Optimistically looking forward to my upcoming trip to Madrid, a mere 2 weeks ago, I posted on my Jetsetter Gypsy Facebook page an image of a large Victoria’s Secret shopping bag sitting atop my dining room table with the caption “The necessities for my upcoming trip to Madrid, Spain”.  

Yes, the entire contents of this bag were transferred into my large checked piece of luggage and ended up occupying about ¼ of my personal cargo, but the ideas and possibilities that they represented occupied a much larger portion of my brain.

This was the second time in my life that I’ve traveled to Madrid carrying along with me such accessories for “indoor entertainment” and it was being done with mixed emotions, excitement and possibilities surely representing the majority, but also a touch of nerves based on a rocky history of packing these contents.

Having stepped across the friendship line about a month prior to my trip with one Barcelona based friend, our long distance chats turned romance were about to become a reality or at least live and in person in a few short days.  Not being one to typically cross that line with male friends, I had no idea what to expect, having only done these long distance style flirtations with guys I’ve dated, which has turned up to be a bit of a mixed bag, I was optimistic at least to be making plans with someone whom I shared a mutual level of trust and respect.

So as I boarded my plane to cross the Atlantic this time, I could only think of past experiences of packing these sexy goods in my luggage and how this time had to be better.

My original experience in this realm was 8 years ago, travelling to Kauai, Hawaii, while in one of the a major relationships of my life, yet one that was relatively doomed from nearly that same point. These seductive pieces, most of which never got worn on the trip were certainly not responsible for the arguments and stressful situations that we encountered along the way, even when we were situated at one of the most amazing resorts in the world, the St. Regis Princeville, but perhaps this was the beginning of a pattern.

Two years later, towards the end of that same relationship, we made one last attempt to revive our flames and headed to Negril, Jamaica.  Having not refreshed my lingerie wardrobe in a major way since the Hawaii trip 2 years prior, I decided to do a little pre travel shopping.  Although at this point we were beyond the bickering stages of the relationship, Negril was more filled with getting drunk on pina coladas and other tropical beverages during the day at our resort Rock House, then heading out for dinner and more drinks later.  Pretty much carrying on as we both knew the relationship was over, but consuming mass quantities of alcohol to just mask over the issue at hand.  In the end, some of the lingerie was worn, but neither of us would remember any of the details.

A more positive outcome was certainly achieved a couple of years back when I headed to Madrid to meet a lovely guy whom I had a more or less long distance connection with for months.  The trip itself was magical as we shared great companionship exploring the cultural side of the city together and chemistry was sparked at night.  Once we returned to our lives on opposite ends of the world the conversation immediately dropped off, as in total silence, for nearly a month, ending the magic of that fairy tale, yet a tiny voice inside my head was a bit relieved for this, as our backgrounds were so different that I didn’t know how things could really work out.

Then most recently, I did happen make plans with one flirtatious “international playboy”, one well know personality in the Baltic States who now shares a similar career as myself.  The plan was for me to fly over to Slovenia to spend some time with him in his home country, after my hosting friends in Barcelona.  This one never even materialized, as the plane flight was booked and the lingerie purchased, but his flaky behavior just posed as too large of a red flag for me to actually board the flight.

All in all, not a great track record for these lingerie inspired romantic travels.  The truth is though, apart from Hawaii, which feels like a lifetime ago…. the others truly didn’t have my heart in terms of long-term relationship intentions.  But these intentions clearly existed on my end from the moment that my Barcelona friend and I made the switch, albeit virtually from friendship to relationship, and we’re not talking “friends with benefits”.

So, once arriving in Madrid, I checked into my suite at the Westin Palace, went for a run through Parque del Buen Retiro, had dinner with friends at my favorite Galician tavern style restaurant Taberna La Maceira and drinks at The Roof Lounge at the Me by Melia, all while exchanging a few more flirty messages prior to his arrival the next day.

Being that this was primarily a business trip for both of us, we had full agendas from the start, including late night client dinners, but I was thoroughly shocked to say that in the end, the only time that we did cross paths was at a work related event, and neither of us are the type to show emotions in front of clientele.

Never the pursuant type in relationships, especially in the beginning, I stayed patient hoping that he’d suggest dinner, send a message to meet up for a coffee, or something just to connect in person, but nothing at all ever happened.  Apart from being the non-pursuant type, I also have a strong belief that if a man wants to be with a woman, he finds a way to make it work, so in this case I was left truly baffled.

Why would a friend choose to cross that line virtually and grow something via communications for over a month, if they never had the intentions to follow through in person, especially when this topic had been discussed?  Was this a case of loneliness or the convenience of a few harmless flirty messages going a little further than planned?  Perhaps!  Could it be that the right intentions existed all along, yet were overshadowed by the burdens of an incredibly hectic work schedule?  Doubtful!  Or quite possibly, could the underlying awareness of a suitcase full of lingerie have created a pressure on the relationship before it even truly got a chance to start, ie…relationship suicide?  I guess we’ll never know!

What I do know is with Valentines Day right around the corner and a new “Indoor Entertaining” wardrobe in hand, I’m optimistic that these garments will soon be put to good use!