A Beginner’s Guide for the Younger Man Wanting to Date an Older Woman
Dos and Don’ts for finding your Mrs. Robinson
Something that happens when you’re dating a man who is a LOT younger than you is that his Millennial friends start looking to you as the Gen-Xer in their lives with all the answers. (Not sure when Gen-Xers have been considered the experts on anything, really, but I’m trying to go with it.) And they especially want a download of all your wisdom around dating and relationships. You’ve been around the proverbial block a few times, so they assume you’ve learned a few things along the way and you might be able to help them figure out how to relate to the beautiful Millennial women in their lives whom they are, for whatever reason, failing to impress.
The problem I’m running into in these situations is that Millennial women are as much a mystery to me as they are to these men who are anxiously hoping that I possess the secret Young-Hot-Woman-Decoder-Ring. I can give them a few basic tips that apply to women in general. (If she invites her girlfriends along on your “date,” she’s probably not that interested in you — that sort of thing.) But really, women in their 20s, as a group, are as inscrutable to me now as they were when I was among them.
After a few of these “what am I doing wrong?” conversations, I’m finding that my answer tends to be: “Trying to date women in their 20s.” Not that I have anything against women in that age range, of course. (I’d date them myself if I were any better at figuring them out.) But my best tip for the younger man who is struggling to understand them is: Try someone older.
We older women aren’t too difficult to understand. We’ve had enough time to figure out what we want and who we like. We’ve had interesting experiences that you might enjoy hearing about and might even want to learn from. And, perhaps best of all, we’re not likely to try to pressure you into marriage any time soon.
However, if you’re a younger man who’s decided he’s going to dip his toe into the older woman dating pool, there are still a few things you need to know. So, although I have almost no advice that will help you with women your own age, I’ve put together the following set of handy Dos and Don’ts to help you get started as you bravely increase the upper age limit on your favorite dating app:
DO get creative with your one-liners. If your best opening salvo is “Hey” or “Ur hot,” you might want to work on that a bit before approaching someone older. Women over 35 have had an awful lot of men say “hey” to them, and over time, a chorus of “hey baby/ur sexy/hi beautiful/[fire emoji]” sort of melds into the background noise of a woman’s life.
Instead, if you can, say something original or funny that acknowledges the differences in your respective experiences. One good line I heard from a younger man, after I told him I had been through a messy divorce, was that he was on the dating app “to lay the groundwork for my own future messy divorce.”
If you can’t muster something like that, at least say something so cheesy that it comes all the way back around to funny. You don’t even have to be original; feel free to use standbys like, “Is there a rainbow today? Because I just found the treasure I’ve been searching for” or “Are you Franklin D. Roosevelt? Because baby, you a dime.” She will laugh at you, but out of amusement, not scorn.
DON’T assume you’re the first younger man to show interest. If you’re in your 20s, and she’s in her 40s or 50s and you found her attractive enough to approach, you can bet she’s got a steady stream of recent PhDs and college athletes wanting to rock her world. Women who set their age preferences widely enough to include men 15-20 years younger than them may get dozens of messages every week from men in that age range. Given these kinds of numbers, if you assume you’re the only younger option she has on the table, you’re going to come across as hopelessly out of touch.
DO deal with the elephant in the room. The age gap exists, so don’t pretend it doesn’t, or that it doesn’t have any significance. Try really, really hard not to say “age is just a number.” If you just can’t stop yourself from blurting that out, at least follow it up with a sincere acknowledgement that yes, you realize that the older woman/younger man dynamic isn’t all that common, but you find it intriguing nonetheless.
DON’T assume that she’s only looking for a physical connection. Of course, women, like men, date for all kinds of reasons, and it may be that she is primarily looking for sex with a man who doesn’t require medicinal assistance. But don’t assume it, all the same. It’s equally likely that she’s interested in the emotional and psychological benefits of dating a man who was raised after the Reagan years. (More on this in the next tip.)
DO ask why she’s interested in younger men. Women who date significantly younger have often given this a lot of thought, and if you’re interested in the topic, you could find yourself starting a thought-provoking conversation about gender norms and generational differences.
For my own part, I’ve enjoyed interacting with men who were raised in an era when emotional maturity was seen as something important for a man to develop and good communication skills were valued. Men raised in the 70s and 80s too often received the message that men are supposed to be strong, silent, and unmoved, in life and in relationships. The younger men I’ve met have been given more leeway to express their feelings and desires, and it shows. And some of the most interesting conversations I’ve had on this topic have been with those younger men.
DON’T ask for her help with an interview or getting a job. More specifically, if you happen to have an interview scheduled at the company where she works, don’t ask her to put in a good word for you with the hiring committee. (Note that if you don’t follow this particular piece of advice, you’re probably not getting the date OR the job.)
DO compliment her looks. She won’t mind if your main attraction to her is her experience, intelligence, or sophistication. But she’ll want to know that you find her physically attractive as well. Especially if you’re the type of man who looks like he has 20-something women crawling all over him, she’ll want to know that, in your eyes, she can still compete.
There’s no need to go overboard, however. You can tell her she has a nice smile or pretty eyes. Be sincere. Only tell her that she looks younger than her age if you truly believe that. Older women have, over time, developed BS-detectors that could rival the technologies used in the most sophisticated missile-guidance systems.
DON’T talk about your mother. She’s acutely aware of the fact that you have a mother who may not be far apart in age from her. She may even have a son who is not so different from you. But reminding her of those dynamics isn’t going to be conducive to getting her to see you as the man who can help her reach whole new romantic and sexual highs.
DO remember that you are both human beings looking for a connection with another person. Most importantly, be your authentic self. Be honest about your needs and wants and how you think you might be good for each other. And be open to possibility, even in the face of all the contrary messages from society, from the media, from your family, from your friends, and even from women your age. As crazy as it sounds, be open to falling in love. It can happen when you least expect it.
