A Step-by-Step Guide For Dating Up Older Women

I want to introduce you to a good friend of mine. His name is Dave Perrotta. He’s the founder of PostGradCasanova.com.

It’s a website for men who make things happen.

Dave knows his stuff when it comes to getting what you want in career, women, and life.

And today, Dave is doing a guest blog post for us.

A Step-by-Step Guide for Attracting Older Women

I’ve always liked women who can challenge me.

Women who have an edge – who know what they want, and go for it.

And of course, are sexy to boot.

More often than not, these types of women have been older than me. In some cases, ten or more years older.

When I was younger (18-21), I thought these types of women were out of my league. A lot of guys seem to feel the same way.

But in the last few years, I’ve come to see that these women are very attainable, even when you’re a young guy.

Age really is just a number.

But it wasn’t until I shifted my mindset – and altered some of my behaviors – that I started to attract more of these women than ever before…

And not just attract them and have a quick fling, but actually date them (if that’s what I wanted).


Well that’s what you’ll learn in this article.

If you’ve ever fantasized about attracting and dating sexy older women, you’re in the right place.

(Note: These same lessons can apply to more mature women who are your age or even younger)

But before we dive in, let’s touch on some of the reasons why you should try dating older women. 

(You’ll definitely be surprised by some of these).

Why You Should Date Older Women (The Hidden Benefits)

She’ll Challenge You 

Nobody is perfect – and odds are, you do a lot of dumb things around women. Things that you don’t even notice.

Like leaving the toilet seat up at her place…acting awkward about the dinner bill…letting out nervous laughter a little too often…

It’s the concept of “You don’t know what you don’t know.”

While many younger women will let your mishaps slide, older women will call you on your bullshit.

And you’ll be better off because of it.

You’ll Get Better at Sex 

Older women know what they want in bed, and they’re not afraid to tell you.

I once had a 30+ year old woman buy me a copy of “The Multi-Orgasmic Man” for my birthday. She enjoyed the sex we had, she just wanted me to last longer, breathe deeper, and be more in the moment.

Older women will give you the kind of constructive criticism you need to improve in the bedroom – things that younger women are too afraid to say, or not experienced enough to notice. This will give you a significantly better sex life.

She’s Better at Sex 

Many women hit their “sexual peak” in their early thirties – which basically means they want good sex – and a lot of it.

They also have years more experience, and understand how to please men – and also how to please themselves.

This all combines for a much better sexual experience for both of you.

You Can Learn from Her Experiences 

In your twenties, life can be pretty crazy. You experience a TON of changes, and half the time you don’t know what the hell is going on.

Older women have been through most of that already. They’ve seen that turmoil and (hopefully) overcame it and started to figure out who they truly are.

It’s awesome to have somebody around who’s “been there, done that”, and can discuss it with you intimately. Their advice can give you huge epiphanies and help you get to the next level in your life…

Or at that very least, add some depth to your personality and help you mature.

So, are you convinced yet? Okay  – now let’s talk about how to actually attract some sexy older women…

How to Attract Older Women

Get Comfortable Dating Girls Your Own Age 

It’s not that dating older women is more difficult… it’s just different.

And if you don’t have at least a little bit of experience dating women your own age, you’ll probably have a hard time.

So what does this mean?

You should get out there and follow advice like Tripp’s, and start meeting and hanging out with women in your age range or a few years younger.

Throughout this process, you’ll make mistakes and have some failures, and you’ll mature along the way. Plus, you’ll gain valuable reference experiences.

Why is this important?

With more interactions, comes more learning opportunities. You’ll understand how to deal with women in different situations. You’ll start to develop more empathy and confidence. You’ll see yourself as a man who can naturally start to attract women.

It’s the same reason why older women often tell me I seem older than I am – I have much more experience than most guys my age, and even more experience than guys older than me…

Because I was constantly interacting with women and taking action.

Go to Venues with Older Women

Now you actually have to go out and meet older women. The key is to go to venues where they like to hang out.

Hint: They probably aren’t getting drinks at the college bar down the street.

Do some research of the nightlife in your area. Start off by checking out some of the best lounges in your city. These are low-key social environments, and they’re often packed with attractive older women.

I’m from Boston, and one of the best locations there is Liberty Hotel. Try to find your best local location and start checking it out.

Also check out Meetup.com for some social and networking events. These are also great places to meet older women.

Approach Confidently 

So you’re at a place with some attractive older women. Now you need to go up and talk to them.

The key here is confidence.

If you approach them while thinking, “I hope she doesn’t notice how much younger I am. I hope she gives me a chance,” you’re going to get shut down.

Instead, see it as a casual conversation between a man and a woman. Don’t even let the age thing play a factor in your mind.

Make strong eye contact, speak from your chest, and approach with the same confidence as you would with a woman your own age.

Lead Unapologetically 

Leading is even more important with older women.


Well, when most younger men talk with older women, they make the mistake of letting the women call the shots.

It’s almost like they’re afraid to take the initiative just because she’s a few years older.

Even a lot of older guys make this same mistake. They just sort of hope that the woman will magically fall into their lap – that she’ll do all the work.

She won’t.

Whether you’re in a bar, setting up a date, or just hanging out with an older woman, you always need to be leading.

What does this mean?

In the bar, take her hand and lead her around. Figure out the logistics and confidently direct the interaction back to your place or hers.

When setting up a date, give her a potential day/time, the venue, and the activity.

For example:

You: “Hey Natalia – what’s your week look like?” 

Her: “Hey! Pretty busy, but free on Thursday night. What’s up?”

You: “Awesome. Let’s grab a drink at Liberty. 7:30pm sound good?”

Her: “Okay cool. That works! :)”

She’ll appreciate your initiative and might even compliment you on it.

Overcome the Age Difference 

As you get more experience attracting and dating older women, you won’t have to deal with the age difference as much – she’ll be able to tell you’re comfortable with it.

But at the beginning, you’ll notice that older women give you “age objections.”

Basically, they say stuff like, “You’re fun, but I think I’m too old for you. You should hang out with cool and attractive women who are your age.”

How can you handle this?

Instead of arguing, try to trigger her emotions. You can do this by clearly conveying your intent and/or being playful.

Here’s an example from a text conversation I had with an older woman:

Me: “What days off/free nights do you have this week to hang out with sexy/mean Boston guys?”

Her: “Look I really had fun on Saturday night! and yes, You are sexy/mean indeed but I think I’m too old for you and you should hang out with funny and cute younger girls.”

Me: “Age is just a number, I’m sure you’ve figured that out by now. We’re both mature adults here”

Her: “Age is just a number… yup, you are right”

Me: “As far as I’m concerned, you were the only girl worth talking to in that place. I thought you were sweet, gorgeous, and cool, and I was looking forward to seeing you again. I still am. So yeah, I think we’ll have a great time, and I think you know that too, and it’d be a shame to sacrifice it over something so trivial”

Her: “Ok… So you still want to meet up… I’m free tomorrow and Wednesday evenings.”

Me: “Wednesday evening it is then. I’ll pick you up and we can grab drinks in Providence. 730/8pm sound good?”

Her: “Sounds great”

Cutting through the bullshit and conveying your intent is powerful, because it shows your maturity. Most guys won’t do this, and it sets you apart.

Now, like I said, you can also beat the “age objection” by being playful.

For example:

Her: “How old are you?”

You: “How old do you think I am?”

Her: “Haha I’m bad at this. I don’t know. 25?”

You: “Maybe – how old are you?”

Her: “30.”

You: “Damn, girl. You’re way too old for me. This will never work.” 

If you choose this route, you need to make sure to actually smile and keep it playful. By jokingly disqualifying her based on age, you “flip the script” on her before she can say she’s too old for you.

It’s a verbal “push”.

Then, you can “pull” her back in by saying something like:

“It’s okay – I like you. Maybe I can make an exception.” 

And then give her a playful hug.

Even though you’re being playful, you give her a slight feeling that she’s lost you, and then got another chance with you.

Keep a Steady Head 

Don’t let yourself be overwhelmed by older women. This sounds obvious, but it’s a surprisingly easy trap to fall into. Especially if she makes more money than you, is further ahead in her career, and is more mature.

Remember that none of this is a big deal. It’s okay if you’re not a rich CEO. It’s okay if you still have some areas to mature.

Older women, and women in general, don’t care so much about where you are in life when you’re in your twenties…

They care more about the potential of where you could be.

And all that means is that you should be working to become the best version of yourself.

But there’s another place you can give value, too. And that’s by being a fun, adventurous guy to hang around with.

…The kind of guy who won’t judge her (like many older guys will).

How to Keep Them Around

Be Down for the Adventure 

Most times, you won’t end up dating an older woman long-term. Either she won’t want to, you won’t want to, or both. Because when you boil it down, if the age difference is large, the two of you will be at much different stages of life.

But that’s okay, and you can still have a ton of fun while it lasts. That’s why being “down for the adventure” is key.

You can experience new things together, do fun activities that you wouldn’t try otherwise, and be spontaneous.

Be Good at Sex 

This is another reason why it’s important to get comfortable dating women your own age. It’ll help you get better at sex.

Good sex will keep older women coming back to you – mostly because they know how rare good sex can actually be.

(Most guys don’t know what they’re doing.)

And it’s like a cycle, because the more sex you have with older women, the better you’ll get at sex (that is, if you’re open and willing to learn).

Get Your Lifestyle in Check 

Remember, in your twenties, your potential and trajectory is more important than your actual current status.

Women can go wild with your potential and trajectory. There are so many different things you can do and become. Hell, you could be a doctor, an entrepreneur, or a celebrity.

But if you already are those things, some of the excitement is gone. She can’t go wild with her imagination.
Basically, you want to do things to get your lifestyle in check and boosting your potential. That means figuring out what you’re passionate about and working on it, connecting with awesome people, and just doing fun and adventurous things.

Get in Shape 

A lot of older guys let themselves go physically. They stop working out and get fat and out of shape.

By working out and lifting weights, you can stand out to older women, and be more physically attractive. This is another thing that leads to better sex and keeps them around.

You know have a gameplan for attracting and dating older women. If you take action on this knowledge, I promise you’ll have interesting and awesome experiences with older women – and it might just change the trajectory of your life in the process.

Plus, you’ll have great sex. It’s a win-win for everybody.

  • Stefan Botha

    Hey Tripp, yesterday one of my ex’s actually considered to take me back but wanted some time to think. Then today she gives me the boot. I partially think its because i previous relationship didn’t go too well, but how do i fix it and get back together with her?

    • Hey Stefan. To get back with her, first you’ve got to give her and yourself, some space. Then go to work on improving yourself. After doing that for a while send her a casual text, saying “Hi”. If she responds positively, call her about possibly meeting up. If she agrees, show up looking your best and talk about the possibility of getting back together. Hope this helps for now and good luck.

  • Hassan Nasir

    hey tripp , i had a really great first date which lead to first base , how do i escalate her emotions even further and make her fall for me , and what do you suggest i do on a second date?

    • Keep doing whatever you’re doing because its obviously working. For a second date, something like the first, but more. For example, if you got coffee for the first one, then go to lunch together. Or if you had lunch for the first one, then go out for dinner.

  • Stefan Botha

    Hey Tripp. What can i do for a ex of mine that I’m trying to get back with, that she will find charming or attractive and actually consider taking me back?

    • Stop begging her to come back, give her some space, go to work on yourself, move slowly when contacting her, and show up as your best self. Good luck.

  • Toyin Mahmud

    whao tripp. you re so amazing in giving guys some of your powerful advice on how to seduce any woman. I am at my 20’s plus age and I bet ve been having difficulties going on a date with girls of my age but older woman re very easy to seduce when you ve confidence to approach them and talk with them but the only thing am not taking into consideration is going out to lounge where they hang out mostly but reading through your advice I think I will start to hunt for older woman at the point…lolz. thanks to you

    • That sounds like a great idea Toyin! Older women tend to be much more easy going and easier to talk to than younger ones. Good luck!

  • Irexa

    Tripp today at work a lady set me up on a date with her daughter- who is 2 years older. I’ve never met her, but I’ve seen pictures and she’s fiiinnneee. What should I say in the first text to spark interest and attraction?

    • “Hi.” then follow up with what is on your mind.

  • Dana Woodard

    “Howdy Tripp i really enjoyed reading this Article. it was a eye opener. this is my first time on here writing to you. what i’d like to know from you Tripp is how this apply’s to Online Dating. i’m 47. and i read a thing that was sent to me. and in part of the story it says you need to make a Woman feel safe, i am wondering how to go about that?” Dr. Wendy Walsh if you’ve heard of Her does a lot of Online Dating and said you need to make a Woman feel safe. Women need to know you’re not going to hurt them. they want to know that they’ll be safe, and feel comfortable in your presence. NO matter how good your game, you’re always one creepy move away from losing your chances with Her forever. that is why i don’t want to Blow it with these MUCH older Women. but as for as Online goes they also say you don’t want to have a Big age gap. say your age range is 22-50. they say you look like a creep to Women. on Match.com it shows the age range you have but on other sites like i’m on it does not. so i don’t know what she can see?” also it said you need to leave A Woman feeling little mystery in small doses. A woman needs to keep guessing. i’m wondering how you go about that?” i guess it’s NO different what the age is when you are having them guessing about yourself. when she get’s a little taste about who you are, but she can’t put all of the pieces of the puzzle together, i guess she kind of whips Herself into an attraction frenzy. when A Woman thinks about spending time with you, she will be much more likely to actually do it, The trick is you can’t actually tell Her to think about you. You’ve got to implant little pieces of bait in your profile and emails that she can pick up Herself. i’m just wondering how to go about that?” Another mindset that guys don’t think about. Women love, feeling like A real Woman… and you can’t make them feel that way by buying Her flowers and chocolate. Women feel feminine around someone who is masculine. the Women i like Tripp are 22- 67 i’m open to younger Women as well. i have A Woman who is 63. i seem to be able to Attracted, them. but it’s knowing what to do or say after that keeping them from losing interest. not every Women Online will be turned on by me doing that Online. but i get the sense they are turned on by what i write and say to them. i just don’t want to Blow this one. she’s very Attractive, and very High Caliber, looking. i love, Her fashion sense which is important to me. because when i search out Women Online the photos are very bad or grainy and Women Online including the age i mentioned 63. don’t hardly have anything written down making it hard to comment. some people look like they could be on the TV show “America’s Most Wanted” NO one makes themself I’ll prepared for this. they don’t have style or a fashion sense like this Women. i have very discern taste. she must be into me or why would she bother viewing me letting me know she’s noticed me?” i would “Just like a little Tripp Advice from you Thanks! for such a wonderful Article Sincerely Dana!

    • Tripp

      Hello Dana. Your comment isn’t on the main blog post for some reason. Maybe you deleted it? But if you post your question under the blog where we can see it, I’ll be happy to read it and give you my thoughts.

  • Dana Woodard

    “HI there Tripp i love, your article. when you said to say age is just a number does this work on any woman?” and how does this work for if your Online on a Dating site? i’m sure it’s different how you go about this. i was wondering if i should tell them age is just a number before they say what I’ve told you. i have a woman i’m pursuing that said something quite similar to what you said saying “HI you seem like a really a great guy you sound sweet and wonderful i don’t feel comfortable dating someone your age. were to far apart. you should date someone your own age. i’m sure you will have NO problem finding a great woman your own age. best of luck to you. i’m 47. she’s 63. i’m waiting for her to see and read my message and say what you said saying me: Age is just a number, I’m sure you’ve figured that out by know. we’re both mature adults here. me: AS far as I’m concerned, you were the only woman worth talking to on xyz, I thought you were sweet, gorgeous, and cool, and i was looking forward to meeting with you: so yeah, i think we’ll have a great time, and i think you know that too, and it would be a shame to sacrifice it over something so trivial is what i was going to tell her. what do you think about what she said. i look forward to your message Sincerely Dana!

    • It doesn’t sound like she’s interested. Oh well. Keep searching.