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How to Make the First Move on an Older Woman (7 Different Ways)


Learning how to make the first move on an older woman isn’t the easiest thing in the world. Lots of guys are naturally confident when they do this. But for the most part, learning how to approach is something you learn with a lot of practice and rejection. But keep in mind that with rejection and all the effort you put in comes the skill to get women to be more interested in you.

If you’ve got your eyes set on a sexy older woman, we can’t blame you. Mature women exude an air of confidence and sophistication that you often won’t find in younger ladies. So if you want to learn 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.

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Signs She Wants You to Make a Move

There are many signs she wants you to make a move. Some are extremely subtle that only the keenest observer can see them. Other signs, however, are much more obvious if you know what to look for.

They include: asking you questions, sharing personal information about herself, unnecessarily touching you, telling her friends about you and mentioning places she likes to go. If you see any or several of these, it may well be time to make the first move. Our list of the top 10 signs she wants you reveals more.

How to Make a Move on an Older Woman

Making the initial move on women who 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).

Make sure she has noticed you

To give yourself the best chance of success, you need to first make sure she has noticed you. Search for some kind of sign that she wants you to make a move or is curious about you.

If she’s showing you a bit of attention, then you’ll feel more confident about approaching her, and it’s more likely to go well. This is especially true if you're at a place where it's easy to meet older women.

So, how do you know if she’s noticed you? She’ll likely do a few of the following:

  • Make eye contact
  • Smile at you
  • Stand near you or face her body towards you
  • Flirt with you
  • Strike up (or engages in) conversation with you
  • Laugh at your jokes

Older women tend to be clearer and more forward with their intentions. So if she’s interested in you, she will probably display a few (or all) of the signs above. This is your invitation to give her some signs back.

And if she hasn’t yet shown interest, why not be the one to strike up a conversation and see what happens?

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How to make the first move by making her comfortable

In order to move things forward with any woman, it's usually not enough for her to just be attracted to you even if you're younger. She also has to be comfortable with you.

Essentially, this means she has to trust you, feel safe around you and notice an emotional connection with you. Most importantly, she has to believe you have her best interests at heart.

You might think that this is less important to a savvy older woman with a bit more life experience. If anything, she has probably grown mature enough not to make decisions based on pure attraction. In this stage of her life, emotional connections are likely to be more important to her. She's probably run off with enough players who didn't give a damn about her.

It takes time to make women feel comfortable around you. But you can speed up that process by sharing deep emotional stories you wouldn't tell to “just anyone.” In fact, any behavior that demonstrates she's not just “the next woman” will be helpful.

If she starts to share similarly personal tales, that's a sign she feels comfortable in your presence. It also helps if you're in a place where she feels comfortable as an older woman talking to a younger man.

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

Pay attention to her signals

When learning how to make a move on an older woman, it's important to be able to spot when she wants you to push things forward.

Women will show signs they're attracted to you, but they're likely to be more subtle than the signals a man would make.

This is especially true with older women. Where a younger woman might be carefree enough to throw her arms around you and stick her tongue down your throat, an older woman tends to send more sophisticated indicators of interest through her body language. These moves can be as subtle as holding lingering eye contact, asking personal questions or moving unnecessarily close to you.

It's also common for an older woman to lightheartedly play down the chances of anything happening between you. Perhaps she teases you verbally or politely gives you the cheek when you make a move to kiss her. Make a note of the sub-communications when she pulls moves like these. Is she still smiling? Is her body language still relaxed? Often, in these scenarios, she's not outright rejecting you at all. She might just be adding further anticipation to enhance the moment when it does come.

At the same time, she may want to see how you react to these small rejections. Does your confidence waver or do you remain in a self-assured mood? If you can remain sure of yourself, even without her showing obvious signs of attraction, this can prove to be incredibly attractive.

Take the "two steps forward, one step back" approach

Most women really enjoy the "will we, won't we" nature of flirting with a new man. So, you need to learn how to play this game when you pick up older women without getting too frustrated. If she does pull away when you go for a kiss, you need to not let it bother you.

Also, she'll appreciate it if you keep her guessing with any moves you make on her. Think of it as a "two steps forward, one step back" approach. If she allows you to kiss her, don’t immediately proceed into a full-blown make-out. Instead, keep it short and sweet. End the kiss before she does. Then, avoid kissing her again for a short while.

This helps build the anticipation for a longer, more passionate kiss in the future. She'll love you for allowing the romance to build slowly.

Don't act aggressive or desperate

Since this is a discussion of how to make a 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.

If you want to kiss her, you shouldn’t immediately go for a make-out session without some sort of build-up. The key to easing into a kiss is to first sit really close to her if you’re sitting or stand as close as you can.

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 holding 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.

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! But don't worry because you're not alone.

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Make the first move on an older woman by simply taking the risk

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 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 thinking of what could have been.

Ask her out on a date

Older women tend to be far less forgiving when they spot this lack of self-assuredness.They have less time to waste on bumbling guys without the courage to go for what they want.

It won't be seen as polite and gentlemanly to not make a move at all. It will be seen as cowardly. Either that or she'll think you're not into her at all. Neither conclusion will have her jumping at the opportunity to see you again.

This isn't high school anymore. Most older women are looking for a confident go-getter who can look after them. You're nearly always better off making a move too quickly - and calibrating if she turns you down - than not making a move at all.

So, get over your fears and go for it!

Sure, there's more risk of an embarrassing rejection when you make your romantic intentions clear. In some cases, it might be smarter to be vaguer about why you want to swap contact details. Maybe, for example, she's surrounded by professional colleagues and would be embarrassed by an overtly romantic interaction.

Yet, for the most part, an older woman will appreciate the courage required to put your balls on the line in this way.

How to Make The First Move on a Date With an Older Woman

If you’re wondering how to make the first move on a date, don’t panic. Approaching older women and asking them on a date isn’t easy. Remember, she’s already on the date. That means you’ve done most of the hard work. She said yes when she could’ve said, “I think we’re better as friends.” That means she wants to get to know you better and see where this goes.

Older women don’t date just anyone. They’re much more selective than younger women because--like I mentioned--they have a much clearer idea of what they do and don’t want. You can put this down to years of experience, and being hurt in the past.

Always go for a cheek kiss, even if it’s the first time you meet each other. And when you do, pull her in softly by the waist for a brief moment. This is a great way to establish a warm precedent for your date. Let’s say the date is going well and you want to move in for a kiss.

Try and establish a physical connection before leaping to a kiss. That means holding her hand, giving her a hug, or maybe gently placing your hand on the small of her back if you’re walking side by side.

If she shies away from you, then back off. But if she leans into this kind of physical touch, then that’s a good sign that you can go a little further and lean in for the kiss.

Don’t be afraid to take the lead here. It might be the twenty-first century, but most women still expect men to make the first move.

Mistakes to Avoid when Making a Move on an Older Woman

Mistakes are nothing to be ashamed of. This is how we learn and grow as human beings. And we wouldn’t be able to appreciate success if we didn’t know what failure feels like.

So don’t beat yourself up if you say or do the wrong thing when it comes to anything in life. And that most certainly includes your love life.

That being said, there are some common mistakes you should know about, so you can avoid them when making a move on an older woman.

Don't be at a place where it's hard to be meeting or approaching older women

One of the biggest mistakes you can make when you make the first move on an older woman is being at the wrong place at the wrong time. There are plenty of spots where you can meet older women, but some are more hidden than others.

So if you're at a club full of younger women or at a bar full of other dudes, it might be time to switch it up. Find someplace that mature women are more likely to visit.

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Don’t make a move too soon

While it’s important you don’t take too much time, it’s equally important not to rush things. Being too eager can make you seem desperate and/or creepy.

So, how do you strike a balance between the two?

Trust your instincts and get a feel of the situation. Get to know her a little before rushing to ask her out. After all, you may find she’s not right for you and save yourself the energy. Once you’re on the date, take time to build up the connection and comfort between the two of you.

Don’t be upset if she “rejects” you the first time

You’ll probably view her giving you the cheek when you go in for the kiss as rejection. But it might not be.

Lots of women won’t kiss on a first date--even if they really like the person they’re with. So what you perceive as a “no,” might just be a “not yet.” Mention a second date and see if she is up for it. If she says yes, that’s a strong indicator she wants to get to know you better first.

Don’t wait for an older woman to make a move

This is a mistake the majority of men have made at some point in their lives. It’s true that older women will sometimes make a move on you. But you shouldn’t always expect it to happen. If you’re interested in her, then make it clear. You might just be missing the multitude of signs that she wants you to make a move!

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

Perhaps some of these tips might seem contradictory.

Nevertheless, it remains true that women--and older women especially--like men to be direct with their intentions. A man who is clear and shameless about going for what he wants is attractive.

At the same time, women appreciate a bit of subtlety when men make these moves. This allows them to maintain some sophistication and enjoy the slow progression of a blossoming romance.

To sum it up in one sentence: be direct with your intentions, yet subtle with your actions.

It might sound complicated, but you can master this with a bit of practice. When you do, older women will be melting at your feet.


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