who get to decide whether you're enjoying each other as people are you and your dinner companion. Given the opportunity, your friends and strangers will judge you for being out with somebody who is too fat, too thin, to short, too Asian, too a stripper, whatever. It is up to you to be mutually happy with the person you date. I learned this from experience, but also from Ludacris.
Like height or body type, age is one of those strange things about a person that we know they can't help, but nevertheless handily use to write them off. If you dismiss people because of their personalities or because you're on some kind of baby-making timetable, fine, fair enough. But if you're not into someone because of the arbitrary time in which their parents created them—well, more tasty imperfect flesh for the rest of us.
Admittedly, I prefer older guys, only because they tend to be fully fused, like a human skull. You know generally what you're going to get from someone by a certain age, because they've fully committed to their personalities. The idea that young people like older people because of the financial security is irritating. One, because people who give a fuck about money are awful, and because I've met plenty of old, old dudes who are still doing the Somerset Maugham-y cheerful hobo routine.
But, hey, that's just me. I like the Civil War, documentaries, and talking about whiskey as though it were a zaftig prostitute, so old guys and I get along. The only problem I've had with dating outside of my age range is when the other person has been too aware of it. Either he was self-conscious about dating a younger lady, or he tried to pay for everything because he thought I expected it. The only reason a guy is obligated to pay for a woman's dinner in this day and age is because it's his turn, it's her birthday, or because he's a maître d' who spilled something on her. Women who feel otherwise are the reason we get paid 89 cents to their dollar.
But I realize that I'm a young(ish) woman, and biology is a factor, sure. We still live in an age where men get to age like credenzas, and women like unrefrigerated dairy. I think we can all agree that this is stupid and move on. Some old people are hot, some young people are not. The crotch wants what it wants. I don't like to think about kids or how old someone will be when I'm 35, because I try not to fixate on a guy's mortality until after he's met my parents. Besides, age has nothing to do with lifespan, and we could all get hit by a bus tomorrow, like those poor boys from O-Town.
Remember that game, "Guess Who" ? That is the opposite of what picking a person should be like. When you completely remove personality and individual experience from the equation and rely exclusively on stuff like "young," "blue eyes," and "no glasses," you end up with Robert, that weirdo in the beret. Forget about other people, money, and the looming specter of death. It's so rare that people meet and like each other. If we start writing people off based on this completely arbitrary Z-factor, we're really going to end up forcing a lot of conversation with a lot of boring, age-appropriate dullards.
I think that if you meet somebody you like and are attracted to, you meet somebody you like and are attracted to. Go out with people because you want to be naked with them and still hang out with them after. Sure, a lot of compatibility is being at the same place in your life and liking the same things. But while it's weird to have to affirm that "Pootie Tang was a movie," it's worth it if the old-ass dude you force to watch it laughs his ass off.