How To Pick Up Older Women From A Woman Who Knows


How to pick up older women according to the experts

If you’re wondering how to pick up older women, you’re in the right place. Let me begin by letting you in on a little secret: older women aren’t all that different from younger women. There are certain things we look for in a partner in our teens that remain the same when we reach our thirties, forties, fifties and beyond.

That being said, there are a few things that change as women age. These reflect their behavior and tastes in dating and relationships. An older woman has a lot of experience under her belt and she is more likely to know what she wants (and what she doesn’t want). So she doesn’t want to deal with immature boys trying to pick her up.

Find out how to have the best chances of hitting it off with an older woman below. If you're only looking for something casual, you can check out our guide to finding older women who just want to hookup.

How to Pick Up Older Women Successfully

If you want to learn how to pick up older women, we’ll let you in on a few secrets. Here are our top 11 tips for how to stand out and impress an older woman you’re interested in.

Know when to approach them

Timing your approach when it comes to older women is extremely important. Many mature women don't appreciate being interrupted when they're out with friends or unwinding at a cafe. This is where being tactful and observant comes in handy.

When you spot an older woman that you like, try to get her attention subtly. Pass by her a few times or be in her line of sight when possible. Then try to check if she's also looking around for someone to talk to.

When you see some of the signs that she wants to be approached, that's when you can make your move. It beats having to approach her out of the blue and surprising her (and not in a good way!).

Be fun and playful

One of the main reasons an older woman chooses to date a younger man is because she’s attracted to the youthful, playful side of you that she can’t find in men her age. Older men may have been through the mills and usually have a more jaded outlook on life. You probably don’t.

So the first step to attracting them is knowing where to meet older women. to keep the mindset of a kid and just focus on the both of you having a good time.

Being younger, your energy levels and vibrancy should naturally be higher than most guys who flirt with her. Use this to your advantage and emphasize it. Always keep the focus on fun and positivity.

You can make it a lot easier on yourself by checking out the spots where finding single cougars near you is easiest. This is where older women are much more open to meeting single guys.

A great way to have fun is to make her laugh. Not many women can resist a man who can crack a joke, and this also helps to break the ice and relax her in the process.

You don’t have to try too hard or make a joke about everything. A few quick-witted and well-timed jokes are all you need. Keep a healthy balance between your playful side and being serious. This way she’ll know you’re not playing games and you have a level of maturity that makes you a serious match for her.

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How to pick up older women by asking her questions

Older women have a lot of life experience when it comes to, well, everything!

They’ve been on the planet longer than you have. So chances are they’ve seen and done some pretty interesting things and have wisdom, intelligence and strength to show for it. When you make the first move on an older woman, make it your priority to get to know them. So ask her plenty of questions and really listen to how she responds. Don’t interrupt her, but make sure to smile and maintain eye contact with her while she’s speaking.

Women (and men) love to feel heard and to feel like someone is genuinely interested in what they have to say. You never know where the conversation might lead to.

Get yourself online (we prefer eHarmony and AFF)

If you have only been looking for older women in the traditional spots, you’re missing out.

Older women are busy and really appreciate the efficiency of meeting a lot of people in a short amount of time. This is why online dating is a gold mine for meeting amazing older women. You can easily make a move on older women here because you know for sure that they're single and looking.

We have rated all the top sites to meet an older woman. Out of all the sites we tried, eHarmony and AFF have consistently been our top choices. There are a few reasons why:

AFF is the best option for hookups - We've tried over 100 different options to pick up older women for a hookup and AFF has blown them all away. We haven't seen another app work as consistently well for most guys yet. It's strickly for more physical relationships so if you actually want a relationship you should try elsewhere. Check out their free trial and see for yourself.

eHarmony is the best option for relationships - No other site or app compares to the success we've seen with eHarmony when it comes to real relationships. Their track record is simply amazing. nearly three out of ever 4 marriages that started online began on eHarmony. That's just crazy! No other site comes close. If you want a relationship you have to start with their trial offer here.

Show her your mature side

A cougar is comfortable and confident within herself. She is able to single-handedly navigate her life. It takes a great deal of independence, courage and discipline to do this, so naturally, these are the traits she desires in a man.

That means it’s your job to show her how mature and responsible you are. Help her solve a problem she’s going through right now. Share a personal story that demonstrates some of these winning traits. Show her you’re more than capable of caring for her even though she doesn’t need anybody to take care of her.

Be open and honest with her

One of the most attractive traits to any woman is someone who is honest and completely trustworthy.

Many men believe it’s okay to tell white lies now and then (or big ones 24/7) in an attempt to impress a woman and trick her into liking him. The trouble with this is you’ll always get found out eventually. So it’s much better just to be honest from the start, especially as this is endearing to women.

We encounter so many liars in our dating lives that stumbling upon a man who’s open and honest is a welcome breath of fresh air. Let your guard down and don’t be afraid to be vulnerable with her. Trust me when I say that women love a man who is real and genuine with them.

How to pick up older women by taking pride in your appearance

Older women know their bodies inside and out. This means they know exactly what to wear to flatter their best features. They’re elegant, sophisticated and classy. And this is reflected in how they present themselves--from their clothes to their hairstyles and makeup.

If it’s clear that she still looks after herself and her figure, then she’ll be looking for a man who does the same.

Keep yourself in shape by hitting the gym and being mindful of your diet and eating habits. Make an effort with your appearance. That means choosing smart-casual clothes that fit you well but also help you stand out from the sea of other men. If fashion isn’t your forte, enlist some help from a friend or an in-store stylist. Whatever you do, make sure your clothes are clean and not creased. A crumpled shirt will tell a cougar that you’re a mummy’s boy who can’t take care of himself.

Get a haircut, shower and shave (or at least trim your beard if that’s the look you’re going for). Older women love the sight of a well-groomed younger man because it helps them feel younger.

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Compliment her

Everyone loves a compliment. So if you want to understand how to pick up older women, you need to be able to give compliments with confidence. The best compliments are always ones that have thought behind them. Sure you can say “you look nice” or “I like your dress” and it won’t be received badly. But it is a line they are likely to have heard 100 times before.

If you really want to impress your older lady, then tell her why you think she is beautiful and interesting and funny. When you make a compliment look her directly in the eyes. Make sure she knows she has all your attention. There is nothing worse than a half-hearted compliment or one that is shyly mumbled when staring at your shoes.

Take her somewhere she hasn’t been before

A cougar has been there and done that. So if you want to learn how to ask an older woman out and keep her interested, put a little thought into your dates.

It is fine to play it safe at first. But as you get to know her and learn more about her and then try and come up with more imaginative dates. Or take her somewhere she has never been. Give her an experience that she has never had before--this is sure to go down well.

Learning how to pick up older women is easier with confidence

Confidence is hugely important when trying to pick up an older woman. Cougars tend not to like beating around the bush. They expect the younger guys to be sure of themselves, without slipping over into arrogance. They want you to approach them. So even if you are feeling a little nervous, don’t let it show.

Stand up tall and straight. Keep your head high and shoulders back. Offer lots of eye contact (not too much that she thinks you’re being creepy), smile at her and speak up.

Say the right things

If you are looking to make a move on an older woman, make sure you say the right things.

If you’re in a crowded bar, you could stand near her to try and hear what she’s talking about before approaching her. Then use that knowledge to strike up a meaningful conversation with her. Alternatively, simply ask her how her day was, what she’s thinking about right now or offer to buy her a drink.

Avoid inadvertently insulting her. Lines like, “wow you look so good for your age,” do not count as compliments. A better approach would be to compliment her on something non-physical, which will usually require you to have a conversation or two with her first.

Single woman

Don’t be cheesy

A cougar wants to be approached by a guy who has a bit about him and isn’t like every other guy. Cheesy pickup lines show that you’re not original and kind of immature. Don’t be that guy.

She has probably heard every line out there by now and is way past the point of being entertained by something that may have tickled her decades ago.

As we’ve mentioned already, funny is great, but cheesy gets a resounding no.

Pick up older women by being the man she’s looking for

Getting attention from a younger guy is empowering for older women, and this alone can make a woman feel confident and sexy. So remember that the simple gesture of you approaching her is probably already making her feel good. Be kind, genuine and charming and she’s sure to notice you. There are plenty of reasons to date an older woman, but being the right man for her can be the key to making her want to date you.

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