Dating Advice for The Definitely Not Dead

Gentle readers, we are about to embark on a wonderful journey of dating and education, like a date-ucation.

I have accumulated a large number of questions from inquiring minds that want to know, so what you are about to read is dating advice for those 40-ish and 50-ish.  Maybe older, IDK.  But I know that people in this age range are DEFINITELY not dead and are actively dating.  Some just a little more cluelessly than others.

So, without any further ado.... and I look forward to reading your comments.

Q:  How do you know it's a date, and not just two people doing the same thing together as friends?
A:  In today's world, there is a lot that a person has experienced by the time he or she has hit their 40's and older.  Part of that experience is undoubtedly rejection, and that can even range from not getting as many likes as you would like to a brutal rebuff of unrequited love that is announced in a painfully public place.
So it shouldn't come as a huge surprise, Alex Trebek, that the answer to the $800 question, "Rejection"  is "What do I run away from screaming?"
I think that men and women are afraid to commit to actually wanting to go out with someone to see what they're like, because WHAT IF it doesn't go well or the other person doesn't respond like you hope they will?  That would be rejection and that feels stinky.
So I think the best solution to this problem is this:  Ask.  I wish I had followed my own advice!  I once said to a friend who I hoped who would be more, "Hey, let's eat food together."  We got there, he paid, but then I really felt it going to the friend zone so I turned the conversation to an area of ministry we were both working on.  If I had started this whole thing by saying, "Hey, you are a person I'd like to get to know better.  Would you like to get dinner?"  That would have given this other person a chance to say yes or no with more information upon which to base his answer and he wouldn't have gotten shang-hai'ed over Chinese food.
So, I put this to both men and women:  If you want to get to know someone better, tell them.  Feeling wimpy?  Ask in a text.  But here's the flip side:  No judgment.  If you don't want to get to know this other person better, say so, and don't run to your friends or instantly text, "OH MY WORD.  YOU WILL NEVER BELIEVE WHO JUST ASKED ME TO DINNER."  Appreciate the guts it takes to even dare to think that you could meet someone amazing, and respect it enough to not gossip about it.

Part 2, Kind of
Q:  I just had dinner with this person that I would like to see again.  What is the next step?  How long do I wait to contact him/her?
A:  This is the most critical part of dating.  And so many people, especially women, SCREW THIS UP ROYALLY.
First of all, people of the 1970's and 80's, what was true a long time ago is still true today.
Women, you have got to let the guy initiate the contact after this first get together.  Let his Alpha Male Wolf Pursuer  pursue you!  It is hard-wired into men to pursue.  I can't tell you how many dating stories gone wrong I have heard that started with, "Well, it had been a few days so I called him/texted him/messaged him and I never heard from him again!'  Hands off, ladies!
I would highly recommend having a friend who appreciates your level of crazy on this topic and will let you send her texts that you are dying to send to him!  So you get your text out and yet you are not SCREWING UP your status of being pursued.
Men!  Assuming that you want to see this woman again, do not feel like you need to follow some man handbook that reads, "Date 1:  Wait three days and then call.  For 5 minutes."  Contact her within 24 hours if you want to see her again at any point in time.  It does NOT have to be an expression of undying love or an Oprah interview about how she feels about you.  How about a "hi, had a great time, would like to see you again.  How's your (day within a week) look?"  Trust me, a woman who is worthy of your time and respect will appreciate this.  And if she doesn't, you have saved yourself a ride to CrazyTown on the Struggle Bus.  Haven't you taken enough of those already?
But it bears saying again:  women, do not pursue men.  It's kind of like that book, which I think has some truth to it:  If he is not calling, he is just not that into  you.  And do YOU want to DRIVE the Struggle Bus to Crazy Town?  I think not.  Respect yourself by letting yourself be pursued by a man you like.

Like this?  Have questions of your own?  Email them to  I'll try my best to answer the ones that seem to address the most common issues we adults face as we bravely navigate the waters of dating.


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