The Trouble With Dating A Younger Man


Thought about dating a younger man?

dating a younger man, dating coach, finding loveThat has it’s pros and cons like everything else. Discover the best way to move forward when dating younger.


“Dear Ronnie The Dating Coach for Women,

I’m 39 and just re-entered the dating world after a 17 yr marriage that ended 2.5yrs ago.

I ended up meeting a 27 yr old man at a singles mixer. I did not know he was that much younger until 1 hour into our conversation – when he told me I was shocked and suggested gently he go talk to the other women in his age group.

He continued to pursue – sweetly but aggressively. As we had had such an engaging conversation and as he was so earnest and yes HOT — I figured seize the day and agreed to a date. I planned it and ensured it lasted less than 2 hours. I had a wonderful time and he did too.

After that we texted , made phone calls, had a few more dates – always I let him be the one to contact me first. After a month we had sex. It was ridiculously spectacular. WOW! Lucky me to get to experience something like that.

We agreed from the outset to take it one day at a time and not immediately looking for LTR, but we were monogamous the whole time. Throughout the 3 months we were together he was attentive, courteous, affectionate and such fun .

We knew it wasn’t going to last forever because he needed to move for his career at some point soon. So we decided to enjoy what we could about each other. Fast forward he got a terrific job offer in another state. We agreed not to pursue a long distance relationship. He did say he wanted to remain friends . There was no ill will and it seemed no regrets.

After that, he didn’t text for 4 days (the longest break since this whole thing started. So I broke my own rule and drafted one final email that put some of my feelings into how I viewed our experience together – all positive. I was not asking for any response nor was I trying to rekindle the relationship- just tidying up loose ends.

Then I said as you have avoided me for 4 days – I will respect that and not contact you again. It has been 1 week since that email. I haven’t heard from him. What exactly did I do wrong? Was he a player? Did he honestly care about me? I wish I knew. How do I avoid this same situation? Swear off younger men? I need your help to understand this.

Woeful in Wisconsin”


Dear Woeful,

First of all, congratulations on having a great time! Good for you for seizing the day.

Now, who says you did anything wrong? In your email you said you didn’t expect a response – but now it seems that you did? You agreed to a relationship with no long-term ties. You knew it wouldn’t last. He said he wants to be friends, but you know – people say stuff they know we want to hear.

This had more meaning than you say

Your reaction tells me this relationship had more meaning than you intended. That is the biggest reason why casual relationships and friends with benefits are such difficult emotional territory. It’s hard not to get attached for the vast majority of women, no matter how much they think they can handle it.

I’ll give you a second perspective. What if he will miss you too, but knows cold turkey is the best way to move on? That’s just as possible as him having no feelings at all for you.

Men are good at enjoying the moment

The trouble with dating younger men is the same as dating older men. Some want a relationship and some don’t. In addition, men tend to be very good at enjoying the moment with the women they date. That’s why so many women have a great first date and swear the guy did too, yet never hear from him again.

Don’t cut off all younger men because of this one situation. While his actions seem a little cold, he didn’t really do anything wrong . He followed through on your agreement as it was stated.

There’s nothing wrong with a little fling

It was good for your spirit, a great ego boost and got your engines revving again. You discovered how desirable you are as a woman. This is all good stuff. He was the ideal transitional guy for you. Loads of fun, positive for your self esteem and low risk. If you look at this situation from this perspective, it will make a lot more sense and ease a lot of  the pain.

Gain strength from what you learned

Don’t let yourself suffer over something you knew had no lasting power and was a wonderful experience until the very end. Dating comes with disappointments and rejection. But that’s not even what happened here. You learned how to be vulnerable again. And now you’ll see that you have strength, resolve and can bounce back. The truth about dating is that it is a journey of self discovery. think about everything you learned!

My dating coach advice

As your dating coach, here’s my advice: Take a little time to heal. Now that you now seem to want more, go for it. Keep your new dating agenda of lasting love in mind when you get back out there to meet men. Be honest with yourself and avoid the “no string thing” again. Let men pursue you just as you did with this fellow. Then see who stays in the running for your love.

Good men are out there who want what you want. When you feel ready, make yourself available and hold your head high. You are one hot 39 year old woman. Be proud and know love will be yours.

Wishing you love,

dating coach, find love, meet men











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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