Dating Over 40: When He Never Does Anything Right

Pointing the Finger at Him
Pointing the Finger at Him

Have you ever felt like the man you are seeing just can’t do anything right? Even when you take the time to explain how you want things in a gentle way so you don’t hurt his ego. Still, nothing… How can this be? Does he really not care? Does he not want to make you happy? Is he incapable of thinking past himself?

This is one of the great mysteries about men for that women graple with.  I haven’t quite figured this out yet. But, let me share with you how I helped one of my dating coaching clients this week with this problem.

Patty has actually been in a relationship for 4 years. Coming up on their fourth anniversary, Patty didn’t want to relive the previous time markers as they had been very unsatisfactory. Tim had forgotten the first year. The second year, Patty made a dinner reservation. The third year they didn’t do anything and coming up – year 4.

This lack of acknowledging an important milestone hurt Patty and left her feeling unloved. Yet, it was very confusing because she knew in her heart that Tim did love  her. So what is the story?

Overall, Patty is both unhappy AND happy with Tim. She appreciates the love, the snuggling, the support, but Tim isn’t as social or talkative which tends to bring Patty down. Is he the wrong man for her?

Not sure about that. Looking deeper into things, Patty is unhappy with her life. She had lost some long-time friends do to them moving away and natural attrition. Her job is very stressful and in perimenopause, she’s more emotional than she ever was. When Tim comes home from his day, she looks to him to fulfill her high level social needs – which is not in his nature.

And then we have the anniversary fiascoes building up. He had promised year 4 would be different and he didn’t come through.

As we continued to talk, it came to me that Patty might be dumping all of her unhappiness and life disappointments on to Tim’s shoulders. Now it’s true, he’s not good with anniversaries and who knows why. But when Patty looks at things objectively, she doens’t want to leave Tim. She likes his even-tempered nature, his reliability and his totally trustworthiness.

Even though Patty had started to look at apartments, thinking the only solution is to move out, through our dating coaching discussion, Patty started to consider another option based on this foundational thought:

Tim is not responsible for her happiness or her entertainment. She is.

Patty needs to do something to turn around her life. To make it richer, fuller, more satisfying and fun-filled. She needs some new girlfriends and interests. She needs to exercise and manage her stress. She needs to stop this train before she dumps a guy she does love.

Sometimes when we put more and more pressure on a man to deliver, he resists even more. Is this stubbornness? An uncaring nature? Or an energetic principle at work, based on the Law of Attraction,  that manifests in a man’s resistance? I’m leaning towards the latter. Like attracts like, so criticism might attract…more things to criticize…

Before Patty throws Tim out with the bath water, so to speak, she agreed to pull back, stop picking on him for everything and work on herself. This is very wise. You can never go wrong with this as your focus until you get more clarity.

This wasn’t the easiest dating coaching session I ever facilitated, but it could be the start of a transformation for Patty that shifts her life, her perspective and possibly her relationship with Tim. As her dating coach,, I’m rooting for her all the way.

photo credit: Adam Crowe

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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