How to Make the First Move on an Older Woman (8 Different Ways)

Learn How to Make the First Move on an Older Woman Now

If you are wondering how to make the first move on an older woman, let’s get you started in the right direction.

Generally speaking, all women find the same traits attractive in men, and more often than not they’ll respond positively or negatively to similar situations.

With that said, we’d like to focus on improving your ability to make a move on older women in a variety of situations.

We’ll go over a mixture of principles and techniques so that you have a better understanding of what will enable your success.

How to Make the First Move on an Older Woman

Making the initial move on women that are more mature than you begins with these proven steps. Use these tips for women you meet out and about as well as those you have met online (you can see our review of the best sites to meet older women here).

1 – Make that older woman feel comfortable

Whether the move you’re going to make is asking her out, moving in for a kiss, or inviting her to your place for dinner, you need to keep in mind that she must be comfortable with you.

Your results will likely suffer if she is unable to let her guard down and feel free to connect with you.

No matter what stage you’re in, you must never forget this.

Sometimes what you need to do is talk to her more.

Other times, you may have to ask what she has on her mind.

Consider sharing a few personal things that are appropriate to the current conversation to make her comfortable with you.

2 – Pay attention to her signals

When learning how to make the first move on an older woman, never forget that she might be making a move on you, too.

Whereas a man’s first move is usually direct and to the point, a woman’s is more often than not subtle and unpredictable in nature.

Especially an older woman, who likely knows how to send signals exactly how she intends to in a sophisticated manner.

Nevertheless, don’t doubt one of the strongest signals: lingering eye contact.

You also shouldn’t doubt the personal questions, or the times she starts a text conversation with you.

In addition, sometimes her signals will be difficult to identify, but they’ll certainly make an appearance.

For example: let’s say that you just made a move to kiss her.

She politely gives you the cheek – but she still stays very close to you and continues holding your hand.

In this scenario, she’s not outright rejecting you at all.

She might just be adding further anticipation to enhance the moment when it does come.

Be persistent – but always in a calibrated way.

3 – Take the “Two steps forward, one step back” approach

To follow up on persistence, it’s important that you calibrate your approach.

This is why it’s best to think of it as taking two steps forward, one step back.

Let’s say you move in for a kiss after getting really close to her, and she politely turns you down.

Being too aggressive is likely to push her away, so instead of immediately trying again, take a step back.

Stay close to her, but return to having a warm conversation.

Avoid discussing the kiss in any way, and act as if it never happened.

In 5 or 10 minutes, try again.

If it works – don’t immediately proceed into a make out.

Keep it short and sweet, and end it before she does.

Avoid kissing her again for a short while.

When you do, make it a longer, more passionate kiss.

Two steps forward, one step back is an incredibly effective way to escalate with an older woman, so always keep this technique in the back of your mind.

4 – Don’t act aggressive or desperate 

Since this is a discussion of how to make the first move on an older woman, we must go over the essentials, and this next point is as essential as it gets.

No matter your particular circumstance at a given moment, you should always ease into making your move.

What we mean is that if you want to kiss her, you shouldn’t immediately go for a make out without some sort of build up.

And as we just mentioned, you shouldn’t be going for a full make out right away to begin with.

The key to easing into a kiss is to first sit really close to her if you’re sitting, or stand in close proximity.

Let’s say you’re sitting at a bar or a park bench, and that you have some privacy.

Ideally you’ll be at her side.

Sit close enough so that your legs are touching.

Then, you can hold her hand or caress her forearms.

Make a comment about how smooth her skin is.

If you’re sitting this close and holding on to her hand and she doesn’t flinch, chances are that you’re good to go.

But you should still ease into it further – start making deeper eye contact, while taking glances at her lips.

Maybe even brush her hair back with your fingers.

She’ll know what you’re thinking, so if she doesn’t move away, just go for it.

Put your fingers under her chin and guide her towards you.

This is a perfect example of how to ease into a first kiss.

5 – Be clear with her about your intentions

Showing an older woman your intent may be considered a first move on its own.

There’s a technique to it, and it may be something you need to work on.

Showing a woman your intent is not the same thing as telling her you’re interested in her, or that you like her some way.

When done right, being direct and showing your intent through your actions can have a powerful effect.

For instance: next time you’re on a coffee date with an older woman, practice holding eye contact longer than you’re used to.

This works remarkably well when there’s a pause in your conversation.

Hold it – just long enough so that you can feel the mutual tension.

Only look away after she does.

Don’t be afraid of the occasional silence, either.

It gives her a chance to play with the tension as well – you know you’re doing it right when she asks you a spontaneous personal question.

6 – Don’t hesitate and miss your chance

No matter what move you’re thinking of making, know that you can only lose by hesitating.

Hesitation is usually a result of overthinking and needless anxiety, which is entirely self-inflicted.

When you feel your thoughts going out of control or that you’re considering a bunch of negative (and often irrational) situations, see it as a definite sign that you’re hesitating.

Whether it’s asking her out, holding her hand, going for the kiss, or any other move you make on an older woman, know that you have more to lose by hesitating than by acting and potentially coming up short.

This is because rejection is infinitely more tolerable than regret!

7 – Take the risk and don’t overthink things

To build on the last point, remember that any first move you make is essentially a risk.

A risk that you owe yourself to take.

Otherwise, how else are you to succeed?

Anything worth gaining involves risk, and if you’re not ready to gamble, you’re not ready to succeed, either.

Generally speaking, women reward bold behavior in men (especially older women), if the actions remain respectful.

They expect you to make the first move – to act, and to not hesitate.

You have more to lose by being passive than you do by being “sensibly” aggressive.

Women will forgive you if you try and come up short – but they’ll never forgive you when you’re indecisive.

Since we’re discussing how to make the first move on an older woman, know that there will always be some risk involved.

But that’s okay, because overcoming risks is the only way to succeed.

Reflect on your actions afterwards, instead of lamenting over what could have been.

8 – Ask her out on a date

The first move can mean a variety of things – but it’s almost universally agreed that asking a woman out on a date is the definitive first move.

It’s much more indicative of her interest level when she complies to you asking her out, as opposed to her giving you her number.

Moreover, how you ask her out will depend on your initial conversation or interaction – did you meet her at a bar, at a social event, at work, or through online dating?

Many times you’ll ask an older woman out through text.

In this case, after you’ve chatted with her for a little while and you’ve established some comfort, simply ask her out:

“By the way, what’s your schedule like later this week? Maybe we can meet for a coffee, or a drink.”

If you don’t ask, your chances of seeing her are exactly 0%.

By asking, you’re giving yourself significantly better odds of moving towards a positive result.

In Summary – How to Make the First Move on an Older Woman

1) Make her comfortable

2) Pay attention to her signals

3) Two steps forward, one step back

4) Ease into it

5) Show her your intent

6) Don’t hesitate

7) Take the risk

8) Ask her out

One Response

  1. Andy

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