WhyDid Wisdom: Place Your Bets

By |April 19th, 2012|Why Did You Date Him?, WhyDid Wisdom|

james bond casinoI read a quote the other day that said, “The most common way to fail is by playing it safe. ”  It sounds a bit contradictory at first, but may hold more truth than you’d initially think.

After a breakup, or failed experience, you are likely to be barraged with comments like “take what you learned from this and apply it in the future” or “this is only going to make you smarter.”  You probably just want to tell these well wishers to GFY.  Well, as it turns out, as long as your eyes, mind, and heart are open, there actually can be quite a bit to take away from even the most terrible of situations.

After a very traumatic breakup with the Don Draper of Wall Street (or least in his head), I felt wounded and fragile.  (You guys remember that one?)  He was a bit of a wild card and I knew what I was getting myself into from the very beginning, but I was suffering from ITIS (I Think I’m Special) syndrome and took a chance.  When my hand played out precisely the way one might expect I was not totally shocked.  To say I was upset?  Yes.  Hurt?  For sure.  Surprised?  Not particularly.

I sat out a few hands to recollect myself, but the next time I stepped up to the table to play a little love roulette, I opted to place a much safer bet.  When I took a gamble on the other end of the spectrum (a safe bet) and lost again, it was most certainly a shock.  Probably more shocking and upsetting than losing a big bet.  How could I have been so careful, had such good odds and still lost?  I thought by aiming “low” or being conservative I might not hit the jackpot, but at least was going to win a lil somethin’.  I’d hoped for the best, took a gamble, and lost.

What I learned from both of these experiences is that it doesn’t matter if he’s the shiny, suave Wall Street type or the disheveled, artsy IT guy.  The big bet or the little gamble.  Anyone can hurt you or turn out to be a “loss.”  Having had bad experiences at both levels has made me tentative about making any decisions at all.  I tend to just sit and worry until the decision is eventually just made for me.  Well, that’s really no way to live.  There’s no way you will end up becoming a high roller just keeping your cards close to your chest.  Sometimes you have to just double down and put it all out on the table.

Just remember, a safe bet may be the most dangerous bet you can make.



Markets May Be Down, But Your Stock Could Be Going Up

By |April 7th, 2009|Somethin for the fellas, Uncategorized, Why Did You Date Him?|


So, one of my young male friends often talks about how he can not capture the heart of a worthy woman in this city.  He’s no schlub, mind you, but he hasn’t quite hit his stride in his career either.  He’s also on the younger side (read: under 30) and hasn’t quite gotten all of his partying/oat sewing out just yet.

He tends to meet lots of floozies and spends his nights with drunken sorority girls and women of low caliber.  Then the next day he wakes up (usually with one of those drunken floozies) feeling empty and most likely hungover.  I scold him about these little raunchy escapades, but to no avail.  I remind him that he is probably not hanging out in places that the respectable and date worthy women frequent.

Then I read this articleby the lovely and hilarious DABA girls.  It gave me an idea.  Maybe my dear young friend should be aiming much, much higher.  If these “take home to mama” kind of girls are feeling undersexed and under-appreciated by their banker/laid off banker bf’s, maybe there is a shot for a guy like him.  He may not be bank rolling like the guys of Wall Street, but he is charming, respectful, good looking, and I’m sure has plenty of “loving” to go around.  No disrespect, DABA girls, this might just be something fun to hold you over until the next boom on Wall Street… kind of like a disco nap before a big night out or a black and white cookie before your 10:30 dinner reservation at Waverly.  See? Everybody wins! Just a thought…