Cougar Dating 101: 7 Must Know Tips for Dating Older Women

Cougar Dating Tips

Oct 27

So you finally broke the ice and found some mature beauty that rocks your world. It’s all over but the shouting (and tossing and turning), right?

Not so fast. Just because an older woman or “cougar”, as they call them in Hollywood, has given you a chance doesn’t mean you’re going to get an easy score. A lot of older women will actually give a younger guy a chance to impress them but then quickly lose interest once they discover that the young dude is immature, stupid or just an ass in general.

Avoid falling into the trap of becoming “like every other jackass” and instead rise to the top of the mountain, proving to her your worth, your unique personality, and yes, the body and mind she desperately wants. Here are 6 tips that will get you dating the cougar of your dreams…

Concentrate on being fun

Don’t hide from what attracts you to her and her to you – namely your youthful energy and enthusiasm. She can’t get that from older men who are her contemporaries. But she can get it from you, provided you don’t fall into the trap of playing it too safe, too stuffy or too much like dinner with your grandfather.

Your job is to make the date fun, spontaneous…yes, to make her feel young again. It’s okay to be enthusiastic, to be jokey and to be a little edgy as long as you don’t go over the top and read her all your dirty limericks on the first date.

Resist being a putz and talking too much about sex. That’ll come in time, naturally. For now, you need to make her feel something. Be fun and do something that stimulates your emotions and hers.

Avoid talking about “serious relationships”

Too many guys are so respectable, they’re downright avuncular when it comes to getting kinky. Right now, she doesn’t want to hear about your long-term family plan, your fatherhood potential or your views of commitment.

All she cares about now is feeling attraction – maintaining the same attraction that brought you both this far.

Don’t kill it by asking too many invasive questions. Instead, make her laugh, talk about the interesting things you’ve done, exciting experiences you have in common, or ambitions that are emotionally stimulating. The moment you start asking a list of questions, like it’s a job interview, is the moment you lose her.

Brag a little bit about your sexual potential…but don’t be crass

At some point, you’re both going to want to talk about sex. Don’t be shy…but don’t go full Howard Stern and scare her away either.

She’ll hint at the topic, you’ll take over.

Your goal now is to play up your heavy sexual desire (why she likes the idea of dating a young man to begin with) and to hint at your stamina. Women love long sessions of foreplay and anything “special” in the sexual arena is a great plus – BDSM kink, Tantra, Kama Sutra, anything kinky, so as long as it’s not too horrific. (Yeah don’t tell her the fantasy about the blindfold, clamps and the speculum…not on the first date, mmmkay?)

Now you also have to exercise some self-control and resist talking about your ex. Don’t mention that you’ve slept with hundreds of other people or that you like “older women” or milfs, or cougars in general. Any mention of the age difference tends to be a turn off, so just let go of that.

She wants to feel special, young, and beautiful. She also wants to think that you are only interested in exploring all these sexual fantasies with her, not just with any girl you can take home for the night.

Talk smart or make an effort to be smart

If you really want your cougar of a girlfriend to open her passions to you, you must come across as her intellectual equal. Older women may find dumb jocular young men vaguely attractive but they really go gaga over a guy who can talk to them about the greater things in life; literature, cinema, outdoors, philosophy, mysteries of the universe, and of course meaningful life experiences.

One common mistake jocks make is to try so hard to make her laugh, or tell her how sexy she is, and forget to actually pique her mind – stimulate her curiosity and tickle her emotions. She wants to feel as if she can have a great conversation with you in bed, after all that racket.

If you really feel out of your league in this respect then it’s about time you educate yourself so that you don’t have to fake anything. Read about history, about thrill sports, culture, a hobby…or think seriously about your own ambitions in life and get ready to wow her.

Be ambitious…and don’t be too modest

Too much modesty, when it comes to your future, won’t do you a lot of favors. Older women love to imagine that they’re dating a future superstar. That’s just human nature. It’s exciting to fantasize that you’re going to be the next Ashton Kutcher, or Justin Bieber or…Dustin Hoffman! (Actually he’s not too young anymore, Mrs. Robinson!)

So don’t sell yourself short. Talk about your ambitions, your dreams of accomplishment, and the rush you get from doing what it is you love. Don’t talk about the job you hate, or the things about life you despise. Let her see you “alive” and excited about your life. Bonus points if you can have her believing that tomorrow you’re going to be rich and famous – even if it’s just a fantasy.

Be honest

The thing is, you can fool a silly little girl with a BS story. An older woman, however, has been listening to men for years on end, and knows a lie when she hears it. She can also tell if you’re being duplicitous by hiding secrets or withholding information.

Once she figures out you’re lying or being dishonest, the relationship will start to crumble.

Even if your intent is just a one night stand you have nothing to gain by lying. Be open about what you want and don’t over-sell yourself only to reveal you’re blowing smoke later on. Older women respect honesty, but abhor dishonesty because it is the act of a coward. And cougars don’t have wild kingdom sex with cowards. They like lions, son!

Be persistent but creative

The truth is that most older women will test you, at least at first, to see if you’re serious about wanting to date someone older than you. She may mention the age difference as a test, to see how interested you really are. But that doesn’t mean you have to give up.

You do have the right to be persistent, but you do NOT have the right to be annoying, bullying or intimidating. Think of it this way: you only get a few chances to impress her. So if she refuses once, use your imagination to approach her again and ask her out in a more creative way or with good humor. Maybe she will laugh and give you a second chance.

Or she will let you know in certain terms that she is not interested and at that point it’s time to hang it up because you’ve just struck out. Persistence means being smart, not pushy.

Cougar dating is not as difficult as you think, but perhaps the best advice anyone can give you is to embrace yourself and accept yourself before attempting to impress a cougar. She wants you to be confident and in full control.

A man, not a boy, but with a very sexy age difference that gets you both a little hot under the collar. Show her what you got and have a great night!

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