Dating the Vintage Guy

“You may have actually lived lives of achievement and may have constructed power-broker pseudo-histories; it doesn’t mean that dating a young woman is always smooth- sailing”

By Mayumi Cabral

Do you even wonder why Catherine Zeta Jones is soooo into Michael Douglas? Or Pauline Luna to Vic Sotto?  There’s something undeniably attractive about the distinguished look of a man with silvery locks. Women regarded those salt and pepper waves as a sign of sophistication, maturity and confidence. The best part about dating an older guy is that he never plays video games – which, I found annoying when I’m with younger men. Also, he has the ability to tell a great story – I really love intelligent conversation. The best part is his expertise in making me feel so beautiful. Yes, it’s all about me and what he finds me incredibly attractive.

But not all older men are created equal. Those silver strands that exude confidence is not the sole reason while we are into someone like you.  This article is really geared towards men over age 40, so if you’re much younger than 40 you’re welcome to read since this is something that will be affecting you in a few years . . . and you might encounter a young vixen like me.

You may have actually lived lives of achievement and may have constructed power-broker pseudo-histories; it doesn’t mean that dating a young woman is always smooth- sailing.  There are certain guidelines to be followed on how to have relationship with a younger woman successfully.

Do treat the relationship the same as you would with someone your own age

Women regardless of age want to be treated equal.  So don’t ever act like a granddaddy who always give in to my every requests and tantrums. I like grown-ups and I like to be treated as one. I hated being spoken down to, babied and mollycoddled.  Don’t treat me as fresh meat to pass the time until someone more serious comes along. I may be younger, but my feelings are just as genuine as yours. Furthermore, don’t presume that you have to “take care” of me emotionally. I am a woman, not a child, even if I am at the same age as your daughter’s.

Don’t talk about your past life all the time.

While I love to hear good stories about life, I don’t want to constantly hear you talk about your kids and their long stints in juvenile retreat. But it’s good to discuss once in a while especially when you ask me about my opinions on some important matters in your family. The differences in level of experiences in life don’t mean I wouldn’t relate to your life or your issues; open up and you never know what wisdom I could offer. Youth might imply less experience, but it doesn’t mean a lack of empathy.

Do dress well and appropriate for your age.

Accept the aging process gracefully. I find Brad Pitt so hot when he started sporting his grey beard.  In fact his handsomeness reached a new level of ruggedness. It’s a common mistake for men, when faced with a hint of liver spots and uneven skin tone to resort to sartorial fashion experimentation. Leave the trend-led streetwear to youngsters who need to compensate for a lack of personality or confidence. You’re old enough to know better. Wear something that you can actually carry-off as “suave” without looking like you’re wearing wedding suit to a funeral. Step away from watches that look like a bedazzled dump-truck tyre and those rappers’ bling-blings, please.

Money talks but don’t flash the cash too freely.

While you earn more than I do, it is well mannered for both sides to be aware of the reality of the situation, and remember there’s a difference between generosity and showing off. Of course, I can surely afford to buy you a cup of coffee from Starbucks or a shot of whisky at Buddha Bar. Always bear in mind that you too deserve someone who is more impressed by the size of your heart than your wallet.

Do watch out for those conversation pitfalls, there are certain lingos that you should avoid when talking to us:

  • “When I was your age . . . ”
  • “Young people now a days are so  . . .”
  • “Oh you weren’t even BORN when this album was released . . .”
  • “You were still a toddler in 1989? OMG!
  • “During my time . . . “
Do not act like a creepy older man.

If you start talking about how hot my boobs are or tell her how you can’t wait to get me back to your place,  I am going to vanish faster than me saying sayonara. Focus more on being confident and classy. If you think a move might be considered creepy, don’t do it, especially if you’re talking over texts, online, or in a public place, regardless if you have established clear rapport or not. This will completely blow your chances with younger women.


Most importantly, be aware of some culture shock. In many ways, you find us as someone who comes from another planet.  We also find senior men from an entirely different earth. When dating a younger woman it is essential to keep in mind how much the world has changed since you first learned how romance works from the likes of Humphrey Bogart and Gregory Peck. Our expectations are often rooted in a relationship model that, for better or worse, has changed dramatically. But one thing that never changes is the manly manners that were now lacking with the younger ones.


MayumiCabralMAYUMI CABRAL Is a wannabe writer who started dating after college – that’s why she’s making up for those dateless college days. She loves to chronicle her adventures and bloopers behind them.  She loves the sun, the moon and the stars.

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