Relationship and Dating Advice from The Guy’s Perspective: Dating Older Men

So you want to date an older man? Okay. But first, let’s not confuse this with dating an old man. If you’re into that sort of thing, you’re on your own.

We think the best way to approach this topic is breaking it down by relative age.
If you’re under the legal age—which means you’re in high school— you should not be dating an older guy…period. Most freshman and sophomore boys are harmless enough because they are paralyzed by breasts, walking around like zombies carrying their books in front of their privates hiding what’s obvious to everyone around them. But junior and senior guys are more savvy. Their confidence is attractive to you, but that’s why you need to stay far away. They are like just born nomadic vampires with hypnotic powers they can’t control. You might think you’re mature enough to handle them but you’re not. These guys, no matter how cool they seem, are interested in you for one thing, and we hope you’re at least old enough to guess what that is.

Once you’re in college, the game changes, but that doesn’t mean you’re still better off with someone at least close to your age. Especially be wary of your professor that seems a bit too hip, a bit too accessible, a bit too in touch with young people. His hair isn’t really a bushy mane of black hair, but a mirage of hair dye and developer. And he wears those tinted glasses to cover the dark circles under his eyes, while also allowing him free reign to scan for the most alluring co-ed he can find. And that flashy sports car? It’s nice, but he has little money left over to spend on you. Our suggestion: Best to stick with the geeky science major in the adjacent dorm.

Once you’re out of college and comfortably ensconced in your twenties, dating an older guy might not be a bad thing. Guys take a while to mature, and they lag considerably behind women in emotional maturity by five, maybe ten years. So feel free to trade up. But be careful once again. If he’s more than ten years older than you, he’s likely not looking for “The One.” More like Some One. Or anyone.

Once you’re in your thirties and beyond, it’s all good. Older guys will likely appreciate you for some of your more refined qualities. Your ability to have an intelligent conversation will be just as sexy as a low cut blouse, and it will be refreshing to you to actually have someone look you in the eyes while you’re talking.

If you’ve recently retired and are in your golden years, ignore what we said earlier. It’s likely there won’t be very many older guys around, since most of them will have met their great maker, now sitting around a heavenly poker table playing cards for eternity. In that case an old guy will do just fine. However, you might be surprised if you realign your thinking. You might want to consider a younger man, since he’ll be attracted to your sophistication, and knowledge of the finer things in life. And of course it’s easier than you might think, because afterwards he’ll then be able to brag to his friends about the experience, which is half the reason guys do half of the things they do.

Until next time. This is The Guy’s Perspective.