Getting Around Town With Jamie Shupak: On Not Giving a Damn About Age

That song R. Kelly wrote for Aaliyah? Totally true. And here's why.

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Complex Original

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I’m 30 years old and my boyfriend is 26. While being four years older doesn’t exactly make me a cougar, age was one of the factors that made me hesitate when deciding to date him seriously.

When I was single I thought I wanted to be with an older man. I preferred them to their younger counterparts, thinking that older meant wiser, more mature, and more stable. An older man would know so much more than me—where to eat, where to travel, where to make his moves—and most importantly, how to treat me.

I equated youth with immaturity. But remember the 42-year-old venture capitalist from my last column, the one who couldn’t text using complete words? Eventually I found that, just like him, people don’t always act their age.

I know many middle-aged people who are emotional teenagers. I also know many intelligent, thoughtful people who aren’t old enough to rent a car.

A lot of people find themselves attracted to someone younger or older, and are reluctant to act on it because of some perceived weirdness or societal taboo. Some even limit their potential partners to a very specific age range because that’s what they think they’ll be attracted to. This kind of restriction—made easier and more prevalent by dating sites that encourage you to check age boxes—is lame.

Dating should be about how you connect with and treat another person.

I dated a guy last year who was almost ten years my senior. Despite watching different TV shows and movies growing up, and correlating historical events with different times in our lives, we got along swimmingly. We had similar senses of humor and shared the same family and religious values, too. But it turned out that age in this case meant something else. He was ready to settle down; I wasn’t, and it ended.

Not every woman or relationship will be the same though. Don’t assume that every 23-year-old girl just wants to take shots and dance on bars, or that every 35-year-old woman is ready to walk down the aisle.

Take your time and get to know the person.

It’s hard when there is added pressure from other people, who may see a 40-year-old having dinner with a 30-year-old and make judgments about who’s with who and for what reasons. Public perception is a strong, real force. But the only people who should get to decide whether you’re enjoying each other are you and your companion. Given the opportunity, friends, family, and complete strangers will judge you for being out with somebody who is too fat, too short, too talkative, too cheap, whatever. It is up to you to be confident in the person you date.

Like height or body type, age is one of those things that a person can’t help, but nevertheless they are qualities used to write people off. If you dismiss a potential partner because of their personality, or because you’re on some kind of wedding/baby/white-picket-fence timetable, fine, fair enough. But if you’re not into someone because of the arbitrary time in which their parents created them, you’re missing out.

If you do decide to date outside your age range, don’t fixate on it. A guy who is self-conscious about dating an older woman and tries to pay for everything in an attempt to prove himself looks desperate. The guy dating a younger woman who starts too many sentences with “Back when I was…” sounds like a dad, and no girl wants that from the guy she might sleep with.

You have to live your life, forgetting about what other people think, including that the woman you’re dating might die ten years before/after you. Age has nothing to do with lifespan anyway, and we could all get hit by a taxi and be done tomorrow.

It’s so rare that people meet and like each other that if you start writing people off on the basis of age alone, you’re going to be forcing a lot of conversation with a lot of boring, age-appropriate losers. Go out with a woman because you’re attracted to her, because your personalities are compatible, and because you want to spend time with her.

I know common ground often comes from being at the same place in your life at the same time, which is why I was concerned—appalled, even—that my boyfriend had never seen movies like Dirty Dancing, Ferris Bueller’s Day Off, and The Bodyguard—movies that I grew up watching.

But admittedly, it’s been fun catching him up on the classics.

There’s more to come, too: His birthday is in three weeks and I’m thinking of getting him Howard the Duck on LaserDisc.

In Two Weeks: Find Yourself, Find a Mate

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