Cagey as the Proverbial

Recently as Chuck sat begrudgingly at his keyboard banging away at a report while performing the role of uber successful businessman, an email popped up from one of his protégés. It read:

Hey Chuck,

Hope you are well.

I’m about to finish up in my current job and our division director is in town. The scouting report is as follows: 

• Mid forties
• Cashed up
• Tight body
• Attractive
• Perma single
• A look about her
• Cagey as fuck! 

Do you think I should take a crack at her?

Yours truly

Walter

Obviously receiving an email like that is the equivalent of a swift right cross to the chin. Chuck lives for emails like that at work! In fact Chuck had to get up and get a skinny latte in order to process the situation and provide the right advice.

Right off the bat, Chuck thinks that it’s imperative to highlight the use of the expression “cagey”. Long before “Cougar” came into vogue and evenings such as “Tag a Cougar” became commonplace, good looking older women were referred to as cagey veterans (often shortened to cagey or cagies if they were in a pack). The expression was derived from sporting circles where older players whose skills may have diminished got by on guts and guile. Think about it, an older woman, her once gorgeous looks ravaged by time, still managing to stay in the game by using the tricks of the trade she’s picked up over time (both in the attraction and then most definitely in the bedroom). Kudos to Walt for busting out the cagey line!

If Walt wasn’t leaving his job, Chuck couldn’t endorse taking a run at the most senior person in his division. Way too much at risk if you take the shot and miss. If she gets offended your career is likely to be up shit creek without a paddle. If you give it a shot and manage to nail her it’s going to be awkward around her knowing that you’ve plugged her and she’s seen your wiener….unless of course you manage to keep tapping it in which case its awesome!

Unfortunately, senior people in organizations are often quite protective of their positions and salaries and generally avoid fucking subordinates. Ok, Chuck should amend that to say senior “women” in organizations are often quite protective / sensible. Senior male managers don’t seem to have an issue nailing any piece of junior fluff that they can entice to a hotel (and then expense the bill).

There are likely a number of youngsters out there who wish a good looking, highly successful woman would take them under their wing and bring them into their manhood (while also picking up the bill for dinner and buying Playstation 3 games for them). Unfortunately that doesn’t happen that often and is even rarer in the workplace where most senior women have earned their position and wouldn’t blow it all on some tacker who pops wood when Target has a sale on underwear (ok, so for some women who’ve experienced erectile dysfunction at its finest, perhaps a stiff one is worth the risk).

However, since Walter is leaving Chuck has to say, “go forward young soldier”!

Hang on. (Chuck told you he had to ponder this situation over a latte)

The only thing Walter needs to consider is whether or not this woman can have any influence on his career moving forward. If he works in a fairly niche industry where this woman is a big swinging dick and can easily black mark his name through her contacts then perhaps it’s not so wise to have a dip at her. The last thing you want is to have a jilted lover subtly or not so subtly shitcanning your name all over your chosen industry.

Right, so if you’re leaving and you don’t work in an industry where this woman could ruin you, then Chuck says give it a red-hot go son! How many times in your life can you say you took down the most senior person on your division?

Perhaps the bigger question in this situation however is, “how are you going to pull this off?” It’s not like you can tap on her office door and suggest a quick goodbye shag on her desk instead of a card and a gift voucher.

Chuck would like to think that you’ve received some sort of vibe from her over the time that you’ve known her. Bosses typically hold their employees in 3 types of regard: 

• Fondness
• Disdain
• Apathy 

* Lust can sometimes enter into the equation, but tends to be more applicable to 45-50 year old men and their new 23 year old 6 foot PA who failed her typing test but has a winning personality.

If your boss displays apathy towards you then you have no chance whatsoever. Apathy is commonly displayed by management in the form of having to remind themselves to say hello to you if they bump into you in the elevator.

Disdain is fairly obvious since you’re likely to receive every crap task, never get any credit and be frequently passed over at promotion time. However, if you’re really good looking, sometimes you can parlay this disdain into a hate fuck since your boss may actually be jealous of your looks or secretly in love with you. In most instances however they don’t like you and you have no shot at penetrating them.

You’ll know that your boss is fond of you because they go out of their way to push you along, make small talk and grant you time off in lieu rather than making you take annual leave. There is a difference in fondness however. Yes, a boss can be fond of you and accept your home-made biscuits, but this does not mean that they would allow you to feed them the bone in the boardroom.

If you believe that your boss is fond of you and may be sexually attracted to you then it’s definitely worth the shot Walter. Chuck would recommend that you just get brazen and ask her out for a drink. You mentioned that she is in town (implying that she is normally from out of town) so she’s unlikely to have plans or commitments. You absolutely have to avoid going out in a group setting because it is unlikely that you can put any Gary groundwork into her in front of your colleagues, and there’s zero chance that she would succumb in front of familiar witnesses.

By simply surprise attacking her with the impromptu drink invite you are displaying confidence as well as sending a message. You’re telling her that you have an interest, there’s no hiding that fact. If she says yes, you’re a red hot chance. If she says no, you can rebound quickly simply by saying that you were planning on rounding up a few of the team but if she isn’t coming you won’t bother (then put on your sad face to really sell it). That will make her guilty and you could probably get another 20 bucks out of her on your going away present.

If you get a yes, you need to pick some place out of the way that your colleagues don’t attend (this will make her more comfortable) and have the willpower to not brag to co-workers who may end up cock blocking you by either showing up or talking about it around the office.

Right, so if she says yes and you get her into a bar for a drink, what then? Well Chuck’s not about to divulge all of his secrets but you will definitely need to ply her with a few drinks just to socially lubricate the situation and hope like hell that you can run a semi decent conversation. If you can put an hour to 2 hours of conversation in and things are going well (you’ll need to read the play here), then maintain your ballsy approach and suggest that you go back to her place. You want to do that for a number of reasons, 1) you probably still live with your folks and if not in a grotty share house, 2) she’ll be more comfortable in familiar surrounds, 3) you’ll have an excuse to leave.

While this sounds like a total long shot, Chuck is absolutely pulling for you on this one. It would be a story for the ages.  Just remember though, as athletes age they learn a range of nifty tricks to get themselves out of difficult spots – so make sure you pay attention if the cagey veteran goes for the squirrel grip!