Dating By The Time You’re 40+ Part 2

Five things to consider before you date again (continued)

Mar 10, 2011 by

Let’s be real. Dating at 40+ is different, and the same time, it’s pretty much as it was when we were in our 20’s. The difference now is that we (and he)  just might have a better idea of what we want .. or not. If you missed Part 1 (#1 It’s not all their fault and #2 Get happy with your life and with yourself) check it out and come back.


Stop thinking about what it’s going to be like when you meet his bratty seven-year-old.   Don’t think long-term or long haul—because if you haven’t got to the first drink, you certainly aren’t going to meet the kid.  Take a step back from all those anxiety-causing thoughts of how miserable you might be together and think about this:  what kinds of guy do you *really* honestly and truthfully want anyway?  Maybe, deep down, you don’t want Mr. Right-for-Marriage.  Maybe you just want Mr. Right Now, who’s cute and a good lay.

Oh, don’t be so shocked—be so honest!  Get brutally, down-to-earthy honest with yourself and what you want.  What you might find out about your wants and desires could shock you.  Keep in mind, too, that whatever you want now isn’t necessarily written in stone.  You can change what you want when you’ve figured out why you want it and what you might have to do to get it.

Getting radically honest with myself about what I want surprised me, but has made me all the happier.  For years I thought I wanted that wonderful relationship with Mr. Successful Guy, and we would be going here and there to all sorts of local business events and fundraisers and have our picture in the paper on the society page.   Man! Was I wrong!  After being divorced for 10 years, I realized that I really like my own space that I’m very independent, and that someone who’s independent like me, who likes to drift along in the experience of life, is a far better fit than someone who wants to “build a life together.”


Remember when you were younger, and you went out with a group of your girlfriends and met up with a bunch of guys who were grabbing a few beers after the company softball game?

Yeah, that’s what young people do.  Middle-aged people don’t do that.  When we go out with our girlfriends, we’re not necessarily looking to meet up with a bunch of guys.

And men, well, most middle aged men don’t go out in groups of other middle-aged men (unless at a conference or something.)  There are lots of reasons for this:  maybe they work long hours and are perfectly happy going home and spending a bit of time in front of the TV or computer. Maybe they prefer now to go golfing rather than hanging out in hip bars cruising for chicks.

And, believe it or not, when middle-aged men are out with their friends, there’s a chance that they’re not looking for women.  They could just be out to enjoy a few rounds of golf or fishing, or doing that volunteer stint with Habitat for Humanity without thinking about scoring.  Men mellow out a bit in middle-age and start to enjoy different kinds of friendships, like being mentors or instructors.  Conscious skirt-chasing—the kind that roving packs of 20 year olds do on Friday and Saturday night—just isn’t there anymore.

Maybe because some of these men are looking for someone serious too.

Think about that one.

So if you’re thinking you might just flirtatiously bump into Mr. Right while swilling a martini or swinging a hammer, reconsider this tactic.  It may actually be the worst and most desperate, man-meeting strategy out there for someone over 40.


If your job doesn’t require that you keep up on the changes in fashion and makeup, you might have to make some changes.  Both men and women are attracted to people whose style are up to date and put together, not in another time period or ill-fitting size demographic.

In other words:  Style Denial is a total killer.

Women project Style Denial through both clothes and makeup.  So, if you started tweezing your eyebrows in high school, and that was sometime in the 70’s or 80’s, you might want to think about having a professional show you what looks good now for your face.  If you’ve always dyed your own hair its own particular shade of purple-red or antique blonde, you might want to consider having a professional make it a bit more natural.  You might want to get rid of those stretchy pants, that fashion-victim Ed Hardy ensemble (yes, you *can* overdo a trend), or anything that smacks of another decade or a size you haven’t seen in years.  It might have been great back in the day, but those days are over, baby.

On the other hand, if you’ve deteriorated into frump-tastic grandma-wear track suits, and never wear makeup unless compelled to, then perhaps you’re in need of more help than your age-denial inflicted counterparts.

Yes, I know this is a lot to take in, and it’s taken me about 10 years of dating to figure a lot of this out.  Not to mention that there are a whole lot of details to each of these items that need elaboration.  But I’d bet that you’ve never even considered some of these things.  Think about it.  There will be more later….

Dating By The Time You’re 40+ Part 1

Graphic credit: Disability Scoop

About the Author

Tish Grier Has Written 6 Articles For Us!

I am a freelance writer with a focus on the impact of social media on the newspaper industry for I also am a social media strategist. I have been a professional blogger for a multi-national telecom, a thought-leader blog network and several noteworthy projects, as well as a community developer for, Assignment Zero, and NewsTrust.
Getting The Latest Tweet...
Did you know Tish has a blog? Go see what you're missing...
Share With Your Girlfriends and Enjoy:
  • Facebook
  • Twitter
  • email
  • Print
  • Digg
  • StumbleUpon
  • Google Bookmarks
  • FriendFeed
  • LinkedIn
  • Posterous
  • Tumblr

Related Posts

Share This


  1. Tish,

    Loved your two posts. Item #5 is the one I tackled just before Christmas. After taking a year to lose close to 40 lbs – the natural way…watching portions and exercise, but never, never giving up my red wine – it was time for a new wardrobe. Since I’m not a big shopper and had no clue what even looked great on me these days, I hired an image consultant. She shopped for me and had everything ready for me when I got to the store. In 2 hours, I had a new wardrobe, which includes shoes and jewelry. Best decision I’ve made in years. Now, I don’t stress over what to wear. I know whatever I pull out of the closet is going to look great. And by the way, the very day of the shopping expedition, I also “donated” every single outdated item so that there was no chance I’d ever wear them again:)

  2. Rebecca Crichton

    Tish, I really appreciate the honesty in this. Being willing to redo the narrative that has driven us about who we need to be with and how we attract those people is hard but critical. And knowing what stage in life we are at and what fits that stage internally and externally is especially important. Thanks for the reality check.


  1. Dating By The Time You’re 40+ Part 1 | All The Single Girlfriends - [...] Part 2 About the AuthorTish Grier Has Written 3 Articles For Us!I am a freelance writer with a focus…

Leave a Reply

Your email address will not be published. Required fields are marked *