How to Start Dating a Cougar: 15 Cougar Dating Tips

On the prowl for a cougar? 

I personally love the cougars. What I’ve learned over the years is that cougars are dying to date younger men – but that most younger men don’t know what they’re doing. 

“It’s not that I’m opposed to dating younger guys,” a cougar once told me. “It’s just that most of them haven’t got a CLUE what to do. It’s a major turn-off.” 

See, a lot of young guys assume that cougars would JUMP at the chance to date them because they’re young. 

It’s not that simple.

In this article, I’m going to uncover 15 cougar dating tips that will show you how it’s done. These tips are actionable and can be executed by anyone – it doesn’t matter what you look like or what your job is. If you execute, you could ensnare a cougar over the next few weeks, no problem.

15 Tips For Dating an Older Woman:

1. First, Decide Which Type Of Cougar You Want To Date 

Yep, there isn’t just one type of cougar. In my experience, there are actually two types:

  • Alpha cougars 
  • Beta cougars 

Your average alpha cougar is a sophisticated, classy woman who’s pretty damn street-smart. She’s intelligent, witty, ambitious, has a good career, and doesn’t need a man. Think Sex and the City vibes. She’s very aware of her sexuality, can be dominant if she sees you’re a beta male, and won’t settle for second best. She’s also super confident and cheesy chat-up lines won’t work on her.

Most young guys will find her intimidating, but there’ll be some who see her as a challenge. Experienced alpha males, on the other hand, will already be on her level and will know how to give her exactly what she wants. 

A beta cougar is quite the opposite. She’s feminine and aware of her femininity, but she’s not as independent or sexually empowered as the alpha cougar. She seeks emotional and physical validation from guys (especially young guys!) and wants you to make her feel better about herself. She’s aware of her advancing years and often see’s a young man as someone who she can use to impress her friends.

And while she’s not an alpha, a beta cougar is often looking for an alpha male who’s going to take charge and impress her with his confidence and his virility. 

Now that you know which type of cougar you’re looking for, it’s time to …

2. Understand That You Will Need To Do Some Chasing 

Can you imagine a 50-year-old lawyer chasing a 21-year-old student? 

Buddy, it doesn’t work like that. 

Cougars are experienced. They’re mature and they have a lot of self-respect. 

They have so much self-respect that they are done chasing. 

In other words, the chase is all down to you.

For some guys, this will be nothing new. They’re at the peak of their powers and, for them, the chase is part of the thrill. In fact, it’s often better than the catch.

For others, this is a concept they’ll need to get used to. Because let me make this clear: A cougar isn’t going to come chasing you when you don’t text for 3-4 days. You might want them to, but they’re not going to waste their time. 

“I want a man to put the effort in,” a cougar told me after we’d dated. “That’s what I liked about you. I had a few other guys lined up but I ditched them when I could see you’d made the effort.” 

Cougars like to be chased but they have no intention of chasing anyone. They’ve often got busy, fulfilling lives – heck, some of them even have kids! If you don’t text back for a few days it’s NOT going to ruin them. 

3. Don’t Mess Cougars Around 

Be honest: How many times have you arranged a date with a girl in the past … only to cancel or rearrange it because something better came up? 

“Hey! I’m really sorry to have to do this but I’ve gotta work late tomorrow. Can we rearrange for some other time?”

Maybe you’ve grown used to doing this because girls are always so eager to see you that they’re happy to rearrange:

“Sure! When’s good for you?”

Cougars, however, are different and you have to treat them differently. They’re the Rolls Royce of the dating world and you don’t keep them waiting.

If it turns out that you’re busy and can’t make the date, fine. But don’t expect them to give you a second chance.

However, if you’re getting stoned with friends instead, or if you’ve decided to make a date with someone “better,” there really is no coming back from that. If you’re serious about dating cougars, you better make them your priority. It doesn’t matter if it’s the first date, you need to show up on time and you mustn’t mess them around. They’re too experienced for that shit! They deserve better.

4. Make Her Feel Desirable 

One of the reasons a cougar might be attracted to a younger man in the first place is because she’s not getting enough attention from guys her age.

See, guys have this thing whereby the older they get, the less attention they pay to the woman in their life.

If an older woman is yearning to feel desirable again, be the one to make her feel desirable again. Don’t do what the other guys her age do – don’t be cynical and morose about life. Don’t ignore what makes her so sexy. Compliment her and make her feel good. 

5. Make Foreplay Online 

If you’re looking for a cougar online (and there are lots of milf dating sites you can use to find cougars, including Ashley Madison and Adult Friend Finder), it’s really important that you make foreplay with them. 


Because that’s what they want!

You could ask them for their favorite movie but that’s probably going to bore them. It’s certainly not going to excite them.

The best thing to do is to do foreplay as soon as you can. 

This means flirting with them via text and email, and asking them what they’re wearing. Cougars love that stuff because it makes them feel desirable. 

It also shows them that you’re not an inexperienced young punk who doesn’t know what he's doing. Cougars need to see that you know what you’re doing when it comes to the bedroom. If you don’t, you’re out before the first date. 

So, spend less time on the small talk and the “getting to know you,” chatter, and get straight to the good stuff as soon as you can. Be respectful but be playful. 

6. Save Them From Your Drama 

Just as you shouldn’t mess cougars around, you also shouldn’t subject them to your drama. 

What do I mean by this?

If there’s complicated stuff going on in your life that threatens to spill over into your dating life, it’s probably a good idea to save that for another relationship – or refrain from dating altogether.

See, while girls your own age might be drawn to your “mystery,” and while they might be keen (for whatever reason) to get involved with your personal dramas, cougars aren’t. They want you to be chill – because that’s why they’re here. Cougars are looking for young guys who are fuss-free, string-free, and drama-free.

7. Never EVER Mention Her Age 

I can’t repeat this one enough. Under NO circumstances you should EVER feel inclined to mention her age. As tempting as it may be to say something like, “the age gap really doesn’t bother me. Does it bother you? I know people might look at us and wonder what’s going on but screw ‘em!” you shouldn’t do it. 


Because it will make her feel self-conscious! Cougars don’t want such special treatment. She knows how old she is and she doesn’t need you to point it out to her. 

But you can … 

8. Mention Her Children (If She Has Any)

You might think that mentioning her children is another big “no-no” when it comes to dating cougars. 

But you’d be wrong. 

Let me explain … 

While a cougar really doesn’t need you to draw attention to her age, she absolutely won’t mind you mentioning her children because (usually) her children are her world. By taking an interest in her children, you’re taking an interest in her – and that’s super sexy. 

9. Don’t Talk About Money 

You might be under the impression that cougars are impressed by money. Unless you’re dating a sugar baby (which you are most definitely not, ha!), you should avoid money talk.

How come? 

Because while 19-year-old Stacey from college might be dazzled by your bank account and how much you sold last week, a cougar who’s been there, done that isn’t. She’s probably dated many rich men in the past, and maybe she has a great career herself. She doesn’t care if you’ve got a roll. If anything, boasting about money is a major turn-off for cougars. 

10. Be Confident 

While it’s true that you should exert confidence with WHOEVER you’re dating, it’s especially true when it comes to cougars. A cougar might be on the lookout for a younger, generally more inexperienced man, but she needs you to have supreme confidence. 

This means no fidgeting on your date. It means slowing your speech down, standing up straight, and taking the lead. Don’t let her pick a spot to sit at – you take charge and pick the spot. This isn’t arrogance, this is confidence – and it’s how she wants you to behave. Don’t dwell on the fact that you’re a lot younger than she is; take the reins and be a man! 

11. Give Her Space 

You should always give women space if you want to be successful when dating them, but cougars often live very independent lives and therefore need more time and space than younger women.

If she’s busy with her career, respect that. She’s had years to build up a network of friends and hobbies, and she’s not going to just suddenly give all of that up because you’ve worked into her life. 

12. Call Her

While you do need to give her some space, that’s not the same as ignoring her all week long. It also doesn’t mean that you should just text her and leave it at that. 

In order to make a cougar feel desirable, you should put in the effort to call her now and then, too. She’ll really appreciate it!

 13. Know Exactly What You Want 

Kinda following on from everything I’ve talked about so far, you absolutely must know exactly what you want when dating a cougar. 

When you’re younger and dating people the same age as you, it’s fine for both of you to be a bit confused about what you want. As you get older, though, that sort of thing won’t cut it anymore. People don’t want their time wasted. If you don’t know what you want to get out of dating a cougar, it’s probably best that you don’t bother at all. 

14. Be Classy 

In other words, don’t be late for a date, and don’t do the sort of things your buddies think are hilarious. For example, don’t make her “wait a minute,” until the game’s finished, and don’t even think about turning up to hers without showering. Like, don’t ever say, “Hey, I was running late from the gym. Mind if I shower at yours? It’ll save us so much time.” 

Always meet her high expectations. Dress well, smell nice, be polite, and be courteous. Show some class, respect, and sophistication. 

15. Get Her To Invest In YOU

Lastly, if you want to make it last with a cougar, at some point you’ll need to get her to invest in you.

This means introducing her to your world and showing her what makes you tick. She might not be used to younger males, so you’ll need to gently involve her in your everyday life. While this doesn’t mean you should take her to watch a game with the boys or go see your buddy’s on campus, it does mean you should involve her with some of your passions. Otherwise, she’ll just think you’re a tad ashamed of dating an older woman. 

Now that you know how to attract and date a cougar, the next step is to go out there and meet one. You can use dating sites like Match, OkCupid, and even Adult Friend Finder. Just make sure that when you go on your dates and execute these tips in this article. Before you know it, the cougars will be wild with desire for you. 

About Will Titterington

Will is a writer, coach and life lover who enjoys helping people reach their potential. Will has plenty of experience with Online Dating. He loves to test different apps and sites and share his experience on DatingXP. He loves art, sports, connecting with new people from all over the world, and making people laugh.