Dating Over 40: What if He Sets Dates Up via Text and Email?

Dating Over 40 - Date by Text

Dear Ronnie – The Dating Coach,

Men in Chicago are so frustrating! I met a new guy recently online who looks great “on paper”. We talked on the phone and he said he’d get back in touch to set up a plan to meet me the next day. It would have been so much more easier if he just set up the plan while we were talking. But no. Like most guys in Chicago, he’s too last minute or on the go or whatever.

He sent me a text the next morning saying he’d let me know later when and where we would meet and how he was looking forward to seeing me. Again – he put me off! So I texted back to say he needed to let me know by noon so I could plan accordingly or we’d have to reschedule. My girlfriend said that message was way harsh but I am so sick of this run around.

He emailed me at 5pm with a place to meet. I didn’t even see the email! When I did, I texted him back to say I was no longer free for the evening. What am I to make of this? These loosey goosey plan making actions are driving me crazy. Suggestions?

Texted Out

Dear TO,

I understand how frustrating this is for you. My dating coaching clients complain about the very same thing. It’s a nuisance, an annoyance and a fact of dating over 40. So what’s a women to do?

Many of my clients have found  it can be so simple to let a man know your preference for communicating date details. Just tell him. Crazy huh? But it’s that simple. Here’s a line to try, “Let’s make plans now while were on the phone so its easy to coordinate.”  Or if the texting and email come before the phone call, say, “I’d love to make plans, give me  call at_____” and supply your number.

Don’t let your frustration about this sloppy or lazy communication style cloud your view of every man. They don’t know your preferences unless you tell them.  Women dating over 40 or dating after divorce think these ideas should be obvious, but unfortunately, they are not universally accepted ways of behaving among all daters if you get my drift.

One more suggestion regarding your friend’s comment. When you explain preferences to men, it works best to find a way to keep it positive and upbeat. You probably want to avoid sounding irritated or providing a deadline. That might come across as demanding because its too business-like.

You may think your request is for simple courtesy, and truth be told it is. But from a man’s perspective, he might think the same way. So you want to share your preferences in a soft and inviting way. You are asking a man to conform to your way of doing things, so think first and ask sweetly. That’s one of the best pieces of advice any dating coaching client can put into practice.

You know the old saying, “You attract more bees with honey”?  That saying has been around forever because it works. It offers very sound wisdom.

A man who is truly interested will want to please you because he wants to win you over. Give him a chance to show you that side of him.

photo credit Christopher Chan

Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony,,, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

1 thought on “Dating Over 40: What if He Sets Dates Up via Text and Email?”

  1. I can totally relate to this. A few years ago I decided to do something about being single and within weeks I had a few dates lined up.

    One guy was a work colleague from another department. He was so caught up in the details of the perfect date and texting so much, that it was became too hard. I ended up so annoyed with all the texting and details, that when we did finally catch up I was so not into being there.

    But then again it was a very quick learning curve – he was a Perfect Melancholy (perfectionist) while I am a mix between Popular Sanguine and Powerful Choleric – more spontanious.

    Personalities really do come into play with dating… perhaps texting just shows it up more!


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