How to Say the “Right Things” at the Start of Dating

Untangling Early Communication with Your New Man

This is a Question and Answer exchange with a Dating Coaching Client that offers insights into several situations that often come up when dating. My client’s questions are in pink and my answers follow.

“You mentioned that men need to feel needed.  I am very self sufficient and initially I don’t know how to come across to let them feel needed.?  How do I do that?”

All you have to do is not make a man feel “un-needed” by going on and on about how independent and self sufficient you. Nothing wrong with being either, just don’t rub it in a man’s face being so proud of yourself.


“I went out for a walk with a man from and he told me that his old girl friend was looking for someone who made a lot of money because she felt that he should pay for dinners since they were in a committed  relationship.  I feel that same way as she does.  I want him to pay for dinners when we go out.  I don’t have a problem making him meals at my house, but when we go out for dinner I want my date to pay.  What should I do?”

You have two choices. You can decide he’s probably not the right guy for you since he doesn’t have the same views on handling  money as you do. Or you can talk to him about your philosophy – that even in relationship you want to feel like you are on a date. When he pays, it helps you feel special and cherished. As the woman, let him know you will contribute in other ways to balance things out – like cook for him or whatever else you plan to do.

Tell him you see this as a partnership in which both people will feel appreciated. You can even ask him what helps him feel appreciated. And you could offer to pay once in awhile if that makes him happy.

Then see what he says to you in response – he may decide you aren’t the one for him. He may try things your way. Or he may share his viewpoint – then you can decide your next step.


“I also went out with another Match man twice last week.  He said he had a nice time and wanted to see me this weekend. He mentioned Friday and Saturday, but he said that his job is really busy because he has to work for a hospital.   As of today, I haven’t heard from him so I text him today and said “What’s up? Give me a call. ” I didn’t  know what to do, so I am just waiting, but it doesn’t  look good.”

Next time just go ahead and make plans if you haven’t heard from a man you are dating by Wednesday/Thursday. When and if he does call, you will be busy with your own fun life.

You can say to him, “Oh I already made plans but I’m free on Sunday” – or whatever your next opening is. That way you set up and maintain healthy boundaries and help him understand that he needs to call in advance to give you some notice. Plus, now you have your own plans to enjoy if he never does call which does happen.

Providing him with the positive feedback that you’d like to see him and telling him when you are available, sets the rules for dating you without spelling them out directly. It’s a positive way to make sure he knows you are interested in him as well, even though you have your own full life.

In this day and age of dating, independent women tend to think they can just be direct and honest with a guy. Some women tell me they just want to “lay it all out there”. But as your dating coach, I strongly encourage you NOT TO DO THIS.

Once you are in a relationship – of course you can be more direct and honest. But when you are just starting out, men have fragile egos. This makes the direct approach sometimes unpleasant, harsh, and simply unappealing. For so much of life, “presentation is everything” and in dating that goes double!


Photo Credit: Ells

Single for too long, Ronnie wanted to find love. She put her skills from personal development and her spiritual path to work, dating 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to manifesting and midlife dating, she founded It’s Never Too Late to help smart, successful women find love or live an empowered and magical life. Ronnie Ann Ryan, MBA, CCC, is a Certified Coach who has helped 1,000s of midlife women with her Love & Magical Life Coach services. She’s the host of the Breathe Love & Magic podcast and has been featured on NBC, ABC, & Fox News, NPR, BBC, eHarmony,, and Connecticut Magazine among others. Also, Ronnie is the author of 6 books which are available on Amazon.

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