Should You Regularly Ping Text Girls Who've Eluded Your Dates?

If she eludes your dates, it can feel tempting to ping her regularly to make sure she doesn’t forget you. Yet there are better follow-up strategies than this.

A reader writes in:

“Chase,

First off, I really value your dating advice; it’s rooted in logic and psychology and that’s how I operate.  It resonates in a big way with me.

So my scenario/question...

There is this one girl.

I’ve known her for about 2 years, but we never hooked up because one of us has always been in a relationship.  I own an organic juice bar and she actually came into the store the other day.  Attraction was definitely strong and she extended her number to me.

We went on a date a few days later; local, food, drinks and just established rapport and comfort.  Of course my end game was to get intimate with her, but it didn’t happen.  I was sort of bummed.  No good night kiss?  I can’t remember the last time that happened.  After the date we texted and I asked if I could call her and I did.  We basically stayed on the phone for almost 2 hours, sort of continuing the date convo.

I asked her on the phone, “Why no kiss?”.  She mentioned that she is shy, that she is attracted to me, the fact that I was on antibiotics for strep throat (day 6) bothered her a bit.  We also talked about how she is a bit messed up from an ex and that recently, she was actually falling for someone hard and chased him but it didn’t work out because he doesn’t want a girlfriend.

I’ve been trying to set up date 2 but it hasn’t happened yet.  I’m just keeping the texts short, direct, nonchalant, non predictable non needy, etc.

I really think she is just hung up on this guy (the one she was recently intimate with and doesn’t want a girlfriend) and after some time I’ll be able to meet her again and put the moves on her.  I’m confident once we’re intimate she will be chasing me.

However, I am by no means not seeing other girls.  I always keep about 3-4 in the rotation so I’m not lonely on a Thursday, Friday, or Saturday night.

MY QUESTION – Texting is such low effort as is Instagram and DM and things of that nature.  Is it ok to use these methods once in awhile to keep a “girl in the loop”?  I feel that timing is everything sometimes and this may be a method to grab her attention at the most opportune time.  What are your thoughts on this?  I’m not sitting home pining over her.  I just feel like the end goal is so close within reach and don’t want to completely give up.  If this is a viable method for achieving my end goal what would you recommend?  Frequency, context, things of that nature?

Thanks you for you time!”

This is a great question. You get some progress with a girl, it feels like it’s close, but then it doesn’t happen. She doesn’t come out on dates, but she still responds to your messages.

So the question is: do you ping her from time to time to see if she’s available and changed her mind? Or do you not? And if you do, how often?