Dating After 40

She Said

I doubt there are many men or women who expect to be single after 40. When you reach 40, you think you’ve finally “grown up.”  So what do you do when you find yourself over 40 and single?

The article, “5 Types of Guys You’re Stuck Dating After 40,”  does a good job of summing up rather nicely my recent dating experience.  When you’re over 40 there are basically five types of guys out there.  It’s your job to find the gem among the lemons:

  1. Mr. Set-In-His Ways. “This is the 40-something guy who is totally adjusted to living alone.”  Sure, you want someone who is independent, financially secure, and can take care of themselves, but watch out for the ones that don’t allow room for another person in their lives besides their male friends who are also usually single. He likes his home exactly the way it is; he’s not open to changing his schedule to accommodate you; and whatever baggage he has is now deeply ingrained.  If he’s never been married, the odds of his getting married at this age are very low.  If it’s been awhile since his divorce, then he may have trust issues.  Keep moving.
  2. Mr. Commitmentphobe. “There is no way that a guy goes decades of dating without finding one woman worth sticking with for a decent length of time unless he just doesn’t want to. You can really only get away with this if you’re George Clooney.” And George readily admits that after his divorce earlier in his life he had intimacy issues which took decades for him to get over.  When you’re over 40, do you want to wait decades?  If he isn’t showing any interest in marriage after 6 months of dating, is still talking about his ex in almost every conversation and/or enjoys his “space” and/or other women, run, not walk, and don’t look back.
  3. The Bitter Angry Dude.  He’s angry about his job, his ex, his life in general . . . everybody else’s life.  It’s hard to tell if he got this way because of past relationships or if he’s always been an arse so no woman in her right mind has tolerated him for very long.  You can’t change him.  Instead, get the heck out of Dodge.
  4. The Flake. “This is the 40-something man-child who still doesn’t know how to make plans in advance and can’t stick to any type of schedule.” If you have kids, do you really want another one?  If you don’t have kids, do you want to start raising one now?  Ladies, “The Flake,” like any man, can’t be “trained,” and you can only put up with unpredictability and irresponsibility for so long.  Leave the man-child to his momma.
  5. The Kid Guy.  Here’s where I deviate from the article I’ve been citing.  There are some women out there who don’t want a guy who is really into his kids.  However, I think it’s a real positive to have a man who’s involved with kids.  It shows he’s stable, dependable and caring and will relate well to your own kids.  Those women who don’t want this man and want to be first in his life, ahead of his kids, have their own issues to resolve.  Now if the kid is 25 or 30, that’s a different story.  Keep in mind, however, at this age your guy is likely to have kids.  However, watch out for the ones that are either very entwined with their ex, either in a very positive or very negative way.  He’s still emotionally tied to her! It’s hard enough having a blended family (different households, different rules, etc.) without having to also deal with baby mama drama.

In sum, with lots of planning, insight, patience, and faith you will find the right guy for you.  Don’t settle.  Know and love yourself, know what you can and cannot tolerate, have faith, and the rest will take care of itself.

He Said

I initially thought how much dating after 40 sucked then I read She Said. Now I don’t think it sucks so much. After all, according to the above rules (and I’m sure The Rules dating book would suggest) I am completely a red flag – radioactive – a complete abomination of the dating world.

Screw that.

Dating is a process of elimination especially when over the age of 40. Thus, if your process takes 1 year and 50 dates or 10 years and 5 dates does it really matter? No, it doesn’t because all of the pressures of dating should not come out in one moment of time, a slice of life in which you should NOT be expecting to meet your King but, instead take the moment for what it is intended to be – a nice time out enjoying life.

But if your focus is to reduce your dating pool down to 1% then good luck with finding that 1%. And if you don’t put yourself out there by dating a number of individuals, how else do you expect to find that 1% standing at your door? Perhaps magically appearing via the King’s court of jesters and escorts? Sure, and I will wait for Cinderella during my next Prince’s Ball I attend.

Dating isn’t easy after 40 yet we all have the need for companionship. We like to engage in great conversation, look at a beautiful face, and enjoy a special moment from time to time. Does it mean we expect to marry every woman we date? No, it doesn’t, but it also doesn’t mean we hope to sleep with every woman we date either. This is where eliminating the pressure of dating comes into play; if you allow yourself to get hung up on the details of Mr. Right, then you may find yourself lonely and single for a long time. And if you are okay with that, so be it – just don’t bitch and moan on chat sites about the number of “bad choices” just because you are not attending to your own issues. We all have them.

If I were to list the red flags and baggage individuals bring to a relationship, I wouldn’t get out at all. I’d stay hidden in the comfort of my living room eating ice cream and donuts. Where would that leave me besides with diabetes and a bad heart?

My approach to life is to enjoy it. My philosophy for dating is no different. Therefore:

  1. Enjoy each date for what it is – a date.
  2. Take a moment to engage in meaningful conversation. Who knows what it might lead to, but you might just enjoy the companionship if you allow yourself.
  3. Don’t get involved in sex or offer sex if you can’t handle future rejection. There is nothing wrong with having sexual relations.  Just be aware that you might find yourself attached with your dating companion’s company.
  4. Don’t rush anything. If you’ve made it to 40 and you are still dating, this is the time to slow down. That biological clock has not only ticked away but it is now broken.
  5. Be open to your mature life’s experiences. If you are closed about your opportunities, then you may really miss out on a good thing. Dating over 40 is not the time to miss out, as you are now entering your mid-life experiences.
  6. If you set high expectations, expect high disappointment – meaning you may find yourself alone.

Being alone isn’t altogether a bad thing. You can always get a dog or a cat or goldfish. But to expect the same rules of dating when you were in your 20s is foolish because life has changed. The baggage we accumulate only increases as we get older. Thus, how can you expect to find someone with none? The main secret to dating over 40 is deciding on what baggage you are willing to deal with – then deal with it.


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