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How I Met My Retirement Episode 4

An Unlikely Friendship and an Unofficial Shoe Store Boondoggle

By Debra Flanagan, Macaroni Kid Chicago Northside September 15, 2021

I worked at the local shoe store, part-time, after school, for two years.  During my senior year, one of the most popular girls at school applied to be another cashier.

She was a beautiful girl. She was quiet, but she knew how to carry herself, and she was always surrounded by a clique of the toughest girls in school.  Girls you did not want to mess with.  They dressed a little provocatively for teens, but exuded so much self-confidence that even the boys were afraid to approach them.  She was the only one, in the group, who had a serious, steady, boyfriend.  I must admit, I was pretty intimidated by her.  I was under the impression that if she didn't like you, or you looked at her or her boyfriend the wrong way, she might sic one of her henchmen on you.  So when she got the job, I was a bit anxious.  

Winds up, I was completely wrong about her.  It took a little while to warm up to each other, and though we never hung out at school, we did become friends.  She had friends in college (of course she did) and she brought me to some dorm parties.  People would always be asking her, what I was doing there.  I certainly had no idea.  Though she had all these very cool, older friends, she was very innocent herself, and incredibly sweet.  When my first real boyfriend broke up with me, she came to my aid.  She brought me into the stockroom at work, with a bag of hair and make-up supplies and gave me a make-over, all the while convincing me that I was too good for him, etc.  It really made me feel better.  Yet, when we saw each other in the hallways at school, we would always just say hello very subtly and continue walking.  

One day, she came to work and told me, and the other ladies, that one of her older friends who worked for an airline was going to give her free tickets to go to St. Croix for spring break, and asked if we wanted to go.  I didn't even think to ask how they were, or why they were, giving her free tickets.  In retrospect, this was very fishy, however, we all jumped at the chance.  My Mom, who was always supportive of me travelling, never asked any questions either.  The girl had an aunt in St. Croix that we would stay with.  I really don't know how this ever happened, as my parents never even spoke to hers.  The night before our flight, we all slept over at her home. Her home was humble, her father was blind, she was super respectful of her parents.  Again, nothing matched the original image I had of this person.

The next day, we all called in sick to work.  Even to this day, I still regret that we left our kind manager in that position.  He had to man the whole store by himself for a week.  It was terribly inconsiderate, but I will chalk it up to my not-yet-fully developed brain.

We had an amazing trip!  I barely remember even seeing my friend's aunt.  We went to the beach, restaurants, and dance clubs til all hours of the night.  The girls wore bikinis and sunned themselves to achieve perfectly tanned, olive, skin.  And then there was me with my paler than pale skin, just roasting.  Again people would ask the other girls, "Is she really with you?"  A young MAN, interested in my HIGH SCHOOL, friend, took us all out for a lobster dinner one night.  Now, I shudder to think of all the ways in which this could have gone very badly, but it didn't.  Two high school students, one college freshman, and an equally young mom, all had an unscathed week in paradise.

When we got back to work, our manager was infuriated.  Between my sunburn, and the others' tans, it was fairly obvious that we had gone somewhere together. For a few weeks, he mumbled under his breath, but he never fired any of us.  

Once we all stopped working at the shoe store, the friendships dissolved.  I did see my one friend at a high school reunion. Sure enough, she married her high school sweetheart.  She was once again surrounded by her old crowd, and we didn't speak.  I wonder if her crew ever even knew about our trip.  

When I retell this story to my kids, I focus on how leaving our manager in the lurch was the wrong thing to do.  I also talk about my unlikely friendship and how they should never judge a book by its cover.  I also emphasize that they will NEVER be allowed to go to a tropical island by themselves in high school!


Need to catch up:

Prologue

Episode 1

Episode 2

Episode 3 


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