How To Bag A Cougar Step 2

Men's Dating

How to Catch a Cougar: Step 2

Moxie Kline

Written by: Moxie Kline

Moxie Kline

Moxie Kline is just a lover. She has spent more than three decades exploring what it means to be a woman and to love and be loved by men. She writes about her adventures and discoveries at You can reach her at @MoxieKline or She wants to hear from you.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Unless you are fortunate enough to lure the mighty cougar into advancing on you solely by virtue of your adorable profile, it will be incumbent upon you to make the first move.

So we come to the all important first messages:

2. Laying the trap

Three principles should guide your early interactions with this fierce and majestic animal:

  1. Keep it classy.
  2. Keep it personal.
  3. Keep it real.

Remember this is a woman we are talking about. She is not a child. She is not a girl. She has reached a point of maturity that demands respectful treatment, so your communication must conform to a certain level of class.

Let me illustrate by example:

Keep it classy:



  • You are a beautiful woman.
  • You look so pretty and happy in the picture of you at Machu Picchu.
  • I loved looking at your pictures and they inspired me to write to you.
  • Your profile intrigued me.
  • I enjoyed reading your self-summary. You seem like a truly free spirit.
  • Hi, sexy. You’re hot.
  • Nice ______
    (insert body part of your preference here).
  • I was thinking I’d like to _______ you (insert sexual act here).
  • Ever been with a _______ guy?
    (insert descriptor of you here).
  • 😉

Now I am not saying the “not classy” approach will fail every time, but if you are really interested in a woman, better be safe than sorry, no?

If you don’t believe me, experiment. See what works for you.

Keep it personal:

As I mentioned in the first step, we women of the world do not like to think of ourselves as a type. We are all snowflakes, so approach us as the interesting and special individual we are.

Again, I illustrate:



  • I like what you say about _____ in your profile. I would love to hear more.
  • ANYTHING specific about her from her pictures or profile. For more ideas, see THIS.
  • I’m looking for an older* woman.
  • You are a MILF.**
  • Looking for a younger guy?

“Be yourself.

Do not pretend.”

A few additional caveats:

*Remember we don’t like to be reminded of our age. We also don’t exist for the fulfillment of your bucket list fantasies. Forgo references to age and experience and just talk to us like a normal human being.

**Please know your terms. If you don’t know what a MILF is, look it up. Using this word with a childless woman is a swift way to get yourself blocked. Remember we aren’t a type, so better to avoid categorizations like MILF and cougar all together.

Keep it real:

This is just the first commandment of online dating: Be yourself.

Do not pretend. It will never work, especially not with the wise and wily cougar. She will see through your pretense and it will immediately turn her off.

Are you of the more virginal variety seeking new experiences? Do you suspect that despite your relative youth, you are in fact more experienced than she is? Are you cocksure and self-confident? Or are you shy and more timid?

You are always free to pretend to be something you are not. Feel free to try it, but in my experience, such pretense does not lead to the most fulfilling in person interactions.

Your true nature will come out in the end, and no one likes to feel they have been misled. The best approach is to be open and honest and not attempt to put on airs.

This does not mean you should lay your agenda right out there on the table.

Please never send a first, second or third message that says any of the following:

  • “I am looking for someone to deflower me.”
  • “I want a teacher.”
  • “I want to be someone’s boy toy.”

Or any other reference to what it is you want. There is a time and place for intentions to be revealed and it is not in the early emails.

One final and very important tip:

This advice pertains to any woman, not just cougars. Always ask a question. If you start with a brief, classy opener and then ask a question we want to answer, it will be very hard for us not to respond.

If you just drop the compliment on us “You are a beautiful woman” (for example), then we have nowhere to go. At most you will get a “Thank you,” and then you are back to square one.

Invite us into a conversation. That begins with a question. As always, be sure to keep that question classy, personal and real.

Step three is next: closing in on your prey and converting your e-correspondence into a date.

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