Cougar Bar Fun

Time: 2:20 a.m.  Place: a traditional hole in the wall-ish bar in Chicago.  The kind where you throw your peanuts on the floor.

The crew: I’m rolling with my work colleagues: GreatHairLawyer, LaidBackGinge, and DesignerGirl.

Our crew is in stark contrast to most of clientele, which seems to be pushing 35 on average. GreatHairLawyer and I are 27, D-girl is 22, Ginge is 23.

The ratios of P’s to V’s is at least 5-1 in this place.

The four of us enjoy ourselves for a while, doing some shots and chatting away.  Throwing the peanut shells on the floor.

15 minutes in, I notice a woman sitting at the bar blatantly staring at me.  Right at me. Her face is pretty; dirty blonde hair with darker, light carmel skin.  My favorite.   Alphas like me don’t break eye contact first.  She keeps staring, I keep staring.  The time becomes awkwardly long and she finally looks down and away.

She weirdly has her arm around the bald guy on the bar stool next to her.  Yet she just gave me the most blatant ‘fuck me’ eyes I’ve ever received.  I’m having a good time with my friends; I don’t speak with CarmelCougarface. We order more drinks.

CCFace gets up from her spot at the bar to go to the bathroom. I grab her arm as she passes me.

Me: “Hey.”

CCface: “Hey, I was going to talk to you right after I went to the bathroom.”

“Oh well I don’t want to stop you on your way.”

“No, it’s fine.  I’ll stay and chat now.  How old are you?”

“How old do you think I am?”


“No, you’re way off. I’m 16. Guess you shouldn’t be hitting on me that’s really creepy.”

“No really how old are you.”

“I’m 27.  You?”

“You are not 27.”

“Okay.  I’m not 27. How old are you?”

“Let me see your I.D. Or else I won’t believe you.”

“So how old are you?”

“How old do you think I am?”


(laughs, nods) “yea…so let me see your I.D.”

I give her my I.D.

Me “Now let me see your I.D…Okay, 1983.  I’m a good guesser.”

“I just can’t believe you’re 27…you look so young.”

“I’ve aged well what can I say.”

“So I’m in for a few days from San Francisco.  Do you want to hang out?”

“Yea maybe. Listen though, CCFace, I have to let you know.  I don’t know if you’ll be able to handle me.  A lot of girls can’t.

She doesn’t skip a beat.

“Okay little boy…listen, I don’t know if YOU will be able to handle ME.”

She insists on typing her number into my phone.  I oblige.  I have a girlfriend.  I’ll read the menu but I won’t eat off it.  She won’t be getting a call from me.

Not 1 minute after she leaves, a 35 year old woman approaches me and asks me if I am okay with the way CarmelGirl was hitting on me.  I say it’s fine—I like the older girls.  I tell her she is not looking bad herself—quite the cougar.

“Ohh, dooon’t use that word on me.  How old are you anyway?”

“I’m 20.”

I bought this 35 year-old lady a drink and we chatted about relationships and life for about 20 minutes.  I pretended I was 20 years old, she told me how she was at that bar with her (beta) ex boyfriend of 12 years.  I was in the zone.  No topic was off limits. Why don’t you want children?  How was the sex toward the end of that relationship?  What would a cougar do with a younger guy?

When all was said and done, she handed me her business card and told me I should call her to find out more about a sales position at her company.

At 3:30 a.m. on Thanksgiving morning.

How far we have come in gender dynamics.  These two women hit on ME. Cougar35 even pulled the old ‘was she treating you alright?  You looked uncomfortable in that conversation’ gambit that guys like to pull.

Men are meant to be the aggressor, but in a feminized world this dynamic reverses itself.  And the gender dynamic reverses for good looking males.  Just another reason to hit the gym and maximize your appearance.  And maybe you’ll get texts like these from women who approach you:


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