adventures in dating (or always wear your long pants on a first date)

I have a confession to make.  I went on a date with a twenty-five year old.  (This is only news because I’m forty-six.)

young boy in short pants picking dandelion

I know.  I know.  You’re thinking I have a very specific rule about internet dating and twenty-five year olds.  I told Little Boy people would think he was out with his mama.  He gallantly declared he didn’t care what people thought.

Then he proceeded to do a better job of wooing me than any of the men in my age bracket.  Texts to start the day.  Good morning, cutie.  Texts to end the day.  Good night, beautiful.  Phone calls in between.

I have to admit I was intrigued by this man-child and eventually agreed to a Thursday night date.

He suggested going to Jacksonville (about two hours away).  I suggested hanging out at the Farmer’s Market here in town. He countered with the drive-in one town over.

What the heck, I thought.  Haven’t been to the drive-in since Sweetness and The Genius were little.  And this is my Year of Yes.

Come the night of the big date, I was dressed in a cute little sundress.  He was in shorts, an undershirt and an untucked, unbuttoned, short-sleeved Oxford shirt.

Little Boy was just late enough that we had to have dinner at Sonic.  Waitresses in roller skates.  Parking under an oak tree eating chili cheese dogs.

Somehow the movie seemed appropriate for a drive-in date with a man-child.  The Three Stooges.  Little Boy didn’t seem to realize it was a remake.

Despite his proclamations that he loves dating older women because we have more to talk about, we really didn’t.  Until we were on our way home and I mentioned Sweetness.

Now we have an all-new definition of awkward – the moment your twenty-five year old date realizes he knows your nineteen-year-old daughter.  Knows as in having mutual friends and hanging out with the same crowd.

It was at that point that I actually started enjoying the date.  I laughingly told him I couldn’t wait to tell her.  He pleaded with me not to.  Aha!  So much for the “I don’t care what people think” proclamation.

Of course, as soon as I got back to my car, I did call Sweetness.

“Hey, baby girl, remember the twenty-five year old who was taking me to the drive-in? You know him!”

“Mama, you’re so ridiculous I can’t even talk to you right now.”  

That seemed fair enough, and made me laugh again.  After exchanging I love you’s, we hung up.  As long as she still loves me, all is right in my world.

You would think that would be enough to discourage a man-child, but no.  Little Boy continued texting for days, even though I quit responding.

Then came the email.  “Hey, I gotta ask you, why you gonna leave me hanging like that.”

I do obtuse well.  It’s my special gift.  “What do you mean?”

After a flurry of simultaneous emails and texts, I broke it down for him.

If you are in my daughter’s peer group, I am not dating you.


If you don’t want my daughter to know I’m dating you, I am not dating you.


You may have a lot to talk about to me, but I do not have a lot to talk about with you.


And since you’ve pushed me instead of graciously accepting my non-response as it was intended, one last piece of advice.  A drive-in is not a great FIRST date if you want to date grown-ups.  It might be a fun date ten or fifteen, but not Date One. 


A drive-in one city away added to you not wanting Sweetness to know confirms you DO care what people think about our age differences. 


My shot at impersonating Demi Moore didn’t work out for me.  But on the the plus side, I have something else to write about in my blog.  So I don’t count it all a loss.  And honestly, I do love a chili cheese dog.

Question:  Who is the most inappropriate person you ever dated?  And how did it turn out?

6 thoughts on “adventures in dating (or always wear your long pants on a first date)

  1. When I was in my late 30s I got a call at work one time from a young admirer (in his early 20s). He gave the receptionist a fictitious name when she asked him who she could tell me was calling. The first thing he said when I picked up my line was “don’t tell my mom I am calling you.” My response was, if you have to start the conversation like that you should not be calling me!

  2. Pingback: are you tired of starting over yet? | my balanced life

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