Tuesday, September 29, 2009


*Ring* *Ring*

After just having lunch with Pencil Boy (which I bought myself), I figured it must be him calling to relay the sweet nothings he couldn't get off his mind.

"Yes darling?" I answered.
"Well hello there, aren't you in a happy mood" a raspy, over-confident voice responded.
"Ah, hello Jeffrey, I'm always happy to hear from you, how are you?"
"I'll be much better once I see you, what are your plans for Friday?"
It was Monday, he was calling a full 5 days in advance to be sure I would be his on Friday night. This was over-zealous behavior for Jeffrey. Appearing effortless was his game.

"Nothing so far, what did you have in mind darling?"
"Well.. partying like rock stars, what else?"
I laughed, "I'll see you Friday then" and hung up.

While I am interested in seeing him and slightly amused by his eagerness, binging the night away doesn't sound like the greatest time. I'll have to coax him into taking it easy. This much is certain though, whatever we do, it'll be a night to remember. Game on.

Sunday, September 20, 2009

Things I Miss

Hope you all enjoy the new trimmings, felt like I needed a bit of a face lift plus my archives work now :)

Earlier this year I decided to put the sugar lifestyle behind me. Feeling completely jaded after dating the Asshole of the Century (from now on referred to as AC). Peter, as in Peter Pan was my next foray into exclusivity. What a mistake that was.

For all the talk of abandoning the sugar lifestyle I really do miss it. I miss the all expenses paid vacations to exotic five star resorts. I miss the tuna tartar, jewelry for no reason and his visa with my name on it. Beer and fried food is not my idea of a good date.

Is it not possible to be a go-getter career woman and still be embraced by Chanel? My problem last time was garnering the motivation to achieve career success when all my material needs and wants were pacified. I think now my maturity and personal drive has solved that problem.

Towards the conclusion of my last hunt, I fine tuned a strategy for catching sugar daddies. It wasn't intricate, on the contrary, it reigned simplicity. I call it Über-fishing; throwing out as many hooks as possible and seeing what bites. I had an ad on all the Sugar Daddy sites, I was listed in multiple personals (local&national) and I attended as many upscale events as humanly possible. Draining but ultimately, it was craigslist that bit back. Go figure.

Now that I'm re-considering, I took a look at the popular Sugar Daddy sites once more. The mere thought of exchanging countless emails with misrepresented fakes, low ballers and ungracefully aging men gives me chills. Based on my previous experiences, I think much success (and peace of mind) is to be had by freestyling. This way you can completely eliminate the email tag and gauge his sugar-providing ability once his business card is in hand. You've just got to know where to look and show up in all your fab-ness.

I have a gift that benefits me quite well, I've mastered the art of active listening. During initial conversations I listen most carefully. This enables me to pick up hints as to what he desires most. Based on his history with other women and his own admissions I can become exactly what he wants. I can also read his non verbal cues and cater my every word and action to elicit a favorable response from him. This I do automatically now, with all men.

It's proven to be an invaluable skill. On the other hand, I'm unsure of the long term implications of this sort of manipulative behavior in the context of a healthy relationship. Wouldn't it mean I'm molding myself to another's image of the perfect lover rather than being myself? That I put my own needs second to his in order to get him to open his heart and his wallet? Food for thought I suppose... I think what I've missed most is sharing my thoughts with you all.

Wednesday, September 16, 2009

Cat and Mouse

So, friends... it has been a while. A little over a year to be exact and everything has changed.
I will be sure to play catch up but at this moment I have something to share. A new infatuation and possibly a new love. He's reckless, unpredictable, and so bad for me. We come from similar privileged backgrounds but my parents would never approve. Which is just as well because I've decided not to even think about children and marriage until after the age of 30. Ha! A far cry from the Tiff who just wanted to "get married or live comfortably with my rich boyfriend."

Though he is rich with a trust fund and full access to the family jet, much of that is irrelevant to me. There's a je ne sais quoi quality to him, we connect. He has a wild free spirit I can wholeheartedly relate to but I'm hesitant to get involved with him. I feel that "wild, reckless" phase of my life has long past. The phase during which I slept with strangers, partied all night and slept all day was fun but I'm not so much into that lifestyle now. This time in my life is about structure and developing the necessary skills to ensure my future success, such as discipline and punctuality. A part of me feels like he would only pull me back into unproductive habits that have taken years to overcome.

Jeffrey is 35 years of age, 6 feet tall and slight in stature. He is disarming (arrogant when inebriated) with a boyish smile, blond hair and hazel eyes. He has been bestowed with the tacky moniker of "Hugh Hefner junior," but... his attitude and presence is like a fucking magnet, I can't help being attracted. Is this wise? He has no idea I feel this way about him. I've gone out of my way to be that unattainable woman. Giving him shit everytime he leaves himself open and using my wit to taunt him. I've become such a challenge that I've unknowingly initiated an intense chase. It's cat and mouse, he wants what he wants. A man accustomed to everything falling into his lap always wants what is most unattainable. When we last spoke, he asked me "What are you looking for in a man?" To which I responded "What makes you think I'm looking?"

A truthful answer, which has provoked his curiosity, quickened his pace and leaves me in the involuntary position of the pursued... Shall I run or shall I succumb to him? If I'm to be his conquest perhaps he should be mine, wouldn't it be interesting if he fell in love with me along the way? After all, I can never turn down a good chase.