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Let’s make online dating really, really hard

photo of heart


I thought about this yesterday after a journalist from a major publication called me---asking why it’s so hard to get a second date.

Today I’m going to be very simple and use common sense.

Who/what makes dating hard?

1.      The Media Yep, stupid, insipid dating advice from people who have no idea.  It’s all over the internet—Do this---No, no, no, don’t do that.  Geez. Back to yesterday, and this is what the journalist asked me:   Why are second dates so hard to get?  How can one go mindfully about this? And, the kicker, please share at least 3-4 steps someone should take after a great first date.

Thank God it was on the phone so he didn’t see my major eye roll that my mom never cured me of.

Here’s what I told him: (without saying this is ridiculous)

Wow, if you need 3-4 steps you are doing something wrong.  Stop complicating dating. It's much harder getting to the first date than the 2nd date. This type of advice is what makes dating nerve-wracking.   Keep it simple.

It goes like this:

1.  You had a fun first date. There was chemistry.

2.  You send a follow-up text expressing gratitude and how much fun you had. 

3.  All you are thinking about at the end of the first date is this:   Did I like him/her?  Do I want to go on a second date?

4.  If you are thinking:  Will I marry him/her? Will this be an amazing LTR?  Well, I know why you are having trouble dating.  The other person can sense desperation a mile away.  

5.  A first date is nothing more than a chance to get to know someone and see if you'd like a 2nd date.  A 2nd date is nothing more than a chance to see if you'd like a 3rd date.  And so on, and so on.   Suddenly you are at the "we are exclusive stage".  Yay, you!

I’m not sure he liked my answer. Oh, well, I’m not politically correct.  I want results for my clients, not some BS answer to the media.

Here was his follow-up question:   Is there anything you shouldn't do after a great first date?

A.  Dream about a wedding.  What your children will look like. When you will introduce him to your family.  Where you will go on your first vacay.   Text all your friends that you met the “one”.    Where on the beach you will build a home together.   (Think this is stupid?  Intelligent people actually do this!)

B.  Pressure.  You should not feel any pressure nor exert any pressure on the other person.

Reality check here though:  you BOTH know if the date went well.  And 80% of the time a 2nd date is talked about at the end of the first date---whether it's a movie, disk golf (hot!), or a hike.   


2.       You Yes, you.   You get in the way of going on good dates.  A. Jon* I had a male client (a nice looking 56-year-old man in Philadelphia who is quite accomplished) who had bad photos.  By bad, I mean selfies.  I told Jon no one will ever read about how wonderful you are as just the initial photo will stop them.  Hey, I know how this works.  I work online with men and women all day looking for high potential dates and the first thing we see is your photo.  Online dating is a visual medium.

After 4 coaching calls and no success, he finally acquiesced.  He had some great photos taken by a pro.  Not fancy. Not edited/photoshopped. Not corporate-y.  Just fun and all shot around Center City in Philly with some unique backgrounds.Call 5 was…. the highlight of my day!  Women were messaging him back.  He had 3 dates booked for the next 6 days.

Jon got out of his own way.


If you are serious about dating, I might be able to help you.  The reality is that I only take a limited number of new clients each month.  You can sign up for a 15-minute call with me.  Please fill out as much information for me as possible so we can have an effective call.  The link is


B.  Carolyn

*Sausalito, CA

Lovely 67-year-old woman.  Insistent men had to pursue her.  When she came to me, she had been online for 4 years---gulp, yep, 4 years.  Just sitting there. Hanging out.  Waiting for a man to come find her.   Messaging men?  Out of the question.

The men who messaged her?  She took a week or two to think about them.  (What’s there to think about---there’s two possibilities---yes or no.  "Maybe" is not an option.)  By the time she was ready to get back to them, do you think they were waiting for her?  Then, she complained no one got back to her.

We had a serious talk on our 2nd coaching call.  I’m direct.  Graciously direct.  I didn’t want to waste my time or hers. 

Here was our solution.  For the next week, I was taking over her online dating account.  She gave me permission to message men on her behalf.   Over the next 4 weeks, she went on 7 dates.  4 she liked and they progressed to more dates.  (The other 3 she did not like and said to me “Andrea, why did you pick them” and I just said, “Hey, Carolyn, I’m batting over 57% good dates with you, and I'm pretty darn happy”).

Finally, Carolyn got out of her way.  


*Both clients names and cities have been changed.  Permission was granted by clients.


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