Why You Should Date Someone Older And Someone Wayyy Younger

by Jessica Ashley
Originally Published: 
An older man dressed up for a date wearing a tie and holding a bouquet of flowers

I was ready to date about four minutes after I left my husband.

Some women need to take a breather before they hurl themselves into this new life, but my body and my brain were screaming for attention. Unfortunately, no eligible men were magically appearing in my dining room or even on the playground. And since the only other place I spent my hours as a newly single mom was my laptop, it was clear that I’d have to join every guy I’d gone to high school with on an online dating site.

Every guy I went to high school with was online dating? Oh, yes. I know because I saw them there, listed among the pictures of thousands of men sitting on cheap leather couches and standing with strippers and having the best time ever on a boat with two or three other women cropped/blurred/pixelated out of the picture.

This discovery eliminated a wide swath of men in my age bracket, who were all very busy doing…other things. Like strippers. And boating.

When I input preferences such as “no smoking” and “has possibly been or perhaps will be or is thinking about being employed,” the field narrowed even further. Clearly it was time for me to step outside my comfort zone. (Since my comfort zone for the previous year or so had been a husband who didn’t acknowledge me most days, that left me a lot of flexibility.)

I had two options: older men and younger men. I set my sights on men who were older but still a ways off from my own dad’s age bracket, and opened myself to the possibility of men who still needed permission from a parent to rent a car.

Here’s what I learned from dating at two ends of the eligible man spectrum.

Be warned: There are generalizations here. Not every man fits perfectly into a younger/older category, just like not every hipster has an unkempt beard and oversized ’80s plastic glasses. Oh, who are we kidding? Take this for what it is worth.

Older men may have a ticking biological/marriage clock. Guys over 40 were the only men I dated who gasped, did a spit-take, argued or looked irritated when I said I had no plans to get married ever, ever again during my time on this planet. Those who did want to make it legal or have more children seemed to be playing a game of beat the stopwatch and were confounded to meet a woman who wasn’t running that race. Younger guys, on the other hand? They have all the time in the damn world and can’t even think about some lady’s aging ovaries if she’s showing some cleav.

Younger men have dated models. All of them. All of the younger men have dated all of the models. They also really need to impress upon you repeatedly that they have, in fact, dated a model. Or four. Models? Dated them. All. An older date, on the other hand, would really prefer that you do not ask him whom he has dated or what his partner number is because that is so the-era-in-which-he-dated-models.

Older men understand divorce. Most of the men who were 40+ had a divorce (or two) in their history, and all of them identified with how brutal break-ups are. They got where I was in the process of ending a marriage and didn’t pressure me to give too much of myself—or pretend that court and custody issues and that part of my life weren’t excruciating. They often offered solid advice and a macro perspective that helped soothe my stress.

Younger men distract you from divorce. Why, yes, ogling my bewbs and complimenting my ass will take my mind off family court. So will youthful, dewy skin, abs that come from many, many available hours to spend in the gym, and the gorgeous suits that disposable income can buy. Unfortunately, the agony of hearing the drawn-out details of a relationship with a “psychotic” college sweetheart or a persuasive argument about why I should return to this guy’s parents’ house for a romp is not exactly the distraction a divorcée needs.

Older men have resources. You decide: A car with at least one seat cleaned off enough for you to sit on it (older man) or a bus pass with at least $100 on it (younger man). A Costco carton of condoms (older) or one, maybe two, with questionable use-by dates (younger). A healthy 401(k) (older) and a nice bottle of red already breathing on the counter (older), or Spam and Ramen in the pantry (younger) and a death-glare roommate who is in love with your date (younger). A totally freed-up weekend schedule (also younger), emergency tampons from the last lady he dated (older), a comforter that his mom and dad got for their wedding (younger), enough wiggle room on the credit card to take off for a spontaneous weekend (older), a job he won’t blow off after a raucous night (older), 8,000 Facebook friends (younger).

Younger men have energy. Men over 40 really prefer to be at home and heading to bed at 9. Do not call, text or Skype these guys—even with deliciously raunchy invitations—after the news. They won’t get the message until the next morning, when the magic and wine have dulled to embarrassing hues. Young men, on the other hand, don’t get off work until 3 a.m., and their libidos are set to an alarm of sunrise. Expect all kinds of ramped-up attention in the wee hours.

Older men are more likely to be fathers. Older and single on the dating sites often equates with kids from another relationship. While this can be hard on scheduling—dueling visitation weekends fill up the calendar fast—the benefit of dating another parent is that they will probably understand when a little one is sick and you have to cancel last minute, or that you can’t talk on the phone during witching hour and that you may have rules about sleepovers, introductions and other dating single-parent stuff.

Younger men are more likely to live with their mothers. Once a young man pinged me while I was updating my dating profile. He started off with compliments and quickly lapsed into “What RU wearin 2nite” kind of romance. I asked if he was typing to me from his room in his mom’s basement, and he responded, “Yeah, how did U no?” This clearly wasn’t my first rodeo with the twentysomethings. Being young and underpaid or strapped by student debt isn’t easy, and living with parents is certainly a stand-up option for a lot of us at some point—no shame in that. Unless you are trying to get with a woman 15 years your senior.

Younger men will eat candy for dinner. I once went out with a 25-year-old who had a brilliant idea to get burritos at midnight after we’d been at a bar for several hours. My momishness came out instinctually: “Didn’t you eat dinner?!” He answered as I imagined my young son would: “Oh, yeah. I had candy at like 9.” I passed on the burritos, but it was good to know that if I had a hankering for Red Hots, he might take me out for a meal, too.

Older men will pay for dinner. I never went out with an older man who forgot his wallet, but this happened on several occasions with younger men. Dates cost money. Older guys seemed to get this. This is not a requirement for me, as I am of the ye-who-asks-pays ilk. But as an independent woman, it is nice to have a gentleman manage the monies on a date every once in a while. Being old(er) school can have its down sides, however, and one of them is getting irritated at a woman who puts her credit card down first. One dude actually got angry at me and stomped out of the pub when he realized I’d handled the bill while he was in the restroom.

Older men have experience. They appreciate curves and good kissers. They know strategically throwing a Depeche Mode track into the Down and Dirty 2015 playlist will work. They will not make an “Oomph” noise when they pick you up and throw your willing body against a wall. They recognize the gold-star value of your foreplay skills. They have seen stretch marks. That experience will be delicious and will last 10 to 12 minutes. Followed by loud, unapologetic snoring.

Younger men have endurance. If you are a person who likes it five ways until Sunday, well, damnit, a younger man is more likely to offer you seven to nine. They are excited to be there. And in there. Very excited.

Outside of all these generalities, I got to meet and speak to and get close with some fantastic men whom I never would have met if I’d checked the boxes for my own age range on that dating site. I dated a super-sexy tattoo artist (older), an award-winning entrepreneur and descendant of one of our country’s forefathers (younger), a corporate lawyer who took me on some breathtaking hikes (older), someone who opened my ears and iTunes to music that has moved me to soulful places (younger), a hilarious salesman-turned-kindergarten teacher (older) and a Barack Obama lookalike (younger). I loved meeting them all, and most of the time, was relieved to say farewell.

My age experiment findings revealed that I could happily be involved with the right man, no matter whether he was born the decade before me or the decade behind me. That’s good to know.

The right man, as it turned out, was born in the very same year I was, and I am grateful every day that he gets my pop culture references and thinks pictures of me with my ’90s spiral perm and hair-claw bangs are adorable.

He’s fantastic, and that’s worth all the candy dinners and nights with nine solid hours of sleep in the world. He’s right there in the precious middle, just as far from his mom’s basement as he is from retirement, keeping his model-dating stories (mostly) to himself.

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