Bring a Damn Sharpie

The irony of this title is I do carry a sharpie, always, multiple colors usually and at least another form of writing utensil. In fact, before posting this, I got asked twice today if I had one…which is odd and I took as a sign to post this story, even though it takes me making myself vulnerable to a new level. This story is a lesson in being prepared but more so, making sure confidence is your second carry on item.

Let me take you back to 2010 – it all started on an American Airlines flight to Minneapolis. I was traveling for work and my boss was joining me on this trip. You see, my boss and I have a unique (READ AS: no boundaries) relationship.  I started working with her at the impressionable age of 20 as her summer intern and essentially grew up under her wing. I would say she is like my mom but she has made that clear on many occasions that although this is biologically possible, she much prefer to be referred to as my “cool” older sister.  She is on the never ending quest to find me a boyfriend, mostly because she would like to quit her job and nanny for me (again no boundaries).

One more important thing to know about my boss Pam is that she is not a huge fan of flying. Although over the years, she has gotten tremendously better, she still has no shame in proclaiming she’s all about a little pre-flight prescription to take the edge off. 

Back to the story  – as the plane had almost completely boarded, I found myself in the middle seat, with Pam on the aisle and an empty window seat to my left.  SCORE.  This was one of the last flights out for the night, so I was essentially hitting the seating jackpot.  As everyone had settled in, on to the plane came a very, very attractive gentleman.  Knowing how this typically goes, I was assured he was walking down the aisle to go sit next to his smoking hot girlfriend who had gotten an earlier boarding group.  But low and behold, the American Airlines seating gods were on my side friends because as Mr. Tall Dark and Handsome, later to be known as Sam, walks down the aisle, he stops at my row and says, “I think that’s my seat”.  SHUT YOUR MOUTH.

I stand up to let our new seat mate take his window seat as my boss elbows me, with absolutely no discretion, and I know her match making wheels were already spinning. Now believe it or not, I am a fairly shy person. I can talk to anyone but when there is any vulnerability or stake in the game, I am a pretty big chicken.  In true Pam fashion, she leans over and asks where he is traveling – duh Pam, this is a last flight out, direct flight… we are ALLLL going to Minneapolis.  With barely a breath in between she blurts out “so do you have a girlfriend”.  Way to ease into that one Pam, real smooth.   Completely caught off guard he says “No..I don’t really have time for one” – which is oddly enough, my go to line as well. I 1000% have time for a boyfriend, it is just an easier response than the Public Service Announcement I feel the need to give to married people about Dating Post-College with Apps and different standards – again, for another blog post.

Pam shrugs it off as a lost cause and no sooner than she can lose interest he says “Actually that’s not true, I just don’t have one, the other is just easier to say”.  MATCH MADE IN TARMAC HEAVEN.  So leaning on Pam to continue what she started, I look over to her…she has a dazed look and passes out. Literally, out cold, medication fully kicked in leaving me and this  stranger who all I know is he is dreamy and has no girlfriend, to fend for ourselves. It was a blessing and a curse because we knew what this looked like – the world’s most inadvertent set-up.

Sam ended up being as charming as he was handsome. We talked books, we talked dating, we talked the downfall of our society thanks to social media.  We found out that we lived in the same small apartment complex on the same floor for an overlapping period of 3 months the summer before. He told me about his family, we talked travel, work, friends. It was easy and it was fun and it felt more comfortable than a lot of dates I had gone on in recent history.  We attempted to play Words with Friends (it was the height of it’s coolness guys, don’t judge) but due to a shawty internet connection (damnit 2010 plane technology get your shit together) it didn’t connect, leaving us to yet another conversation that made me swoon even more.

As Pam was regaining consciousness and we were beginning our final decent, dream boat Sam realized he left his work credit card in the airpot bar.  Melt my heart, a man that loves an airport bar, could he get any better!? 

In typical girly fashion I had approximately 15 minutes to make sure this wasn’t the last time I heard from him.  As I plotted in my seat with literally zero ideas (guys, I never claimed to have a lot of game!) Sam stewed over his corporate card  woes and what he was going to do.  As soon as we landed, he got on the phone to cancel his credit card.  Knowing this was make or break time, I was hoping that this would be a quick call but apparently, customer service at Bank of Who-knows was taking their sweet ass time and RUINING MY LIFE by keeping Sam on hold.  As row after row was deplaning and my dreams of Sam proposing (obviously the next step in this equation) were slipping away I decided to take matters into my own hands.  I would channel my inner Carrie Bradshaw and give him my number oh so coyly on my plane ticket, like I do this all the time.  I have done this approximately never times.  All a good plan in theory until I realize we are the next aisle to leave AND I DON’T HAVE A PEN.  I had nine different scents of hand sanitizer and approximately eighteen varieties of snack packs but I couldn’t find a writing utensil to save my life. The clock was ticking, he was talking to customer service agents, he was being transferred, they were checking action on his card – oh my GOD, I was thinking, I will pay the balance if you just let this man just get off the phone!  So as Sam left the aisle, still on the phone, my heart sank a little, consoling myself with at least the memory of an enjoyable flight. I retrieved my overhead bag and left the plane. 

But low and behold, who was standing there waiting on the jet bridge, STILL ON HOLD (seriously, can I get a comment card for this credit card company!?) was Sam.  It was the makings of a missed connection in a movie, we were blocking the jet way, he was on the phone, my boss was anxiously heading down the jet bridge and we were like two ships passing, wanting to connect but it was too much too quick.  He grabbed my hand and said “it was really great to meet you, I guess I will talk to you…” and stammered a little and blurted out “on Words With Friends?”…. OMG hand to forehead.  I think as soon as he said it he knew how dorky it was. I definitely knew how dorky it was and didn’t even care.  But again due to American Airlines in-flight internet trying to derail fate, the internet never connected in flight, our names were never saved and I never heard from Dream Boat Sam.  

Lessons from Dream Boat Sam:

1.  Whether Sam was the love of my life or just a great guy that was able to hold good conversation (a rarity these days BTW) and a gentleman, I should have put my pride and fear aside.  Who cares if I seemed weird waiting and tell him “you were fun to chat with, call me next time you are in Phoenix”.  It wouldn’t have been odd at all, but being young and thinking things happen like they do in the movies, I was blinded by stupidity and let a chance slip away.  Fear of rejection, even from a stranger, is funny that way. I would have been the only one that knew, it wouldn’t have mattered and only something good could have come out of it, even if it was just a lesson.  Regret and “what if” is way worse than no phone call.

1.   Bring a damn sharpie!!