Dating Over 40: Am I Just Lucky to Have Found a Great Woman So Fast?

Let me tell you about my dream client Fred, who is 64 and recently widowed. He is a good looking man on the short side – 5’7", in good shape and still working out, with some coin, who makes easy conversation and has a sense of humor.\

Fred came to me because he hadn’t dated in more than 40 years and wanted to know what he was getting into. Naturally he was looking forward to meeting lots of women and playing the field for a while. After 40 something years, who could blame him? It sounded like a lot of fun to him and Fred said – there are so many good looking women to choose from with a sparkle in his eyes.

Wanting to know where to look for women, what to expect when dating, what women are looking for, Fred and I talked about EVERYTHING. Believe, I  mean everything. He is really sweet and you can tell he’s romantic too..I told Fred that he didn’t have much to worry about, cleared up quite a few misconceptions about dating today and then assured him, he’s a VERY HOT COMMODITY. 
I helped Fred come up with places where he could meet women. He decided to take up ballroom dancing which I thought was a great option for a man – there are  so many women into ballroom. Plus, I knew in the back of my mind that a widower of 64 would be getting fixed up by his women friends left and right. Fred wasn’t sure about this, but I was quite certain.

Our first meeting was the last week of September.  Fred had been fixed up and gone out on a couple of first dates. Plus he had started to get up the nerve to ask women out that he met at charity events and elsewhere. Like most older men, he was even hoping to date some younger women.
He met one nice enough woman in Boston, one in Long Island, one from Manhattan. I give the guy credit for being willing to get out of the local area and just meet people! The Long Island babe emailed him after their first date to invite him to a charity event she was planning to attend. This didn’t go over big at all. Fred told me he couldn’t go anyway because he was traveling, but he didn’t like her aggressive move. He also told me he wasn’t too into her anyway. Hold that thought.
The next meeting he had a few second and third dates to talk about and a few more first dates as well. Fred was really percolating along. He asked lots of really smart questions about meeting people, understanding who is right for you, wondering what to look for and how to tell if someone might be a good match. We talked about how to let a woman off the hook gently, when he could think about having sex, and plenty more.
I just met Fred for our third meeting and was quite surprised by his progress. He is still going out on a first date here and there, but told me that he had called Ms. Long Island (who is 62) again and went to visit her . I guess he had changed his mind about not being that into her –who knows what twist of fate caused that shift.
Things just seemed to click and she suggested he stay over since it was a long trip back to CT. (Nudge nudge wink wink.) he ended up in her bed and was immediately smitten. They have had three additional dates since then and now he is planning Valentine’s Day and maybe a short trip to Mexico to use up an expiring plane ticket.
Don’t we move fast? Fred isn’t quite willing to give up his freedom yet though and neither has said a word about exclusivity. But Fred did say that being with Ms. Long Island is so natural and surprisingly easy. they have a similar background but really do come from very different worlds. She is so easy to get along with, seems to like what he likes, appreciates what he does and doesn’t seem to expect much. (No pressure yet from her about anything…)
Yet, he was going on a second date that very night. Fred did admit that he was no longer pursuing any new opportunities unless they came up and bit him, he wasn’t planning any more first dates. But he wondered whether he had to be exclusive yet. That’s when he asked me, "Am I just lucky to have found someone so quickly who really seems to fit the bill?"
I explained to Fred that he was twice lucky. First because he found someone that seemed like a good match quickly. Second, because he had managed to completely miss out on meeting any crazy ladies – which, come on, we know are out there too. So Fred was twice blessed.
You could see that he had hoped his dating journey would take a bit longer and he was bummed that his swinging single days might already be coming to a close. But on the other hand, Fred was smart to realize that balancing several women at the same time sounded like more fun than it was.
The end of the conversation focused on how he could tell if Ms. Long Island was the right one for him. I suggested that there was no hurry. Fred should be willing to continue data gathering about her and watch for their first disagreement because this will give him insight into how they will resolve the inevitable issues that crop up in every relationship. And since he is still data gathering, don’t go too big on the Valentine’s day gift and no red roses – wait until you are really sure before you go there.
He wondered how much longer this might take to really know and I said any where between six months and a full year. many experts say you need to go through four seasons with someone to be really sure which I think is very solid advice. But, I’m sure he’ll know long before a year of how incredibly lucky he is to have found a woman like Ms Long Island.
And not surprising about a widower from a happy marriage – they often manage to find someone quite right away, not wanting to be alone. I wished Fred all the best and sent him on his way as I told him that my door and phone are always open should he need any more dating advice.


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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