You've chosen the dating app.

You've written the profile.

You've found some recent photographs where you look recognisably like yourself.

You've even resisted the urge to use the one from 2014 where the lighting was particularly kind.

And then it happens.

You match with someone.

Excellent.

Now one of you has to actually say something.

You stare at the little message box.

They seem interesting.

You'd quite like them to reply.

And the best you can come up with is:

Hi.

Welcome to the next stage of online dating.

If you're still sorting out your profile before you get to this point, start with How to Write a Dating Profile After 50 That Actually Sounds Like You.

Is There Anything Wrong With Saying “Hi”?

No.

But you're making the other person do all the work.

Hi.

Hi.

How are you?

Good thanks, you?

Good.

And there we are.

Two potentially fascinating human beings have managed to create a conversation with all the excitement of waiting at the Post Office.

The easiest way to get a better conversation going is to give somebody something they can actually respond to.

Start With Their Profile

This is why I keep saying your dating profile needs little conversation hooks.

Use theirs.

Perhaps they've mentioned:

• a recent trip

• a favourite place

• a hobby

• live music

• cooking

• walking

• a dog

• something funny

• somewhere they'd love to visit

You don't need an incredibly clever opening line.

You just need to show that you've actually read their profile.

Instead of:

Hi, how are you?

Try:

You mentioned you love Italy - whereabouts is your favourite place? I've got a weakness for little Italian towns and coffee myself.

Or:

I saw you're a live music fan. What's the best gig you've ever been to?

Or even:

I have to ask about the dog in photo three. Yours, or have you borrowed one for dating-profile purposes?

Now there's somewhere for the conversation to go.

Ask Questions That Don't Feel Like an Interview

Questions are good.

An interrogation isn't.

There's a difference between:

Where do you live?
What do you do?
How long have you been single?
Do you have children?
What are you looking for?

and an actual conversation.

Imagine you're chatting to somebody you've just met at a party.

You wouldn't normally fire six questions at them without offering anything about yourself.

So instead of:

Where did you go on holiday?

you could say:

That photo by the sea looks gorgeous - where was it? I keep saying I'm going to explore more of Italy rather than returning to the same places.

You've asked a question and given them something about you.

That's conversation.

Don't Send an Essay

The opposite problem also exists.

You match with somebody.

They say:

Hi, how's your weekend going?

And in response they receive your life story from 1987 to the present day.

Including your divorce.

Your children's careers.

The loft conversion.

And an unexplained dispute with somebody called Sandra.

You don't need to tell somebody everything immediately.

Let the conversation unfold.

A couple of sentences is plenty at the beginning.

If they're interested, they'll ask more.

Give Them Something Back

One of the quickest ways for a conversation to die is this:

What do you enjoy doing at weekends?

Walking.

Anywhere in particular?

Countryside.

Do you have a favourite place?

Malvern.

At this point, the other person isn't chatting.

They're conducting an interview under increasingly difficult conditions.

If somebody asks you a question, answer it - but give them something back.

For example:

I love walking around the Malvern's, particularly when the weather's decent. I'm always much more enthusiastic if there's a pub at the end though! What about you?

Same information.

Completely different conversation.

You Don't Have to Reply Immediately

This is something online dating has changed.

Years ago, if somebody telephoned and you weren't home, they simply couldn't speak to you.

Now we're all apparently available all the time.

A message arrives.

You see it.

You don't answer for three hours.

And suddenly you're wondering whether they'll think you're not interested.

Or you're watching:

Online 7 minutes ago.

👀

Don't do that to yourself.

People work.

They see friends.

They look after grandchildren.

They go shopping.

They fall asleep watching television.

They put their phones down.

A dating app should fit into your life.

Your life shouldn't start revolving around the dating app.

But Don't Play Games Either

There's a difference between having a life and deliberately waiting seven hours because somebody once told you it makes you look more desirable.

If you want to reply, reply.

If you're busy, reply later.

If you're interested, it's okay to look interested.

You don't need a strategy involving stopwatches.

Flirting Is Allowed

We're dating.

Not arranging somebody's boiler service.

You don't need to become outrageously suggestive, but a little warmth, humour and playfulness can change the whole tone of a conversation.

A compliment can be lovely when it's genuine.

You have a really warm smile.

You made me laugh with that bit in your profile.

I like your outlook on life.

Those tell somebody what caught your attention without immediately making the conversation sexual.

And if flirting feels like a language you've completely forgotten, I've got a free Flirting Guide to help you get back into it.

Don't Make It Sexual Too Quickly

This is particularly important when you haven't established that the other person welcomes it.

There's playful flirting.

And then there's:

Hello Susan, nice photograph. What are you wearing in bed?

Susan has not even finished her cup of tea.

Calm down, Trevor.

Sexual comments very early on can make somebody uncomfortable incredibly quickly.

Let the tone develop between you rather than deciding for both of you where the conversation is going.

What If You're Always Starting the Conversation?

Pay attention to effort.

You don't need to keep score:

I sent 3 messages, they've sent 2.

But over time, conversation should feel reasonably mutual.

If you're always:

• starting it

• asking the questions

• keeping it alive

• suggesting things to talk about

and they mostly respond with:

Haha

Yeah

Nice

you may simply be more interested than they are.

And that's useful information.

You don't need to convince somebody to be interested in you.

What If They Don't Reply?

This can sting more than we'd like to admit.

Especially if you thought you'd found somebody promising.

You send a message.

Nothing.

You wonder whether you said the wrong thing.

You reread it.

You check whether they've been online.

You consider sending another one.

Sometimes there will be a perfectly innocent explanation.

Sometimes there won't.

But somebody not replying doesn't automatically mean there is something wrong with your message, your photographs or you.

They may be talking to somebody else.

They may have changed their mind.

They may have deleted the app.

They may simply not feel the connection.

Online dating gives us access to far more people than we'd encounter in everyday life - but it also means we'll experience more little moments of rejection.

Try not to turn every unanswered message into an investigation.

When Should You Move From Messaging to Meeting?

If the conversation is flowing, you don't necessarily need to spend three weeks becoming pen pals.

The point of online dating is eventually to discover whether you actually enjoy being together offline.

You might say:

I've really enjoyed chatting with you. Would you fancy carrying this conversation on over a coffee sometime?

Simple.

No grand declaration.

No enormous first date.

Just:

Shall we meet?

And because you're still meeting somebody you don't actually know yet, make that first meeting somewhere public and tell somebody where you're going.

Before you arrange that first date, have a read of Online Dating Safety After 50. It covers staying on the dating app at first, spotting pressure and warning signs, protecting your personal information and meeting somebody safely for the first time.

Before You Meet - Remember You're Choosing Too

It's very easy to become focused on:

Do they like me?

But you are not trying to win somebody.

You're finding out about each other.

Do you enjoy talking to them?

Do they seem interested in you?

Do you feel comfortable?

Are you curious enough to meet them?

Would you like another conversation?

That's all you need to know at this stage.

If you find yourself choosing people based on the same very specific checklist you've always had, you might also enjoy Date Outside Your Type.

Haven't Chosen a Dating App Yet?

Perhaps you've read all this and thought:

That's lovely, but I haven't even joined one yet.

I've compared OurTime, Match, eHarmony, Hinge and Bumble in my guide to the Best Dating Sites & Apps for Over 50s in the UK, including the sort of dater each might suit.

Then once you've chosen one:

How to Write a Dating Profile After 50 will help with the words.

Dating Profile Photos After 50 will help with the pictures.

And this guide will still be here when somebody finally says hello.

And If Apps Aren't Your Thing...

That's okay too.

Online dating is a tool.

It's not compulsory.

You can meet people through activities, friends, hobbies, travel, singles socials and simply getting out into the world.

If you'd rather start face-to-face, have a look at Singles Events Near You.

Or if you're not even sure what stage of single life you're at yet, take my free What Type of Single Are You? quiz.