Dating Over 40: Is He Interested? Discover How Simple that Answer Is!

Have you ever dated a man and felt confused about his interest in you? Does he like you? Does he want to have a relationship? Have things been fuzzy and unclear about his true intentions? You are not alone, but my friend Mattie cleared that all up as she shared her story with  me. And now I’ll tell you all about what she learned…

I was on vacation this past week and spent time in Provincetown, MA (awesome place!) with college girlfriends. How could the topic of dating not come up with me around?

Mattie is still single at 51. She has lived with three different men in very long-term relationships. Even though they didn’t lead to marriage, she still has a solid relationship history.  So I was surprised to hear her tell me this tale about a man who left her feeling confused and uncertain.

She met Dick through a friend  and they hit it off famously. They were very intellectually compatible and the attraction was undeniable from Mattie’s perspective.  They spent every weekend together for over 3 months, going to dinner, having a pizza, attending parties together. people were talking about them as a  couple.

There was just one problem, they were lovers with out benefits. Rather than friends with benefits, Mattie and Dick were not “doing the deed” and this was driving Mattie out of her mind.  She is a reserved type of woman who doesn’t want to make the first move. But Dick was not going there.

In addition, while they did manage to spend the weekend together (except the overnight part) Dick wouldn’t make any plans in advance. As long as she kept her dance card open, he would eventually call to fill it – but no advance planning as if it were all just a spontaneous occurrence.

While Mattie was enjoying the connection and Dick’s company, she was feeling confused and frustrated to say the least. She asked all of her friends what they could make of this situation. People are creative and came up with many excused:

-Maybe he has ED and is too embarrassed to get medication
-Maybe he’s gay
-Maybe he has another girlfriend somewhere and doesn’t want to cheat on her
-Maybe he was sexually abused as a child and today is dysfunctional

Even the friend who fixed her up (Bethany) didn’t know what to say.  Dick had talked with Bethany about Mattie, saying that he wasn’t’ ready for a full relationship yet.

Everyone has their limits, and even though Mattie felt Dick was the perfect man for her in so many ways, something big was lacking. She decided to bring this up because really what other choice did hse have?

She shored up all of her courage and simply asked him to help her understand and define their relationship. Let’s just bottom line things and say that didn’t go well. But I back her 100% in taking this risk because knowing is better than wasting precious time.

And surprisingly, she hasn’t heard from Dick again. What is Mattie’s take way and learning from this experience?

If you have to wonder about a man’s interest in you, move on! When a man who knows what he wants is interested in you, he will pursue you.” Smart cookie that Mattie.

This was completely true for her other three relationships.  Depending on the couple, somewhere between 6-10 dates, you have an idea of a man’s interest level and how you fit into his life. And there are signs to tell you if trouble is brewing:

Does he try to learn about you and your life?
Do you talk on the phone/text/email regularly?
Do you see him during the week and on the weekend?
Does he make plans or wait till the last minute?
Do you go to his place or just yours?
Do you start to meet his friends and family?
Is he willing to meet your friends and family?
Does he tell you about his life and his day or does he seem mysterious?

These are all clues about your man.

Mattie is 1,000% right and that’s ‘s not a typo. If you have to wonder about a man’s interest level after 8 weeks of dating, he could be any of the following:

  • Not that interested
  • Seeing someone else too
  • Has relationship issues
  • Doesn’t know what he wants
  • Has a casual dating agenda

As your dating coach, I must admit that I couldn’t possibly have said this better. Please learn from my friend  Mattie’s experience. If you feel confused, wonder about your guy, ask everyone for dating advice about a man, these are all signs that something isn’t right. Heed the signs when they show up early because one thing I know for sure:


People are at their best during the beginning of the relationship. So if things are confusing from the start, after you give it a shot,  move on to find a man who is right for you.

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.

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