By Haddon Libby

During the day, I manage investments for my friends and clients.  Despite 2016 being one of the roughest starts in history, my core stock portfolio is essentially flat…which is 5-7% above the market.  Not bad, right?  In fact, damn good.  I’m patting myself on the back.

When it comes to understanding women, I have been known to be equally adept and clueless – a curious mix that baffles my partners as well as myself.

I bring these things up as V-Day is upon us.  I am not referring to the date when the Allies defeated Nazi Germany but a more clear and present danger to modern men – Valentine’s Day.


Let’s face it, pleasing men is pretty easy: we want food, sex, money and our egos stroked.  If we can get all four at once – even better!

As for women…things are infinitely more complicated.

An overly practical person who understands that this time of year has the highest number of fatalities in the Coachella Valley might think about his and hers mortuary plots.  While this is the ultimate statement of forever together, it is more likely to be misconstrued.

If you are thinking of buying her lingerie, my experience is that this gift is more often a miss than a hit.  Does ‘it’ make her thighs look too big…is it uncomfortable…did you know that breast edges need support…the list goes on.  Gifts for the bedroom are more likely to be seen as a selfish gesture as opposed to an act of love so you probably want to avoid them.

The same can be said for kitchen items, unless you are the one doing the cooking, or vacuums, or car care.  Face it – anything practical – or humorous – is a big risk.

So what works?

First, a word of caution: If you are with a partner who puts a big Valentine’s Day gift or dinner ahead of healthy finances, this might not be the person who you want to spend eternity (or that much money) with.  Get his and hers memberships and move on.

If you have the financial wherewithal, my recommendation (remember that I’m partially clueless on this stuff) is to throw money at the problem…I mean Valentine’s Day.  Take a trip to your partner’s favorite destination.  Bring a private chef to your home that is decorated with your partner’s favorite flowers where her favorite music wafts in the background.

I am pretty sure that chocolate is part of a winning equation.  Champagne can be a good touch as are rose petals in the boudoir.

Above all, smell good.  This does not mean bathing in fragrance.  Smelling clean with a hint of your partner’s favorite scent will attract your partner to you like a fly to…bad example (maybe not for some people).  Also, manscape!  Few people want to hunt for a tree through dense underbrush…and if you can do a bad comb-over using your ear, nose and eyebrow hair, trim those too.  Just as importantly, have good breath.

Simply cleaning up and acting like her dream partner will win you lots of points.

Show courtesy and concern without a hint of sarcasm – even a momentary loss of decorum with a sarcastic or unkind word can ruin the most romantic of settings.

Be everything that your partner thought they were getting when they met you…and then some.  If she thought you were a diamond in the rough when she met you but you have been increasingly looking like cubic zirconium, now is a chance to make things right again.

Haddon Libby is Managing Director of investment advisory firm, Winslow Drake and can be reached at or 213.596.8399.