How to Message a Cougar Online: 6 Tips for Messages that Get Responses

Cougar Dating Tips

Dec 20

Ah, the art of how to message a cougar online can be a complicated one to learn. You’ve been social networking like a pro, have used every cougar dating site and filled the chat rooms with witty messages, yet you still can’t seem to create a vital link with that virtual personality that seems to pass you by like discarded clothing.

It can’t be your looks! I mean come on, you’re a hot young guy! Your profile photo was carefully selected to reveal your best qualities, and edited to disguise the not so appealing ones. It’s you – just without blemishes or unsightly wrinkles.

So what’s the deal?

Maybe your messages weren’t quite as witty or as clever as you thought, or maybe you jumped into deep waters when you thought you were taking a shallow swim. Let’s consider a few pointers on introductions.

Be Funny…But Be Real

Nothing attracts attention in a chat room like a flame war, especially one filled with sharp, witty comments. A quick wit is sure to bring you a fan base, but in the eyes of the one you’re trying to attract, you just might be a troll. The joker in online dating is like a clown who never removes his paint.

The audience loves the humor but knows very little about the person behind the mask – who is trying too hard to hide himself.

If you want to get through to that butterfly dancing on the edge of your society, laughing at your jokes, but never engaging in serious conversation, you’re going to have reveal a few honest aspects about yourself now and then.

For example, after saying something funny like…

“I can’t believe the romance computer matched us together. You’re so pretty, and physically speaking, I am simply beastly looking. I was once cast to play the Hunchback of Notre Dame in my school play, and we weren’t even doing The Hunchback of Notre Dame.”

(After a LOL)

“Seriously though, do you like the beard? I’ve been getting compliments on it and want to make sure people aren’t just humoring me. I need a really pretty face to offer an objective opinion.”

(After a positive opinion)

“Good. I actually decided to go for a new look about six months ago after I decided too many guys at work were coming in with little boy mustaches…”

As you can see, you’ve turned the “funny conversation” into an actual dating conversation. The next step is to ask about her fashion choices. A natural progression through topics, you see.

If your cougar of choice also happens to have a quick wit as well as some very outspoken opinions (which older women usually do), the worst thing you can do is hammer her opinions into the ground with some overboard comments! Who do you think you are, Donald Trump? Rush Limbaugh? Michael Moore or Kanye West? Do you really want to cast a negative mood over what should be a fun discussion?

So if you see that politics or religion or any other sensitive topic is an interest of hers, tread carefully. You don’t have to hide your real views, but don’t insist on getting the last word in and talking “too seriously” if all you’re doing is just trying to draw her out in conversation. Because the REAL point of topic is, you think she’s attractive! So control your political activism for just a moment, son!

For example:

“I see you’re into politics. What a coincidence because I’m running for president in 2020.”

(After a LOL)

“You know why you should vote for me? I’m an excellent winemaker. And I can make America Grape Again. Seriously though, total wine snob here. I prefer Pinot for very interesting reasons.”

Under-Estimated Humor

A ready wit can be a huge advantage as long as it’s not turned into a dueling sport. In the movies, the guy who ultimately gets the girl is the “funny guy”. He’s not always drop dead attractive. Sometimes what he lacks in physical prowess he makes up for in charm or in satirical commentary.

I saw a message on a social networking site recently and I found it quite amazing. It was a man who talked about hauling his desk sitting, middle aged spread into a bicycling marathon. He estimated he did far more pushing his bike than actually riding it, and groaned when he was passed by a man in his eighties, but his groans could hardly be distinguished from his locomotive puffs to catch his breath. He came in four hundred ninety-seven out of five hundred participants, but he was happy to say, he finished the race.

That’s a funny story and it would be a great way to use subtle humor and imagery to get an honest laugh – not to mention highlighting your athletic qualities and lack of pretentiousness. Honest humor that shows your ability to laugh at yourself places your person of interest at ease.

Nobody is really looking for a flawless person, only a compatible one. That the flabby bicycler actually finished the race added depth of character; a person who wasn’t concerned with winning, simply on not giving up on what he set out to do.

Add Spice to Your Message

Honesty may be the best policy, but for a girl to step into a relationship, she wants to feel she is being courted and not as though she was the best looking “cut in the meat market”. Read the clues in her profile that tells you her interests.

If she lists sports, learn the particulars. She may be referring to team sports, individual sports or she could just be a football fan. If she’s not a couch potato and is a genuine athlete, you really do need to go beyond idly musing how great it would be to join the community basketball team.

For example:

“I see you’re a Cubs fan! How about Dexter Fowler leaving?”

All that topic required was a quick Google News search, so you don’t even have to invest hours of research just to make sports small talk. Eventually, you will guide her into topics more your own speed…

Unless of course she IS a sports fan and in that case, you’ve hit the jackpot because what’s better than a cougar, a six pack of beers and Super Bowl 2017 followed by hours of celebratory sex?

Have Your Own Interests

Don’t try to shape your interests to fit hers. She’ll catch on if you’re too obviously bluffing about something you have no interest in. If her interests are in something you’ve never done but would like to try, let her know you’re ready to learn.

Older women are actually much more comfortable playing “mentor” when it comes to hobbies than younger women are. They don’t feel the instinctive need to “learn”…they already know. They want to teach.

For example, you’re up the creek without a paddle if she says she likes to go camping and you arrange a trip to the great outdoors without even knowing how to properly build a camp fire or pitch a tent! A better approach would be to say…

“I haven’t been camping much lately, but I do remember once going to Yellowstone National Park with my family…”

Or something related to the topic.

The Romantic Touch

A little humor gets the ball rolling, shared common interests create a bond. Sooner or later, the combination is going to create a magnetic pulse. If you’ve been paying attention to her profile, you’ll know by now her tastes in music, theater, art, and her favorite foods.

This is the time however, to read that common interest pulse. Few women can resist the lure of a four-star dining establishment, or the glamor of a weekend cruise, but these flings are generally reserved for the rich and famous.

If you want more than a single, spectacular date, scale down on your first date offers. Cater specifically to her claimed interest. If she’s a country-western fan, don’t take her to a jazz festival.

Instead, make your introduction part of your date pitch. For example:

“Cool! You love country music too? I was actually going to see Tim McGraw this summer…were you heading out to see anyone this season?”

Place a little adventure in your offer. Be imaginative. Maybe you know a little hide-away where the food is fantastic and the service exceptional or a hilltop view just right for a picnic – ideal for a woman who loves the outdoors.

Rivers and lakes can ignite romantic interest as easily as a beach side setting. Offer to take her on a canoe ride or on a river ferry complete with live entertainment.

Spare the Guilt Trip, Please

Girls don’t like phonies. They don’t like pretenders. They don’t like to be bullied for stating an opinion. Nor do they wish to feel guilt tripped into accepting a date. If none of your tactics have worked for getting her attention, forget playing on feelings of guilt.

She’s not going to have a higher opinion of you if you say things like, “Oh, yeah. I see what you’re doing. I’m not good enough for you, am I?” Chances are, her only reason for ignoring you is because she doesn’t believe the two of you are compatible.

If this occurs, it’s time to appraise your situation. Maybe you’ve been chasing the wrong girl. Maybe you’ve built a fantasy around her that just isn’t true in real life. While you’re being honest about yourself, be honest about appraising the comments she leaves.

You may be attracted to her sense of adventure, but never have been adventurous. You may love her devotion to small animals but can’t stand having a pet in your house. Your reality check begins with stripping away the fantasy and appraising the reality of accepting this person’s entire personality.

She’s not perfect and she knows her flaws. She is as anxious as you are as to whether or not you’ll accept them. She may have a good sense of humor, but she doesn’t want it to always be a battle of the wits.

Remember when in doubt, think simple.

As in:

“I see you like painting. Picasso or Monet?”

This is a general question, but you’ll notice it’s not overwhelming her with your intellect all at once. It’s better to take it slow, one question at a time rather than filling her screen with huge paragraphs.

Once the masks are removed, she wants an honest connection. Shared interests are important, but so are shared dreams. Your messages should be catered to her sensitivities while remaining truthful to who you are and what you believe.

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