How to Date Cougars : Taking Cougars on a Date
How to Date Cougars : Taking Cougars on a Date

How to Date Cougars : Dates with cougars are far simpler to plan than dates with younger women.  They’re also far less expensive.  If I could sum up what your strategy should be in a couple words, it would be “drinks and booty.”

Logistics do play a factor in your chances of having sex with a cougar on your first date.  The more tight your attraction and game is, the more logistics don’t matter.  However, most of us (including myself) fall into the category where you need every edge you can get to close the deal.

The most important objective you have when on a date with a cougar is making sure she gets inside your house.  You should be on the bed with her making out at a bare minimum by the end of the date.

Because of this, it’s imperative that you have the cougar park at your place at the beginning of the date. I owe the essence of this to David DeAngelo, who pioneered this strategy.

Now how do you get a woman to park at your house or apartment?  There are two ways:

1. Plan a date at a spot within walking distance
2. Plan a date where you’ll be driving both of you there

If you have a bar or coffee shop within walking distance of your place, your dating will be a lot easier, no matter who you’re trying to hook up with.  The beauty of having her park at your place to go to a local bar is that it actually makes sense.  Even if you weren’t trying to get in her pants, it would make sense for you two to walk over together.

What makes this even better is that even if she insists at meeting at the bar, you’re only a short walk away from your place once you’ve had a few drinks and have gained her trust and affection.

The second option, where she drives to you and then you drive the two of you, is significantly more difficult.

For one thing, it doesn’t really make sense why she’d meet at your place instead of the bar itself.  If it’s a downtown bar and it’s very hard to find parking, then you can mention that as leverage, but it won’t be an easy, logical explanation.   Women generally like to have sex “just happen” and just “not notice” all

the clues that a hook-up is imminent.  This is why directly inviting a first date over for sex never works.
Even if they want it to happen, they can’t be part of the “planning process.”

Still, as long as you’re confident in your instructions to her, there’s a good shot of her complying.  Just know that if you meet her at a bar more than a few miles from your house, your chances of getting her back home are very low.  If she insists on meeting there and doesn’t want you to drive the two of you, then make it a nice half hour to forty-five minutes of conversation, and don’t try to take her home.

Instead, wait until next time you ask her out, and this second time, make SURE she meets you at your place.  If you let her convince you to “meet there” twice in a row, you have so much negative momentum built up that closing the deal becomes too much of a hassle to even bother with.  If she insists on meeting at the bar for the second date, just say no.  Let it be awkward as it ends.  Who cares?

Of course, if you have enough women in your phone at the time, you may even want to let go of a cougar who wants you to meet in the middle on a first date.  There is an abundance of women out there, especially older women, and she’s likely not special enough for you to make your life difficult just to hang out with her.

Some of your ease in getting her to meet at your place depends on how much time you’ve spent with her in person.  If you found her on a dating site and have had a single phone conversation, then she has numerous legitimate reasons to not meet at your house and get in your car.

If you met her at the bar and spent a good half hour or more with her altogether, then she’ll be more likely to feel comfortable getting into your car if that’s part of your plan.  Note that this is not likely to be true if you only talked with her for five minutes at a bar before getting her number.  A good IM chat and decently long phone call beats a quick bar intro and phone number grab any day.

You may have noticed I didn’t make meeting at her place an option.  The reason for this is that there are way too many factors out of your control.  She may have a nosy roommate, or even a child if she’s a single mom.  Also, you lose power in any environment that she’s more familiar with than you.  Even you looking for a step when walking up the porch or trying to find the bathroom signals to her subconscious that you’re in territory you don’t know and that she has the control of the situation.  The only exception I’d make for this is if she directly invites you to hang out at her place.  This is as close to an overt booty call as you’re likely to get, so in that situation, just let go of trying to direct where things are going.  Ride the wave instead and see what happens.

This is also why it’s essential you take her to a spot you know well for your date.  If you meet at a spot that she’s chosen, not only have you surrendered the decision-making power to her, but you’ve put yourself in a situation where you’re out of your element.  Your best case scenario is that she feels totally comfortable and safe, but has never been to the bar you’re at, so she has to take your lead.

Meeting Cougars on Date

When she shows up for the date, always hug her.  It doesn’t matter if you never even hugged her at the bar.  It doesn’t even matter if you’ve never met her before.  If this is your first time seeing each other face to face since chatting on the dating site, she might extend her hand for a handshake as a proper introduction.  Ignore this and go for the hug anyway.  DO NOT SHAKE HANDS WITH HER.  It doesn’t matter if it’s weird.  Trust me on this. Hug her even if it’s awkward and you feel that slightly resistant tension with your arms around her.  She may just relax into it.

If you kissed her at the bar, you may be able to kiss her right at the beginning of the date.  Older women are actually more likely to pucker up for a kiss right at the beginning of the date if you’ve kissed before. This is a great sign that your night will flow pretty easily.

How to Date Cougars : Date Plan with Cougars

As I said, your cougar dates will be simple and inexpensive.  Ideal is drinks at a bar.  Don’t take her to a loud bar.  If at all possible, schedule the date for a weeknight.  On Sundays through Thursdays, most bars will be a lot quieter.  However, most bars have a single night of the week where they have drink specials and the crowd and music is indistinguishable from a hot weekend night.  Do a little reconnaissance tomake sure that you’re not taking her to a bumping place.

Ideally, the bar is only 25% full or less, is fairly well lit, and is quiet enough to have good conversation in.A dive bar with seats is actually ideal for this.  Just make sure you don’t end up at a bar with standing room only.  Standing is awkward.

Pay for her drink, no matter what she orders.  There’s very little financial damage a cougar can do at a bar, if you take her to cheap enough place.  Ironically, the cheaper a place you take her to, the more likely she’ll be to put out. Remember that the older men she dates are further in their careers and can afford to blow a lot more money to impress a woman.  Because of this, cougars will have a side they show for these “relationship material” and “marriage material” guys, which involves them ordering fancy things off the menu.  You don’t want to fit into that mold.

In fact, a lot of your leverage comes from the fact that she’s in a younger man’s world.  A cougar doesn’t want to feel like an older woman getting with a young guy.  She wants to feel like a young woman getting with a young guy.

Many women, if not most women, had a time period of their life where they were a little more easy-going sexually.  Maybe they were outright promiscuous.  A woman doesn’t forget that part of her lifetime.  She actually misses it.  She may suppress it and say she’s “beyond that” now to her friends (or even to you), but she misses the time where she went to frat parties and hooked up with the star quarterback of the football team.

The best part is that you don’t have to look like that star quarterback to help her relive that.  90% of her fantasy is covered by you being a guy in his 20’s who’s looking at her like she’s a hot piece of ass at a frat party.

How to Date Cougars : Residual Age Issues on Cougars

If you’re catching my drift so far, you’ll understand that your age difference should not be mentioned at all during the date.  She is likely to not bring it up.  If she does, just ignore it.

There are a few issues where your age difference can be pointed out, and if this happens, things can get really awkward fast.  The worst of these is if you two go to a bar, and the bouncer asks for your ID but not hers.  You can circumvent this by saying “Hey, get your ID out,” when you get up to the bouncer.
That’s really your only intrusion from the outside world based on your age difference.  Everything else is within your control.

Remember that she’s trying to live the illusion that she’s your age, so you want to avoid any conversation pieces that could shatter that illusion.

One time I was going out with a woman who’d graduated from the same college I’d gone to.  Things got a little strange once it became clear that the gym, the food court, and my dormitory did not exist on campus when she went there.

This becomes common sense over time, as you learn to avoid conversations that point out the age issue.

The big three topics to avoid are:

1. Pop culture references (and when you experienced them)
2. Technology differences
3. Historical events

Pop culture references can be tricky because sharing 80’s nostalgia can be very powerful if you do it right.  It’s great to talk about how awesome Bon Jovi was in 1986.  However, if you follow up that with
“My parents played Living on a Prayer a lot when I was in the crib,” then things can get real uncomfortable fast.

You’re better off not mentioning any childhood experiences involving pop culture references.  Any talk about your childhood should be utterly devoid of pop culture context.  Don’t mention that you were in fourth grade when you bought your first Pearl Jam album.  Also avoid giving that wide-eyed look when she says she saw Nirvana in college when they were an unknown band.

The recent technology surge has made a lot of things tricky as well, especially for people in their early to mid 20’s today.  If you’re 21, you may have not have ever needed to open a Yellow Pages to find a local music store.  You may not have ever used a tape cassette player for music.

If you talk about using Facebook while in high school, you can very quickly make a cougar feel ancient.Be very conservative about these types of topics.

It’s the same for historical events.  Your conversation should be light enough that you aren’t talking about political elections or global tragedies anyway, so this shouldn’t be too much of an issue.

The rest of this chapter is assuming you’re either within walking distance of your house or that her car is parked at your place.  If this is just you two meeting for coffee or drinks at a neutral location, then just wrap your meeting with a hug and apply the following strategy for your second date.

Remember that a cougar is used to sitting at candle-light dinners with older men who might squeeze her hand at most (if they dare), with a table between them.  Maybe he’ll touch her arm when making a point and then quickly take his hand back.

You want to do the opposite and maul her like she’s a drunken sorority girl at your frat house.  This doesn’t mean you actually get her drunk, but you basically act like she is.

Here are some good examples of your physical escalation:

•?Put your arm around her waist and pull her in sideways, when you’re walking.
•?Pull her waist into yours when directly facing her.
•?If sitting down, periodically have your hands on her arms and body.  Let your hand creep up her arm.
•?Give her a shoulder rub and neck massage.
•?Let your fingers lightly link with hers, preferably under the table.  If it’s under the table, it feels like a sexy “discreet” secret between you that the rest of the world doesn’t know about.  It doesn’t matter if you’ve been overtly mauling her the rest of the time.
•?Lean your head against hers and smell her.
•?Lean your head into her neck and smell her.
•?At times, have your arms all over her.

Kiss her at the bar, whether or not you have before.  Even if it’s your first time meeting her, you should aim to kiss her in a public place if it’s at all possible. Chances are you won’t get a full makeout.  You actually might only get a little lip contact before she pulls back and says, “Wow, you are forward!” If she acknowledges that you’re all over her, just smile and shrug.  You don’t need to explain.  The fact that she’s still there is proof that she’s loving it.

Don’t keep mauling her non-stop.  Instead, lean back at times, and fluctuate between lightly touching her and going all over her.  Try not to completely lose touch contact, unless you sense her getting very uncomfortable.

How to Date Cougars : Moving Cougars Back Home : Move a Date with Cougars at home

At some point you need to get her back to your place.  The last thing you want to have happen is she looks at her watch and says, “Well, it’s getting late.”  If a cougar says this, it could very well mean that she has to get up early the next day.  It could also mean she’s not interested anymore, or that you haven’t escalated enough for her to be turned on and wanting more.  Or maybe you’ve just stayed at the bar too long.  Either way, your chances of getting her inside if she says something like this have just gotten significantly smaller.

It has to be your idea for you to leave.  You want to be taking the lead in every step of the seduction.

There are a number of ways to get a woman walking back towards your place.  With younger women, I’d suggest that you just say, “Let’s get out of here,” and when you get to your apartment, walk inside with her following.

However, with older women, you’re better off setting the plan for her to go inside before you leave the bar.  A pretext can be very helpful with this.

“I saved the funniest episode of The Office on my TiVo.  You have to check it out.”

You can also have a cool song to show her, or anything of interest.  Once she agrees that it’s a good idea for her to see it, you know you’re going to be able to get her inside when you walk in.

However, even better than that is if you can just say, “So, let’s go back to my place and hang out a bit.”She will often say, “Ok, sounds good,” without you needing to explain further.  Anything she agrees to without you giving an excuse or reason to do it will give you more leverage in closing the deal. She might say, “I don’t know…” or “Yeah I bet you want to hang out…” and seem to mull it over a little bit.

If this happens, it helps to make it clear that the expectations are rock bottom if she goes home with you.

“We’ll just relax, have a drink.  If you get bored, or it’s too late, you can just jet off.  No expectations.” She might test you on this a bit and say, “Really, no expectations at all?”

You have to stand firm on this, and give her the explicit and implicit right to not hook up with you, at all times.  She has to know that you won’t be angry or sad if she gets up and leaves without taking any clothes off. You can lie about this if you want, but it’s far more effective to legitimately be okay with her not hooking up with you.  The less attached to having sex with her you are, the better.

She may bring this up again while she’s walking with you to your place.  “Are you sure it’s okay if nothing happens?”  She may ask this again on your bed, even when she’s 99% sure she’s going to have sex with you.  Just give her the full permission no matter what.  The more inner space you give her, the more likely she will be to put out and this is How to Date Cougars.