Dating Over 40: You Don’t Have to Feel Confident Before You Start Dating

Mistake #9

In the series of The Biggest Mistakes Singles Make When Wanting a New Partner

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“I’ll start dating when I feel more confident.”

It’s something I hear surprisingly often.

Sometimes it’s:

“I haven’t dated for so long, I wouldn’t know what to do.”

“I need to work on myself before I meet someone.”

“I don’t think anyone would be interested in me at my age.”

So dating gets put off.

For a few months.

Then perhaps another year.

And sometimes several years.

Because we’re waiting for a magical moment when we suddenly wake up feeling completely confident, attractive and ready to put ourselves out there.

Unfortunately, confidence doesn’t usually work like that.

Often, confidence comes after we start doing something — not before.

Dating again can feel daunting

If you’re dating over 40, 50, 60 or beyond, there’s a very good chance the dating world looks quite different from the last time you were single.

Perhaps you met your previous partner before dating apps existed.

Maybe you’ve were married for 20 or 30 years.

You might not have been on a first date since your twenties.

And suddenly you’re expected to create an online dating profile, choose photographs of yourself, message strangers and somehow know what all the unwritten rules of modern dating are.

Of course that can feel daunting.

If you’re dating after divorce, separation or bereavement, there can be another layer too.

You aren’t simply learning how to date again.

You’re learning who you are as a single person.

It would be surprising if you felt completely confident from day one.

Confidence is built by doing

Think about almost anything else you’ve learned in life.

Driving.

Starting a new job.

Walking into a room where you don’t know anybody.

Going to the gym for the first time.

You probably didn’t wait until you felt completely confident before doing it.

You did it feeling nervous.

Then you did it again.

And eventually, it stopped feeling quite so scary.

Dating can be exactly the same.

Your first conversation with someone new might feel awkward.

Your first date may feel nerve-racking.

You might spend far too long deciding what to wear.

But then you’ve done it.

The next time, you know what to expect.

And little by little, you begin to think:

“Actually, I can do this.”

That’s confidence.

Not the absence of nerves.

The knowledge that you can do something even when you’re nervous.

“I’ll lose weight first…”

This is one I hear particularly often when people are thinking about dating later in life.

They don’t feel attractive enough yet.

Perhaps their body has changed.

They’ve gained weight.

They don’t look exactly as they did the last time they were dating.

And so they decide they’ll put themselves out there once they’ve lost a stone, joined the gym, updated their wardrobe or generally become a “better” version of themselves.

There’s absolutely nothing wrong with wanting to feel good about yourself.

If exercising, eating differently or buying clothes you love makes you feel happier and healthier, wonderful.

But don’t make being a particular size the entry requirement for being loved.

The person you’re hoping to meet isn’t 25 either.

They’ve lived.

Their body has changed.

They have wrinkles, scars, insecurities and things they’d probably change about themselves too.

You don’t need to become perfect before you’re worthy of meeting somebody.

You just need to be willing to be seen.

You don’t need to have everything sorted

Another version of this is:

“I need to work on myself first.”

Sometimes that’s absolutely true.

If you’re dealing with the immediate aftermath of a painful breakup, struggling emotionally or simply know you’re not ready for a relationship, taking some time for yourself can be incredibly important.

But “working on yourself” can also become something we never quite finish.

There’s always something else we could improve.

Another book to read.

Another goal to achieve.

Another few pounds to lose.

Another area of life to sort out.

You don’t have to become the finished version of yourself before you find a partner.

None of us ever really are.

A healthy relationship isn’t a reward you receive once you’ve successfully completed all your personal development.

Confidence can take a knock after divorce

For people dating after divorce, particularly if the end of the relationship wasn’t their choice, confidence can understandably be fragile.

Rejection hurts.

If somebody you expected to spend your life with no longer wants that relationship, it’s very easy for their decision to become tangled up with how you see yourself.

Was I not attractive enough?

Interesting enough?

Loveable enough?

But the ending of one relationship doesn’t determine your value to somebody else.

The next person isn’t your ex.

They’re meeting the person you are today, without all the history and baggage that existed within your previous relationship.

Allow them to make up their own mind about you.

You may be far more attractive, in every sense of the word, than you’ve allowed yourself to believe.

Dating after bereavement can affect confidence too

For somebody dating after bereavement, confidence can be affected in a different way.

You may have spent decades knowing you were loved.

Then suddenly you find yourself single in a world you never expected to re-enter.

It can feel strange to think of yourself as somebody who dates.

Even the idea that another person might find you attractive can feel unfamiliar.

There may be guilt too.

But wanting companionship again doesn’t take anything away from the relationship you had.

And you don’t have to know exactly how this next chapter will look before taking the first small step towards it.

Don’t compare yourself with everyone on dating apps

If you’re using online dating or dating apps, confidence can take another battering.

You’re surrounded by photographs of other singles.

People who appear more attractive, younger, fitter, more successful or more interesting.

Remember, you’re looking at their shop window.

Their best photographs.

Their carefully selected interests.

The version of themselves they’ve chosen to present to strangers.

They’re probably looking at other profiles and comparing themselves too.

You aren’t competing with every other single person online.

You’re looking for the people who will appreciate you.

And you won’t be everybody’s cup of tea.

Nobody is.

You don’t need to be.

Start smaller than “finding a partner”

Sometimes the goal itself creates pressure.

“I need to find someone.”

That’s enormous.

What if instead your goal was simply:

I’ll have a conversation with someone new.

Or:

I’ll let my friends know I’m open to being introduced to somebody.

I’ll go to an event where I might meet new people.

I’ll agree to one date.

I’ll speak to a professional matchmaker and find out what my options are.

You don’t need to leap from being happily at home on your sofa to searching for the love of your life overnight.

Take one small step.

Then another.

You may need somebody to believe in you before you do

This is actually one of the parts of professional matchmaking that I don’t think gets talked about enough.

Yes, my job is to introduce people.

But it’s also to support them through the process.

Sometimes a client can’t see what I can see.

They focus on their age, their weight, their nerves or the fact they haven’t dated for years.

I see the warmth when they talk about their family.

The passion when they tell me about something they love.

Their sense of humour.

Their kindness.

The interesting life they’ve lived.

The things another person could find incredibly attractive.

Sometimes we need somebody else to remind us of those things until we start seeing them ourselves.

Don’t wait until you’re fearless

If you’re looking for love after 40, 50, 60 or beyond, you don’t have to feel completely confident before you begin.

You can be nervous and excited.

Hopeful and terrified.

Ready and unsure.

All at the same time.

Confidence isn’t something you have to find before you start dating.

It’s something you can build along the way.

So if you’ve been telling yourself:

“I’ll do it when I feel more confident…”

perhaps change the sentence.

“I’ll do it even though I don’t feel completely confident yet.”

Send the message.

Accept the invitation.

Have the conversation.

Go on the date.

Ask for help if you need it.

You don’t have to take a huge leap.

Just take the next small step.

Because perhaps the confidence you’ve been waiting for isn’t something you need in order to start.

Perhaps starting is exactly how you’ll find it.

Your regular dose of genuine advice, real-world dating tips, and confidence-boosting reminders that love is never out of reach. Whether you’re diving back into dating or just dipping a toe, think of this space as your encouraging nudge, your friendly cheerleader, and your go-to guide for doing love the grown-up way.