Let’s Talk About Dating {in your 40’s}, Baby

Now that I’m divorced, single and trying to manage this dating in my 40’s thing, I’ve thought a lot about how things have changed since my 20’s, but yet they’ve stayed the same.  Dating, to me, is terrifying because I can be super awkward at first, especially if I’m not drunk.  But, there’s something exciting about the unknown.  I think of dating like trying on a new pair of shoes.  Either they hurt like hell and no matter how cute they are, they aren’t worth the cost; or they fit like a glove and you’ll spend whatever it takes to have them on your feet.

I was never a chronic dater, but I did love flirting with guys and a good make out session is still one of my favorite things.  The problem now is that the opportunities are few and far between and the amount of work that goes into even scheduling a date is like herding cats.

Dating in my 40's
Photo Credit: Canva

I relish the days of club hopping, bar hopping, and kissing a stranger in the dark corner of a room at some random party.  It was so easy then, and yet we complained about how hard it was.  The constant worry about getting married and having kids is no longer an issue.  Now all I want is to get dressed up, go out to dinner and forget I’m a mom for a few hours.  Just kidding {not really.}

When I think of my last relationship before I met my husband, I realize why the ex-husband seemed so appealing, even though he was obviously so wrong.  I lived in LA and dude was a Vicodin addict I met at a party in the Hollywood Hills. A party Andy Dick was at, too.  Lesson – if Andy Dick is in attendance at a party you’re at, FYI it’s not the place to be giving out your real phone number.

We’ll call him JR.  He was cool and he made me laugh, we flirted well together, and in retrospect he was probably high as a kite when I first met him.  The fact that he was a Vicodin addict didn’t come out until much later when he asked me to score some pills for him.

In my 20’s when I met a guy, I either gave my real name and my real phone number, or I gave my fake name, Samantha, and my fake phone number which was two digits off from my real phone number.  It was always a split-second decision and it wasn’t an exact science.  Like, if I gave the fake name and then we hung out and he was cool, I had to explain I gave a fake name.  Usually it was funny haha, but sometimes it was not so funny haha, and who wants to be with that guy anyway?

Now, you don’t have a snowballs chance in hell of giving a fake name.  Dating apps and social media make that a little difficult.  But the dating app is supposed to make it easier to date, right?  Wrong.

There’s something so disconnected about swiping left {no thanks} and right {yes, please} on someone based on a few photographs and a poorly written bio.  Then again, when you see in someone’s bio “Me: blah, blah, blah.  You: No Kids” you know up front what you’re getting and which way you should swipe.

Another difference with modern dating is all the texting.  When I was dating in the 90’s, we had all night phone conversations.  That was one of the reasons JR lasted as long as he did; he gave really good phone.  Although I do like texting as much as the next girl, you’re texting on your phone.  Every once in a while, use your phone for its intended purpose and actually have a conversation.  Then again, that would create a more intimate connection, and who wants that?

While technology has changed the game over the last 20 years, the game really hasn’t changed.  We’re human, and as humans we crave love and acceptance.  So, whether you meet someone in person or on an app, you’ll eventually get to a place where you know if you have a connection.  And in a modern world that tries so hard to keep us disconnected, that’s the real challenge.


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