How to Stay Positive – Why Dating Is Like Shoe Shopping

How to stay positive while dating is a challenge countless women deal with. It’s not easy. But this fun analogy about shoe shopping will surely help!

how to stay positiveMen and Shoes – An Unlikely Pair

I know this sounds like a crazy idea, but hang in there while I explain to you why dating is like shoe shopping.

I had lunch with my friend Fern this week. She’s a skilled hypnotherapist, quite a character and tells a great story. Of course, the subject turned to dating (I never stop) and she shared this idea from a great article she wrote years ago.

This thought-provoking comparison is really good! And my hope is that it’s one of the best ways of how to stay positive about dating.

Why Dating Is Like Shoe Shopping

When you go out shoe shopping, maybe to Macy’s or DSW, you walk around looking at everything on display. You might need a basic black heel, but that never keeps you from trying on all sorts of shoes right?

Shoe shopping is such a unique experience because just about everybody can wear great shoes. Stylish, designer, funky, comfy or practical. There are so many options!

You gather up the shoes you want to try on and imagine how they’ll look when the sales person goes off to find your size. You wait with great anticipation. Returning with an armload of boxes, the fun begins.

When the Shoe Doesn’t Fit

Sometimes the pair you want most, the super hot, stylish shoe with a fabulous heel and wonderful detail, doesn’t fit! It hits you in the wrong spot, is too tight, or doesn’t have enough support. Whatever the issue is, your dreams of this perfect shoe that is so adorable are completely dashed.

Does that keep you from trying on the next pair? No way! On to the next! And the next. I’ve been shopping sometimes and have tried on eight pairs or more. All sorts of crazy, fun shoes with heels too high, or flats I’d never wear but, are so adorable.

That’s part of the fun isn’t it? Pushing yourself to new limits? Imagining what a shoe would go with in your closet. Or being willing to build an entire outfit around a shoe that doesn’t go with anything in your closet. But you love it so what the heck!

On occasion. you find a shoe that’s like a fairy tale. It’s gorgeous and comfortable. You don’t ever want to take them off. You feel sexy and imagine how you’ll look walking into the party or restaurant wearing those heels. You’ll wear them for years – you are so sure.

When a Man Let’s You Down

Say you meet an amazing man. He is so handsome, charming and smart. You go out on a couple of dates, but sadly discover he can’t seem to talk about anything but himself. He barely asks you even one question.

How could a man who seems so good “on paper” be so wrong? He’s sure not the good fit you dream of. He is like those designer shoes you really hoped would fit. Too bad they felt like cardboard.

Does that stop you from looking for more shoes? Never! Onward to the next retail outlet. Even if you’re shopping on Zappos and return every pair, you are most likely to visit the website again and buy another pair right?

Why Do You Give Up on Men, But Not Shoes?

Why, when you meet a man who doesn’t work out, do you immediately want to give up?

Have you ever bought a pair of shoes that felt good in the store, but after wearing them for a while your back or feet hurt? Or both? It’s a major bummer. You sunk some hard-earned cash into those shoes. Your hopes of looking totally hot crumble and you feel crushed, it’s true.

Does that keep you from looking for more shoes? Does it prevent you from staying positive about shoes? Nope, no way. Before you know it, you are back in the market, optimistically seeking a new pair to replace them.

Negativity about Men

But, if you go on three dates or see a guy for three months and things don’t work out, you want to give up. Maybe you think all men stink so why bother? There are no good men out there anyway. Or you insist, “Never Again!”

That’s why Fern’s analogy is a pretty good, even if it is rather unconventional and surprising. She makes an excellent point and this could very well be the answer to how to stay positive about dating and finding love.

Don’t Give Up – Look for a Replacement!

When your favorite shoes let you down, you look for a replacement. You don’t get downtrodden, insist shoes have let you down, and decide to forgo new shoes for the rest of your natural born life.

Now I realize shoes are not men or love. (Well that’s not exactly true about the love part.) But, you can learn an important lesson about dating from your relationship with shoes.

How to Stay Positive about Dating

Here’s an important lesson about love from your shoes. Looks and style can be deceiving. When your shoes disappoint you because they wear out quickly or aren’t as comfortable as you thought, its a bummer. But, not crippling. Why is that?

I think it’s because you know there are MORE shoes to be tried on until you find the right fit and style. Or at worst, there will be a new season and styles will change. That’s the basis of how to stay positive about shoes right? Trouble is, you don’t feel this way about men.

There Are More Men!

Just because one man doesn’t work out, disappears or breaks your heart, doesn’t mean you should swear off all men. There are more where he came from if you would only go look. Sure, take time to get over it and heal. However, do not let it roll into many long months or years. (Like the 18 years I wasted from 22-40, yes, my entire youth.)

No one enjoys getting heartbroken by amazing shoes or a love interest. But, you can and will recover and you can find another. If you have a bad date, shake it off. If you have a bad three month relationship and the guy ghosts on you, shake that off too.

Don’t give away your hopes of love and your power to take charge of your life, to the man who let you down. When you quit, he wins! This is why you want to learn how to stay positive about dating – to try again!

I Want You to Win at Love

I want you to find love. You deserve love. I’m a firm believer that love is your destiny. Women fall in love every day. You can too if you…don’t give up.

Keep going. Get a new pair of shoes and pump yourself up. Build your confidence. Find some optimism. Come up ideas on how to stay positive and active. Renew your conviction and commitment to find love. That’s what it takes and it’s WORTH IT.

Then go look for the man who will look great on your arm while wearing those hot shoes.

Thanks Fern. To learn more about her work visit her website.

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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