Dating Older Women? Here’s 7 Pitfalls To Be Aware Of

Cougar Dating Tips

Nov 29

Cougar dating isn’t all about life-changing experiences and mind-blowing sex. Sorry to break it to you, but dating older women comes with challenges that can wreck your chances if you aren’t prepared for them.

So in the interest of helping you navigate the waters of cougar dating successfully and skillfully, here’s a list of things you should know about dating older women!

Finer things in life

Slumming it is all good and dandy in your early twenties but there seems to come a time when your tastes start to…refine. By the time she hits 30, she’s going to appreciate classier, calmer environments than she did in her 20s.

And it’s likely that the older woman you’re dating is not going to think rubbing up against sweaty bodies in that overcrowded club you like is a fun way to spend a Saturday night. She’d much prefer to be be hanging out in a classy lounge, a jazz bar or listening to live music somewhere more low-key.

If that’s your scene also – brilliant, you’re going to get along famously. But if you’re still looking to brave the club scene every weekend…and expect your older lady to tag along, she’s going to drop you pretty quickly.

Scheduling matters

When you’re dating an older woman, keep in mind that she’s likely to have responsibilities that a 20-something doesn’t. If she has kids and is their sole caretaker, she’s going to need you to schedule ahead of time so she can set up babysitters.

If she’s a full-on career woman, her work might demand that you give her advance notice when you want to see her.

In your 20s, life isn’t so complicated – yet – and spontaneous meetings can be an everyday thing. But when you’re dating cougars, the ability to schedule dates in advance comes in handy.

She’s going to call you out

Women are born with a bullsh*t radar and they fine tune it over time. So by the time a woman is in her 30s and beyond, she’ll be able to sniff out bullsh*t before you even open your mouth. And she’ll give it to you straight – no beating around the bush.

So make sure you’re man enough to look her in the eye and be honest about things that make you squirm inside.

Think different to impress her

You might be able to impress a younger woman by taking her to a fancy restaurant but Ms. Cougar has already wined and dined in all the hot new spots in town. Oh, and she knows the wine list better than you ever will.

As for picking up the check, she’s able to cover it just as much as you can and she’s not particularly impressed by how much you’re making – even if it’s more than all your friends – since her income has most likely climbed up and above yours over the years.

So how do you impress a woman who already seems to have it all? Look outside the usual avenues you use to impress women.

In my experience, an older woman looks for thoughtfulness. She has her money, she has her life, she has the ability to do whatever she wants. What she wants from you is to know that you listen and you care – so give you attention and quality time. That’ll win her over a lot faster than wining and dining her at a trendy restaurant.

Age doesn’t always make you mature

Some newbie cubs make the mistake of assuming that just because a woman is older, she’s going to be more mature, more experienced, more understanding…pretty much, more of everything.

This is not true.

Many people grow better with age as life experiences shape them and challenge them and help them grow into better people. But some people never grow up. And this is as true of cougars as it is for all people.

Most cougars I’ve dated have been amazing human beings who openly admit that they’re a completely different person than they were 10 years or 20 years ago. They’ve evolved, they’ve matured and they’re a lot better for it.

But I’ve also met some older women who have been just as crazy and insecure as I imagine they were at 22. Not everyone chooses to better themselves so don’t assume a woman is wiser and more mature just ’cause she’s older – actually talk to her, suss her out and weed the immature ones out as quickly as you can.

Get ready for criticism

If both her and your friends and family are open-minded and accepting people, then thank your lucky stars. Otherwise, get ready to deal with judgmental people crawling out of the woodwork to reduce your relationship into stereotypes and caricatures.

The sad truth of it is that younger man older woman relationships aren’t as common as the reverse and you guys are pretty much the pioneers of cougar dating. And like all pioneers, you’re going to face some challenges. Make sure you’re up to the task.

She doesn’t see you in her future

This can be both a pro or a con – depending on where you stand on it. And of course, not all cougars are going to feel this way but many can. If there’s a big age difference between you, she just might not see a future with you.

Of course, there are benefits to this since every moment seems a lot more special and both of you will be fully in the present, determined to enjoy the relationship for however long it may last.

Leave a Comment:

Leave a Comment: