Boy Meets Woman

I have an admission to make on this public forum.  It’s a realization I’ve recently come to.  I am not consistent in meeting self-imposed blog deadlines.  When I created this website, a social-marketing-guru-friend (shout-out to HOOPLAH Inc – – thanks LH) suggested that I blog “regularly” at whatever interval I felt I could commit to.  In being realistic about my capacity and schedule, I “committed” to once a month…more specifically, on the 14th of each month.  As I post this on the 15th of February – one day late and following my January delinquency where I posted nothing – I am abandoning this monthly schedule and freeing myself of the undue pressure it’s been creating in my already hectic life.  From now on, you’ll just have to check back in here frequently (that is, if you’re remotely interested in reading this blog), or follow us on Twitter (@SittingIn_ATree) or on Facebook (Sitting In A Tree) so that you’re notified each time a new blog gets posted.  Regardless of how you stumbled upon this blog today, I’m glad you did and thank you for taking the time.

So, today I want to talk about cougars.  I was on a dating website yesterday afternoon – procrastinating writing this blog entry – in search of suitable mates for a few of my matchmaking clients.  It’s worth noting that I have my own, legitimate profile on said dating site, and that I’m a 36-year old woman.  Shortly after I logged in a 22-year old male requested an IM (instant message) chat with me.  I recognized his online name.  I don’t often get contacted by 22-year olds (I’m much more popular among the 50+ crowd).  I recognized his online name because we had just exchanged messages the week before. 

When he contacted me last week and I saw his age…after I threw up a little bit in my mouth…I quickly went to decline his invitation to chat and wanted to make him go away.  Something stopped me though.  I had just finished coaching a female client the evening before to be more open to talking with any and every man who crossed her path (the rationale for which could be the topic of another blog entry…e-mail me if you’re interested).  Less than 24 hours later it seemed hypocritical of me to go against my own advice.  So, I found myself clicking the “yes” button, inviting this young man onto my computer screen.  I expected him to say something within the first two sentences that would make me regret my decision and allow me to justify ending the chat, but that didn’t happen.  He was polite, engaging and full of flattery…but not too much where it seemed disingenuous or cheesy.  We chatted for about five minutes, he asked if he could add me to Facebook, I said “sure, why not?”, and that was that. 

Yesterday, after I again accepted his invitation to chat, he started with the typical “how was your weekend” banter.  He then asked “what have you been up to?” to which I replied “Enjoying life”, to which he replied “have any hot sex?”  BOOM!!! with the attitude as my little 6-year old friend Jory would say.  And there you have it friends and readers.  Online dating at its best (insert sarcasm).  I knew what he was hoping for (cyber sex, a real-life encounter – just in case this isn’t obvious), and maybe…just maybe…if I were ten years younger (read: naïve), I might’ve taken the bait (who doesn’t enjoy a bit of flattery?).  Being the evolved, liberated woman that I am though, I did respond with “I do not feel comfortable discussing my sex life with cyber friends”, to which he replied “fair enough”.  He did, however, continue to pursue and I had to give him credit for trying. 

My boundaries are, perhaps, broader than yours…but not to worry.  I know where to locate (and how to use) the “Block User” feature on all dating sites.  I have my Muay Thai boxing moves ready to go – especially the mean right elbow I’m told will slice a person’s face open.  I sleep with knives under my bed (KIDDING).  Anyway…point being…while my patience and willingness to engage a horny 22-year old may have far exceeded what is considered “required”, polite or normal, I do not feel that it came at any cost to me.  I asked him “have you not yet fulfilled your older woman fantasy?” to which he replied (without hesitation) “nope”.  OK…so now you’re certainly wondering why I would continue chatting with this young man and some of you may be thinking “cougar” but the truth is I like to help people and kinda felt sorry for the kid.  Here he is…in pursuit of a popular male fantasy and getting nowhere with me.  I wanted to both save him some time and give him some pointers.  So, I suggested that he not try so hard and that he be more forthcoming with the next woman he meets.  The truth is we – as “older women” – usually know what’s going on when a younger man approaches us…especially online.  I thought that it might serve the little “cub” well to just put his fantasy “out there” and be patient.  I was confident that in doing so, his mission would eventually be accomplished.  There are, after all, many women out there seeking “boy toys”…aren’t there?  Hence the topic of this blog – cougars.   

So…what is a cougar?  Does anyone agree on its definition?  I’m (obviously?) not talking about the predatory mammal from the family Felidae, native to the Americas but, rather, the term used – quite liberally in my opinion – to describe older women engaging in sexual activity with younger men. 

I’ve been called a cougar.  I’ve felt like a cougar (hence why I threw up a little bit in my mouth when my 22-year old friend first contacted me).  I’ve been accused of wanting to be a cougar.  I’ve been told I’m the furthest thing from a cougar.  Regardless of the circumstances, I’m never sure how to react.  Sometimes I think being called a cougar is a compliment and that I should take it as such.  Other times, I shudder at the thought.  My challenge is that I don’t know that I fully understand what it means and when I’ve endeavoured to find out (usually through my male network) my genuine curiousity has been misinterpreted as defensiveness and I’m told “don’t worry about it, you’re still hot”.  (Such nice friends I have.) 

According to Urban Dictionary ( there are over 100 definitions of “cougar”, of which these are just a few:

An older woman who frequents clubs in order to score with a much younger man. The cougar can be anyone from an overly surgically altered wind tunnel victim, to an absolute sad and bloated old horn-meister, to a real hottie or milf. Cougars are gaining in popularity — particularly the true hotties — as young men find not only a sexual high, but many times a chick with her shit together.

A woman in her sexual prime who prefers to hunt rather than be hunted. A cougar’s victims are usually under 25, as cougars prefer to mate with men who still have hair. Cougars generally feed and then continue hunting, as they enjoy role reversal.

Cougars are only usually interested in men under the age of twenty-five. Also, Cougars are non-committal, choosing to move from mate to mate without ever settling down. It is not uncommon for the same Cougar to attack (sleep with) many different men in the same group of friends. Furthermore, Cougars are older and more practiced in the ways of snaring a mate so they will rarely broadcast their intentions to sleep with you until you are already in her Jetta, headed for the condo she just bought. It is this elusive behavior that earns her the name “Cougar.”

Hot and sexy older woman, usually in her 40s or 50s, single or married, who is sick of her same-age counterparts which are usually hairless, have big guts, who only talk about their insurance premiums and have the TV remote control attached to their hands. Cougars are attractive, in their sexual prime, who know what they want and aren’t afraid to go after it. BIG misconception is that they dress cheap, wear hot pink nail polish, animal skin prints and are not-so-attractive old-looking hags with bleached hair (Yeah those women exist, but they are NOT cougars). True cougars are classy, beautiful creatures who have made their successes on their own, have real brains, usually with expensive cars/homes, and are real head turners. Cougars seek younger men, and don’t have to sneak up and attack…they know their younger mates are eager to get an experienced woman who won’t ask if they’ll call them the next day. Being a cougar is a positive thing.

I would love to hear from you on all matters “cougar’.  What do you think about cougars?  What do you think about relationships involving older women and younger men?  What have you experienced?  Tell me – here or by e-mailing  Until next time.

Inspiring a Love Movement …