Dating Over 40: I Met 50 Crummy Guys – Now What?

Dear Ronnie – The Dating Coach

I’m at my wit’s end! 

I’m 44, reasonably attractive, nice and make a good living.I decided over the last five months to go on 50 dates with 50 men (kind of like your 90 Day Challenge).  Most I wasn’t attracted to.  Ones that I was attracted to didn’t like me, were not on board with treating me nicely, or were mentally ill (sigh).  I met men through; I met men through plenty of  I met men through joining clubs.  I flirted.  I am nice to everyone; men and women.  I put the word “out there” that I’m looking.

Now after 50 dates, I had to take my profile off the Internet and throw my hands up and say….

Now what? Do you have any suggestions?
At wit’s end

Dear Wit’s,

I’m sorry to hear that you have been unsuccessful so far with your dating journey. You certainly did a lot of things to meet men and for that I commend you! It’s very hard to know why some people find love  more quickly than others. But, Thomas Edison tried to make a light bulb something like 10,000 times.

Of course, I don’t think you should date 10,00 men! That’s just silly. However, how can you just give up? That won’t help either. The point about Thomas Edison is that he kept going until something worked.

Sometimes, it helps to take a break from your dating efforts. Nothing wrong with that. If you are really frustrated, that’s the best thing you can do. Then when you get started again, you’ll be starting fresh.

One thing I can tell you  is that you can feel free to be discerning. It’s hard to tell from your note, but it almost sounds like you dated ANY 50 men. You should feel free to sort and weed men out. Don’t bother dating men who you aren’t attracted too.  On the other hand, sometimes it’s a good thing to try to stretch yourself and see if attraction builds if you find a nice guy you aren’t sure about. Did you meet nice guys who you passed over because of superficial attraction or deeper issues? 

It’s true, you will meet plenty of men who don’t suit you. That is to be expected with dating. Whether it’s their attitude, the way they treat you or other things that keep them from being a good match – that’s why you need to meet lots of men – something you are certainly good at!

Here’s what I recommend to my dating coaching clients – maybe you have already done this, but if not, please give it a try. Make a list of the qualities you want in a man. Things like:
He’s a good person with similar values.
He’s affectionate.
He’s relationship ready.

Also make a list of the qualities you don’t want to experience again such as:
He’s dishonest.
He’s not social.
He doesn’t live a healthy lifestyle.

Getting clear on what you want and don’t want can be very helpful on the journey to find the right man for you.

Wishing you love,
Ronnie – The Dating Coach

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photo credit: chuck caveman

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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