Meeting older women may be easy. You just have to be at the right place at the right time. But actually approaching them and striking up a conversation? That’s not as easy as it looks. So if you want to learn how to pick up an older woman, here’s the guide for you.
Take it from me. I’m an older woman who knows what works and what doesn’t. While not all mature women want the same thing, it’s safe to say that we all generally prefer certain approaches over others. No pickup “artistry” here because these tips are what really work on women.
Keep in mind that the advice below is generally for making a romantic connection. If you're only looking for something casual, you can check out our guide to finding older women who just want to hookup.
The Hookup Apps Dating Coaches Recommend Most To Meet Older Women
Whether you're looking for your first hookup or a long-term relationship there are a few apps that tend to give regular guys the best results. These are the ones that our dating coaches have seen guys consistently have the best results with older women:
| Site | Our Experience | Our Rating | Free Trial Link |
|---|---|---|---|
Best Hookup Site For Older Women  | Experience Highlights
| 9 | Try AFF For Free |
Best For Relationships  | Experience Highlights
| 9 | Try eHarmony |
2nd Best For Hookups  | Experience Highlights
| 8 | Try Passion |
Table of Contents
Where to Meet Older Women
A key part of knowing how to meet older women is being aware of where to meet them. Below, we have listed 10 hotspots for picking up older women. If you want more detail about how to pick up older women in these places, see our full guide on where to meet older women.
Upscale coffee shops
In most parts of the world, upscale coffee shops are hotspots for meeting older women. Whether they’re relaxing during the lunch break at work or after an afternoon’s shopping, you’ll usually find them here.
It’s not too difficult to strike up a conversation at this type of venue either. There are no distractions and they’re not going to be in a rush to go somewhere else. Approach respectfully, ask if you take a seat next to her, and you’ll essentially be on an instant date.
Online dating sites and apps
Online dating is taking over the world, and it’s not just Millenials and Gen-Z women who are using them. You can find a sexy older woman via online dating websites too!
There are certain online dating sites that are particularly fruitful for finding older single women too. Try eHarmony if you’re looking for a serious relationship, or Cougar Life and Adult Friend Finder if you’re only after a quick fling.
Either way, these apps help you to choose a suitable older woman from the comfort of your own home.
High-end grocery stores
A woman’s gotta eat! And you’ll find the sexiest single older women shopping for groceries at high-end grocery stores. You might not think of a high-end supermarket as a traditional place to meet your date, but that’s part of what can make it so magical.
Perhaps you start by making small talk about whatever you’re buying, then transition into flirting and asking her out on a date.
How to pick up older women in parks
On a warm summer’s day, the parks are full of people and you better believe that includes beautiful single older women. Again, this is one of the easier spots on this list because most people in the park aren’t likely to be rushing off somewhere else in too much of a hurry.
If neither of you are in a hurry, perhaps you can even whisk this woman off to a date at a nearby cafe or bar straight away.
Bars
You might not find as many older women at the local superclub, but there should be plenty at quieter wine bars or brasseries. Some of the women you’ll find here are actively looking, so try to keep your eyes open for signs that she’s looking for company.
Older women tend to enjoy a drink at the weekend just as much as their younger counterparts, even if they’re not raving on the dancefloor until 3 a.m. and beyond. And if they’re single, they’re usually going to be ready to mingle.
Yoga classes
Yoga classes are a good bet for picking up cougars who like to take care of their bodies. These tend to be more social than other fitness classes, so it won’t be too untoward to strike up a conversation before or after a class.
Restaurants with good bars
Older women tend to appreciate fine dining and can be partial to necking back a few drinks at the bar afterward. These types of bars are more appealing to older people than noisy bars with a DJ.
Classes and events
A lot of older women enjoy cooking classes. In fact, there are lots of classes and events that tend to attract older women. How about salsa classes or wine-tasting events for picking up hot, classy MILFs?
These types of events can be found on listings websites such as MeetUp! Or Eventbrite. Women enjoy meeting men when there’s something fun going on.
The great thing is: people going to events like this are usually doing so to meet new people. So, don’t hesitate to introduce yourself to a sexy older woman if you see one here. You already know that you have similar interests, so you can begin by striking up a conversation about this.
Gyms
Sure, there might not be too many older women waiting for the bench press, but perhaps you’ll find some making use of the yoga classes, pool or sauna. If you're a regular at the gym and there's a hot older woman who sees you a lot, you'll find it easier to pick up cougars at the gym!
Cruises or island vacations
These are the types of holidays that older women enjoy. So, if you want to meet an older woman letting her hair down on a vacation, you should be booking this sort of trip too.
How to Pick Up Older Women Successfully
Now you know where to meet women, so it’s time to put that knowledge to good use. When you head to one of the spots we’ve mentioned above, use the tips below to perfect the art of how to pick up older women.
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 picking up a MILF 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.
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.
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.
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 pick up 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.
Frequently Asked Questions About Picking Up Older Women, Cougars, and MILFs
How do you get an older woman attracted to you?
These are some of the best ways to pick up older women:
- Know when to approach them
- Be fun and playful
- How to pick up older women by asking her questions
- Get yourself online (we prefer eHarmony and AFF)
- Show her your mature side
- Be open and honest with her
- How to pick up older women by taking pride in your appearance
- Compliment her
- Take her somewhere she hasn’t been before
- Learning how to pick up older women is easier with confidence
- Say the right things
- Don’t be cheesy
How do you flirt with an older woman?
To flirt with an older woman, you should show her your mature side while also being fun and playful. You can also start by giving her a genuine compliment.
How do you pick up a girl that's older than you?
One of the best ways to pick up older women is by going online and using one of the top dating apps for older women such as AFF and eHarmony.
How can you date older women?
Dating an older woman is a balance of showing her your maturity while also ensuring you show her a good time that will remind her of her younger years.
