Dating an Older Guy comes with Challenges

You’re looking to expand your horizons and date an older guy. But first, you have to kick those age-gap stereotypes to the curb.

This kind of conversation comes up all the time when I’m chatting with some young 20 or 30 somethings at a local bar or event. They tell me their sick of dating guys their age. That they’re immature and have no idea what they want or what they’re doing with their lives.

And then, when I ask whether they would ever consider dating someone older, I get a response like, “sure I’ve thought of it, but isn’t that weird?” Or, “I just wouldn’t know how to act. And what would my friends think of me?”

Dating an older guy is one of those societal stereotypes that just blows my hair back every time I hear it. I can’t believe how many younger women today have this notion that by dating an older man, they’re perceived as an opportunist at best, or some super-traditional, skirts-below-the-knees prude that needs to be taken care of by a man at worst.

They’re worried that walking out of a movie theater hand-in-hand with some guy 5 or 10+ years her senior is a one-way ticket to contemptville. “She must be dating him for the money,” or “she must not feel very confident in herself.”

I’m not going to say that kind of mindset doesn’t exist anymore. There are plenty of idiots out there that enjoy demeaning women for their choice in men. But you can’t live your life trying to make these people think you’re their kind of “normal.” Dating isn’t about age. It’s about the person you’re dating and how you feel with him around. That’s it.

Julieanne Smolinski writes an amazing sex column for GQ. She wrote an article about dating outside your age range. Her take:

“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.”

Now, it’s completely understandable if your young-guys-only bias is due to family planning, having kids, etc. But if you feel uncomfortable dating an older guy because he actually has his act together—you know, with a real job, with real responsibilities—then you may want to revisit those biases of yours.

Just because someone has had more years than you to organize their life shouldn’t be a reason to outright deny them a date. But by all means, date that cute 23-year-old dude working at the Sonic drive-thru who’s halfway done with his Associates at the local community college. He’s, like, the most amazing Guitar Hero player you’ve ever met.

As for your friends, well, I can only say that if they’ve drunk the kool-aid that society handed to them, they may not be totally happy for you. But if you’re happy with him, it doesn’t exactly matter, does it? I can only speak for myself, but it isn’t exactly often that you get real chemistry occurring between two people.

Are you going to pass it up because of what you think people are thinking? Or because of your own insecurities? I certainly hope not!

Listen, it’s so easy to hit up a dating website these days and filter by age. Aren’t there better common denominators you can think of besides “we were both born within a year or two of one another?” Try to open up that filter for once and just see who comes up. How many great guys are you missing out on just because of something they literally had no control over?

And the next time you’re hanging out at a bar and some hot older dude asks if he can buy you a drink, you should see where it goes. You may be surprised by the results.

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