Growing up as a child in the 80’s there are two rules of thumb you learn early on, nearly after you learn how to walk; Don’t talk to strangers and Don’t take candy from strangers.

With the unfortunate story of Adam Walsh long behind us in the past, one can easily overlook these golden rules, even as they apply to us in adult life.  So, yes, as a Jetsetter, I’m ever the wise not to accept drinks…aka “adult candy” from strangers, yet as a Gypsy, I’m a bit guilty of talking to strangers, so the time has come for me to relearn this childhood lesson.

While exploring the uber safe streets of the Back Bay and South Side neighborhoods of Boston on a recent afternoon, a typical occurrence happened to me.   Minding my own business, fully equipped in a hat, dark sunglasses and a blackberry in hand, as to ward off any possible approachers, I found myself chatting with a random guy walking along side of me on the street.

Did I solicit this attention you may ask?  Of course not!!!  He “liked my look” and complimented me on my leopard tights and my copper colored Isabella Fiore handbag.  I guess dead giveaways that I was not from the area, being that the other women spotted on the streets were working the super preppy look.  The fashion talk was a bit of a weak spot for me, and his “In”.

Boston is now about the 5^th city in 2 months where I’m clearly heading somewhere, mid day, albeit alone, and someone starts walking along with me.   I’ll give this character one thing, he was not shady at all, a decent guy, nicely dressed and just trying to make conversation with the rare bird.  Whether it was my overall tiredness from my extreme travel schedule or his persistence in the conversation, I abandoned my typical routine of making zero eye contact, slightly picking up the pace and remaining stone faced at any witty comments and actually began to answer his questions…nothing too close to home though.

Of course I can attribute it to a bit of the “New Girl Syndrome”, but this one could not take a hint at my agenda.

Following me into the restaurant when I thought the conversation was over, but I guess it was not technically “dead” and sitting there, speaking to me at the bar, while we dined for 2 hours, my laptop open all the while and my repetitive glances and typing efforts, as my subtle hint that I wasn’t interested, were never caught.  Finally, due to my being one of the slowest eaters in the world, I claimed my victory without having to say the harsh words of “Get Lost!”

In the end, I was able to enjoy the last hour of my lunch at The Butcher Shop, as well as take care of a bit of work on my computer.  Exactly what I had endeavored to do from the beginning.  The rest of my afternoon was spent enjoyably wandering in and out of the neighborhood streets and popping into boutiques here and there.

Later that evening, joined by my younger Boston resident cousin, Crysta, we set out to enjoy a fantastic, multi course dinner at Hamersley’s Bistro followed by numerous mixology style drinks and live music at The BeeHive.  She decided to call it a night a bit early by my standards, 1:30 am, but quite on par for this town, yet the night owl in me still wanted to see one more place.

On my walk home, I stopped off at Lolita, a chic bar and lounge characterized by dark shades of red and black chandeliers.  Having passed the place a couple of times already I knew I wanted to check it out.  The crowd was great, although it was beginning to thin out due to the hour, but it was certainly worth one drink.

At the bar, immediately after ordering my sauvignon blanc, the two guys to my right began to chat me up.  As I started to face them, much to my horror, directly behind them was “The Character” from earlier in the day, looking in the other direction by grace of god, and chatting up another woman.  It felt like infinity until the bartender brought me my change, and these guys probably thought that I was schizophrenic asking them to angle their bodies in a way that created a direct wall between my stalker and I.

Luckily I was able to settle up my bill and with a little creative bobbing and weaving, make my way from the bar to the back lounge room without being sighted.   Here, safely concealed from the eyes of “The Character” I was able to relax, enjoy my drink and what else…talk to a group of strangers for the rest of the night.  I guess there’s one lesson that this Gypsy will never learn.