Dating Over 40: What if He’s Not as Cute as You Thought?

Dear Dating Coach, 

You know how when you meet some people in a bar/club/restaurant that’s dimly lit and then they leave and go out into the light with the person who ends up looking a little different? It’s kind of funny but it’s true.  Well, I recently enjoyed a first date and said yes to a second before i remembered this detail.  When we exited the building, I realized my date looked a little less attractive then when we were inside in the low lighting.

So my question is:  What is your take on attraction? I like the guy and we’re going to go on another date. However, I want to know what you thoughts are about attraction and this situation. What advice, techniques, and/or suggestions can you offer me so I make sure I keep my focus where it should be.

Looking for Cutie

Dear Looking,

The best thing you can do is think about how you  FELT, rather than how he LOOKED. Since you felt good enough to say yes to a second date, let that be your focal point. Everything else is mind chatter that most likely won’t serve you.

While looks are important and so is attraction, you already experiencedenough attraction to spendquite a bit of time with the man. Plus, you said yes to a second date. How bad could he be? Sometimes over-scrutinizing or rethinking is a self-sabotaging way to keep yourself single…

From working with so many people who are dating over 40 or dating after divorce, I definitely know attraction can grow and deepen. Women in particular are drawn in by a man’s personality, especially if he has endearing qualities. We get attracted with our minds, not just our eyes.

Don’t Think Too Much
The best advice I can give you or others dating over 40 is DON’T THINK TOO MUCH! You haven’t collected nearly enough data about him to spend a lot of time thinking about him yet. When you catch yourself thinking about him, good or bad, jump the track on that thought train and move on to think of anything else you can.  

Over thinking has been the ruin of more fledgling relationships than you can imagine. It’s one of the biggest down falls for many of my dating coaching clients.

Distraction Is a Girl’s Best Friend
Especially when dating over 40 or dating after divorce, distraction can be a girl’s best friend. When you first start dating a guy, that is the time to read a new book, start a new project, plan a night out with the girls, exercise, or date other men! this helps minimize the “eggs all in one basket” syndrome of projecting into the future or over-questioning your prospect’s potential.

When stuck in the over thinking mode, women often sabotage themselves by actually making things up in their minds or placing meaning where there is none. This can be a disaster! So distract yourself and stop thinking about him.  Do whatever it takes

Hey, you’re human and all this is very normal. But don’t let it interfere with getting to know someone who has potential and could possibly be “the one”.

Hope that helps,


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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