My goal is to help you create a lifestyle of positivity and possibility. I am smiling!

– Warmly, Honey

Here’s Why Over 50’s Dating Seems So Darn Hard

Darlings, today’s blog is written by the wonderful dating and romance expert, Lisa Copeland. I know many women struggle with dating, and it doesn’t matter what age you are! However, after 50, dating can be especially difficult. Lisa helps explain why dating after 50+ doesn’t have to be so hard and how to conquer that fear! I do hope you enjoy her great advice. 

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Ever wonder why dating feels so hard?

I believe it’s because most women see dating as an activity they must endure versus enjoy.

I know from my own life that dating is not such a joyful experience when you’re trying to figure out in three minutes or less whether he’s the one.

You go on a date geared up to interview him as you mentally check off the boxes on your imaginary “must-have ” checklist to see if he fits.

Putting The Pressure On 

Dating this way puts so much pressure on you and ultimately leaves you feeling like there’s no one out there to date. Yet there are millions of men and women looking for partners every day, so what’s going on?

Why can’t men and women find each other?

They are dating to mate as they did in their 20s when women were looking for the right man to make babies with. Today as a woman over 50, you have way more options for how a man fits in your life than you did back then.

He can be:

    • A companion for events like weddings and office parties
    • A partner in a committed relationship with whom you live
    • A partner in a committed relationship who lives in his home while you live in yours
    • A friend
    • A lover
    • A boyfriend
    • A husband
    • A significant other for lots of two-to-seven-year relationships you enjoy until you outgrow each other

Times Have Changed 

Today, you have so much freedom and choice that you didn’t have in your 20s. 

And when you adopt this mindset change for over 50s dating, it will free you from the outdated way of only dating to mate for a husband.

How Do You Date? 

So how do you date when you’re dating for fun or for a relationship?

Well, instead of trying to figure out if he’s the one in 3 minutes or less, try asking fun questions like:

    • What was your favorite game growing up?
    • Did you have a favorite TV show growing up?
    • What was your favorite music growing up?

Nostalgic questions create a bond and probably lots of laughter as you share memories to which you can both relate from your childhood.

These types of questions give you a glimpse into a man’s personality, which can make him far more interesting and a lot more fun.

Perceived High-Value Qualities

The other reason dating can make you feel so miserable is when you go out in the dating world looking for a man who has what I call Perceived High-Value Qualities.

These are specific qualities you want in a man that you think will make you happy. Examples of this: he has to be fit, eat a certain way, or he has to have a particular type of job and income.

A fit man may look good, but it doesn’t mean he’ll make a good mate for you.

The guy with the belly who could stand to lose a couple of pounds might be the guy who could light up your life every day and make you very happy if you give him a chance.

How Do You Feel Around Him? 

Instead of just using qualities as the sole basis for finding someone, think about how you want to feel around a man when you’re with him.

Because ultimately, you want to feel happy inside when you’re with the man you do choose.

And that has nothing to do with how he exercises or eats or any other so-called must-have quality. It has to do with how he treats you.

So you have some fun questions to ask and you know you have choices in the relationship you want at this time in your life. Now go out and date! 

What do you find the hardest about dating after 50? We love to hear from you! Comment below or on Facebook and Instagram


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  1. Very interesting read. I had never thought about the fact that we are looking for something different at this age then we were when we were younger. I shouldn’t say this but I really would never get involved with someone who has less income than I do. I live a certain lifestyle and wouldn’t want to downgrade. That would be the only have to have quality.

    1. I agree with you.You have your standards and stick to them. If you don’t you won’t be a happy camper. Warmly, Honey

  2. I agree that this is an interesting read, and one to think seriously about. A boyfriend, lover, or partner opens up the possibilities greatly. Being treated well by a man is more important than his income. This would be an upgrade in my life, not a downgrade by any means. This comes first, I feel.

    1. Kindness counts above all else. Money does not breed kindness. A person does. You have good values. Warmly, Honey

  3. Good article, though nothing new to me. I’ve been single, and dating, for so long I could write a book! Even though I’m not necessarily looking for another husband, I’m surrounded by peers who say *What’s the point of dating is your not maybe going to get married?”I tell them, *For fun???”

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