Skip to main content

How to Approach a Younger Man

Breaking the Ice - the latest "Cougar Talk"

The bottom line is that younger men are often shyer and more intimidated by older women and much less likely to make the first move. This alone makes the start up of a relationship with a younger man more difficult for most women. Women still generally have hang-ups regarding being the initiator for a first date and sometimes even a first conversation. I recently heard from a reader that she had significant eye-contact with a younger man and she felt he had “preened” for her. Nothing happened. She waited to see him again and it wasn’t until much later that she made facebook contact.

The key is immediacy. Most men won’t remember a significant “eye-contact” moment a day later, much less a week or a month later. Everything moves faster in the world today including the dating dynamics. Women can remember that special moment weeks or months later, but men may have missed it completely or forgotten it quickly.

Nowadays you have to take advantage of opportunities at meeting someone as they happen. He could be single today and involved tomorrow, so why wait and risk that opportunity never presenting itself again.

Now many older women have plenty of self confidence, but are just out of practice, or they feel it’s not “proper”, or their ego dictates their inability to cross that line. Each woman must confront those demons and analyze for themselves what their personal reasons are for not acting on an opportunity.

Then again, I am obviously not talking to those “stereotyped” but very real prowling “cougars” who can give “cougarism” a questionable reputation. I’m not discussing women who just want a quick roll in the hay and will approach any young thing that crosses their path. I have heard from plenty of younger men that have been resentful of older women because they felt they had been used, their emotions toyed with and then dumped with no explanation. Younger men can be just as emotionally involved as the woman, if not more so. Many have a fascination with us because they believe they won’t encounter the same mind games, immature thinking, and sexual hang-ups that they are frequently faced with when dating girls their own age. By the way, not ALL older women are emotional stable or incapable of mind games.

The point is, if you find yourself interested in a younger man that crosses your path you usually must make some sort of first move. Just engaging him in a longer conversation works, then let him know that you find him interesting and would like to get to know him better.

On the internet, it is less safe but you have more exposure and more opportunities to meet someone. It is, however, just as much a hit and miss as trying to meet anyone of any age via the internet. You never really know who is on the other end of your virtual world. You can only believe half or less of anything anyone tells you online. If you’re intuition or gut feeling is active and usually accurate then listen to it and add a good dose of common sense on top of that.

In person, I have found that finding you have something in common and inviting that man on an adventurous outing (exposing him to something he either loves or has never experienced) to be the easiest and most effective way to get to know him. If you have access to a boat, you tell him you know he loves fishing, would he like to come along. If he likes golfing, you let him know you got two passes to a great golf course, would he like to come along (add you could use a few tips, if you like). You were given two tickets to go ballooning and no one you know is courageous enough to go with you. However, in a pinch, just asking a man if he has time for a cup of coffee works just as well. Or if you know him a little already, asking him to come over to help with a “manly” chore works wonders for both boosting his ego and giving you time alone.

  • Installing electronics
  • help with a computer
  • fixing a gutter, spotting you while you clear the gutters
  • saw off a limb on a tree
  • help lift or move a couch
  • any other lifting, fixing, moving, installing project

Remember the golden rules of dating in general:

  • Make him feel good about himself
  • Don't ever make yourself seem superior
  • Trust your gut (unless you are usually wrong - then trust a friends' gut)
  • Men usually like skirts and heels - not required, but definitely an advantage

Early on:

  • Be yourself, but don't talk about past relationships
  • Don't tell all your dark secrets or faults
  • Keep eye contact
  • Don't pursue hard if he doesn't give the right signals - you're not desperate
  • Always date in public initially and give a friend all the details
    Get enough information about him to give to a friend to find him (safety tip)

Just remember that regardless of whether it's a younger man or not, be true to yourself and to them. Yes, put your best foot forward, but don't be someone you're not and always make the other person feel as you'd like to feel. Anyone younger has to be helped to feel self confident, that's just natural. Do that, and BE confident, everything else will follow.

Scroll to Continue


privateye2500 from Canada, USA, London on November 14, 2011:

A hahahaaa! :}

triosol on September 30, 2010:

Excellent hubs. Voted up. :)

Bernard Anderson on August 05, 2010:

I meet a lot of cougars at bars and don't mind the woman making the first move. This way I'm more confident, she's more confident and we can pursue the conversation from there.

1st Class Travelr from Jackson, MS on June 09, 2010:

I agree Isabella, great article...I too have had an encounter with a younger guy, but things were all good and worked out for two years. I enjoyed your article.

Ludolph L. Misher III on May 07, 2010:

Isabella,Excellent tips on the approach factor...this could make or break an opportunity for that perspective Cougar. I have found that the approach is most effective AFTER much research is done...then she makes the First Move!...Great!

Al Bell on April 25, 2010:

Hah... Grrrrreat!!! You da wo-man. Where was all this stuff when I was a young guy. You might want to read about my encounter with a "Cougar" on my hub titled "Campground Cougars". Scared me to death.

Aden Ford on February 14, 2010:

Here are 3 cant miss rules for how to approach a guy.

Related Articles