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10 Mistakes You Make When Making the First Move on a Cougar

making the first move on a cougar like this can be nerve wracking

Making the first move on a cougar show a level of boldness.

Not only do we encourage such a daring approach, but so do older women.

It’s well known that women find a confident man attractive.

For this reason, it’s not uncommon for women to reward bold behavior in men.

Older women especially appreciate a man that isn’t afraid and is willing to act.

That being said, there are still a few things you should keep in mind when approaching or making a move on an older woman.

Mistakes When Making the First Move on a Cougar

Let’s talk about the 10 biggest mistakes men make when making the first move on a cougar.

These mistakes are extremely common with men both in their day-to-day interactions with women or if they met via an online dating site catering toward older women interested in dating younger men (check out our rankings and reviews of the best sites for meeting older ladies to find out more). You can also check out our handy guide for creating a Match.com profile to meet cougars.


1 – Mistaking friendship for attraction

In this list we’ll go over ten different mistakes made in a variety of situations, whether it be before asking a woman out, or when you’re on a date with an older woman. First on the list, and this is a common error, is mistaking friendship or a co-working relationship for attraction.

It's important to note that which of the many great places to meet single cougars you met is crucial. Some places are much more conducive to creating romantic relationships (bars and clubs) instead of a professional relationship (at work).

Before asking a woman out, you should be quite sure that there’s a mutual attraction between you. This is the best way to avoid particularly awkward moments later on.

The Apps Dating Coaches Recommend Most To Meet Cougars

More and more older women are only using apps and sites to meet guys, especially younger guys. You need to be on at least one or two apps now if you want to get the best results you can. These are the apps that give normal guys the best success meeting cougars:

SiteOur ExperienceOur RatingFree Trial Link
Best Hookup Site Cougars
Experience Highlights
Experience Highlights
  • The best way to meet cougars for hookups by far
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
Try AFF For Free
Best For Relationships
Experience Highlights
Experience Highlights
  • Easily the best option for long-term relationships
  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
Try eHarmony
2nd Best For Hookups
Experience Highlights
Experience Highlights
  • 2nd best option to find hookups
  • Attracts an older crowd than most hookup apps
  • Pretty popular
  • Great free trial
Try Passion

2 – Texting her too much

Let’s say that you got an attractive cougar’s number, and you’re planning to ask her out on a date. Feel free to continue your conversation where you left off. But don’t get stuck in the vicious cycle of endless text messaging.

With texting, always keep it short and sweet. Make your move and see her again in person. This is one of the best tips you can find on the best books for dating cougars. So be little more low-key with your approach and she'll appreciate it.

3 – Talking too much

Let’s say you’re on a date with an older woman.

Unless she’s excessively shy, she will most likely enjoy talking a lot.

Don’t interrupt her when she does this.

Women love good listeners, which essentially means that you have to let her lead the conversation when she wants to, and take the lead yourself when she doesn’t.

It can be tempting to talk about yourself on a date.

But if you do it too much, it could ruin your chances of successfully making a move on her later on.

4 – Hoping that she makes a move first

What makes a cougar a cougar? For the most part, cougars are women who prefer to date younger men. And since they have more experience, they tend to be more direct. But that doesn't always mean they make the first move.

If you’re the type of guy that loves it when women make the first move, you’re not alone.

Many guys appreciate it when they can take a break from doing it all the time.

Not to mention that it’s exciting when you learn that a woman you like knows how to take charge.

But if you’re hoping that the woman you’re out with will be the one to make the first move, you’ll likely be disappointed.

It will rarely (if ever) happen, so always be ready to pull the trigger yourself.

With that said, it’s an incredibly special moment when the woman makes the first move.

5 – Being too passive

There comes a time on many dates where you’ll have a great opportunity to make your move. Especially after a few drinks or when there’s tension between you.

If you find that she’s suddenly talking less while making more eye contact, and potentially touching you more as well, it’s almost always the perfect opportunity to move in for a kiss.

But if you miss a great chance to make your move, you risk reducing the tension you’ve created. There is definitely a cost to being too passive. Pick the right moment, and don’t hesitate.

This applies to online dating as well. When you create your online dating profile to meet cougars, be as direct as possible. This is much more appealing than being wishy-washy about your intentions.

6 – Coming on too strong

Even though making the first move on a cougar is simple in theory, it can still be confusing sometimes. While being too passive is a mistake, so is coming on too strong. So if you're at a place where you want to be seduced by a cougar, avoid the temptation to make a bold move as soon as she says hello.

For instance, if you touch her too much before you allow her to get used to it, you risk ruining the date.

If you try to go for the kiss too early or in a crowded area before she’s comfortable with you, you’ll be coming on too strong.

You should find a balance that works for you, based on the situations you’re in and the women you’re with.

7 – Being too persistent

Without persistence, you would be unlikely to get anywhere on your dates, not to mention with women in general.

But being too persistent is a risky game.

You don’t want her to think you’re desperate, even if it’s unwarranted.

To avoid giving her this impression, learn to relax your approach, whether it’s for a kiss or to get her out on a first date.

Sometimes it pays to be nonchalant and indifferent.

A perfect example is when making the first move on a cougar.

8 – Being too aggressive

Similar to persistence, too much aggressiveness could ruin the vibe you’ve worked so hard to create.

Let’s say the date is going well.

If you go for a kiss, don’t begin to make out right away.

Keep the first few kisses short, and always leave her wanting more.

When done right, this also increases her attraction for you.

When you kiss too intensely right away, you may extinguish the tension or get ahead of yourself before the time is right.

9 – Moving too quickly

To expand on our last point, you should calibrate how fast you move forward. As a rule of thumb, two steps forward, one step back is a great way to proceed. When you're out looking for cougars, it might be tempting to zero in and immediately make a move.  

But when you try to move on too quickly, your date may come to an end abruptly.

For instance, if you’re at a bar with an older woman, don’t try to rush things after going for the kiss.

First kiss, to make out, to inviting her to your place is definitely an example of rushing the process.

Take your time.

It’s better to kiss her (leave her wanting more), order another drink, and leave the make out for later on in the night.

10 – Having an agenda

Lastly, another mistake when making the first move on a cougar is having an agenda.

While it’s inevitable that you have the intention to make a move, don’t try to structure it or plan it too much.

Otherwise, if things don’t go as planned, you may stumble when it comes time to make your move.

Let’s say you’re planning to kiss her during the walk after your meal.

She might suddenly realize that it’s really late, and as she rushes to get back to her car, you struggle to find a moment to kiss her when it wouldn’t feel forced.

This is merely an example, but the principle is one you should keep in mind whenever you’re out with an older woman.

Intentions are okay, but rigid plans are not.

Be flexible with your plans at all times.


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