Dating Over 40: Flirting is Spontaneous – Stop Over Thinking!

How do you know if you are over thinking flirting? If you have to ask yourself the question, the answer is most likely, yes you are. Flirting should be spontaneous. If you’ve been planning what to say for some time now, you are guilty of over thinking.

Flirting works best when you make comments off the cuff. The spontaneous, creative nature is what makes flirting fun! Scripting and planning may help the novice get started, but that’s now where you want to stay with the process. If you do, you will not likely have the success you hope for.

Some level of confidence is required to make flirting feel natural. Build your confidence and you will automatically improve your flirting skills. That’s why flirting is best practiced with no one in particular as the target. Take the pressure off and give yourself permission to try small steps. Rather than starting off with the hopes of a big conversation, just make a quick comment and walk away. That is often much easier to accomplish for shy folks.

If you are dating after divorce or over 40, and still wondering whether or not you are stuck in your head, here are a few signs that you are probably over thinking flirting:

1. You already figured out that you’ll be rejected if you try to start a conversation
This is such a common pitfall and is the result of worry regarding rejection. Why not reject yourself first to save yourself the embarrassment right? But its a sign you are in your head and are making up stories about what will happen. The truth is, you have no idea what will happen until you give it a try.

2. You have stories in your head about why the person might not be interested
As in reason #!, there is no true evidence that you will be rejected. This is the nonsense that rules your mind. Its a common coaching issue and often people need to decide who will be in charge of their brain and life. That gremlin voice or your authentic self? Believe it or not – they are not the same thing. That nasty voice will try to keep you safe and hold you back. Learn to ignore the negative inner chatter, be gutsy and go for it!

3. You are so in your head that you’ve been thinking about this for weeks (or months) but have yet to utter a word to any man.
If you’ve been spending more time thinking about connecting with someone rather than actually doing it – that’s a sure sign you are over thinking! Find a way to be more spontaneous, take a chance and just say something! Break the ice and get it over with so you can move on to getting to know the person.

4. You’ve picked out one special person as the sole recipient of your flirting
This can be the core reason why you are not moving ahead with flirting. Having your eye on a particular person can build up the situation and make it seem like a huge risk. After all, you can think about it forever and avoid getting rejected that way.

Instead, practice your flirting in every day situations as they crop up. Waiting for the perfect opportunity could mean you’ll be waiting a very long time. And that won’t get you any where!

If you are dating after divorce or dating over 40 (or at any age), give yourself permission to possibly mess up. So what? It may take a few tries before you get comfortable with flirting spontaneously, but you will build confidence the more you do it.

Confident people are more attractive, so your efforts will be well worth it. Even if you don’t hit it off with one person, by flirting and being more friendly with many people, you open up plenty of new opportunities! To find love over 40, that is the name of the game. The more people you meet, the more likely you are to find the one who is right for you.

There is no shortage of people to flirt with. The only shortage is your willingness to give it a go. Stop hanging back and start taking the risk to try it. Spin the wheel of life and take a chance. I guarantee you’ll be enjoying yourself before you know it!

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.

1 thought on “Dating Over 40: Flirting is Spontaneous – Stop Over Thinking!”

  1. I have exactly what you are describing here, but I am not going to call it over-thinking.
    I prefer Attention Deficit Disorder. The buzz phrase over thinking has been abused by motivational speeker in the workplace, which could identify people with AD/HD. Making it a Federal crime under the American’s with Disabilities Act. The people you are targeting are disabled and should seek professonal help on an individual basis. By the way you forgot to mention the nasty chemicals the brain dumps into these people, which is the true reason they are shy. You should have it if you talk about it. Keep up the good work.


Leave a Comment