I'm past the 40 year old mark by five, and have three failed major relationships. (Four, if you count Johnny Jenner in eleventh grade.) You might think that I'm defining myself by relationships or failure or relationship failure but that's not it. I've noticed that the first thing people always want to know is if I'm in a relationships. Are you with a guy? Why not? What's your history? Like it's the only thing that matters, the single golden thread in the fabric of your life. I don't know, maybe it is.

My last relationship was the best and the worst. We had a son. But we were on the downslide to it being over when I got pregnant. He got mad right away, while I was still clutching the pee stick. A couple years later we quit for real, because as it turns out that schoolground saying about sticks and stones is untrue. I have this tendency to think that a relationship should weather all storms, like a Mormon couple in a covered wagon heading west thru blizzards, up sheer trails through giant mountains and sharing sustenance out of a tin cup. Turns out, nobody else thinks like that.

And it's been another four years after that particularly dismal and long-winded breakup and my life now evolves into a humdrum of work, home, and errands. I teach third grade at in a high risk school and for summer fun I usually work on the house, gardening and canning, and taking my turn donning the emergency aid fanny pack and making rounds on Neighborhood Watch Patrol.  And I enjoy the media arts, you know, TV.

I filled out a .com dating site. Likes: "A good dill pickle." Dislikes: "TV commercials and when Netflix stops mid-show." How bad would my competition have to be for me to win the good-looking guy? The online relationship pool is packed with self-reported big game hunters, mountain climbers, Navy Seal types, models, writers, actors, and Olympic hopefuls, and to hear them tell it every single one of them supposedly overflowing with energy and optimism and greater good projects, saving whales or cleaning up pollution or peace in the Middle East. Plus they all got a crackerjack profile pic. Where  are these people and how did anyone let these relationship treasures get away?

But when it looks like nothing will change, it does anyway.

It was my last day of school and I met my best friend, Piper, afterwards for giant peach margaritas. The margaritas at Marco's are personal swimming pools of tequila, triple sec, and fresh peach juice this time of year and everyone sparkles love in their eyes at the waiter when he brings the one as though life is a grand party and everone is pretty. Piper has a lot of brilliant ideas like this.

Piper and her husband Harold teach at the inner city school Winnona Elementary, same job as me, but unlike me because they are from well-off families, did the "Teach for America" thing for two year  after getting their graduate degrees in teaching and actually want to save the world, at least for a while longer. I, on the other hand, got an English lit degree, couldn't find a job, went back and got a master's degree in English lit, couldn't find a job and then got a teaching certificate and took a job at the crappiest elementary school in Miami.

Piper is a hoot and a hollar because she is fearless, has an acid tongue, and a heart of gold so she gets in all kinds of trouble that rolls right off her. But she is psychologically bulletproof because she was raised with so much money and love that failure and rejection weren't even options. Shameless in a good way, like her brain doesn't recognize these things, can't predict them, and therefore can't fear them so all of that fear  that forms the powertrain of our cautious natures never existed for her. Everyone should have a friend like her. Better yet, be her. But for most of us that isn't in the cards we were dealt.

Turned out that she and her husband and kids decided  to spend the summer at her in-laws Kennedyesque summer home in Maine (complete with domestic help) and wanted to take my son. Fishing. Boating. Jet skis. Private planes. Swimming. Horses. Campfires. S'mores. And meeting kids from families of senators, a software tycoon and a famous chef with eight restaurants. And they wanted me to use their Key West cottage while they were gone. Ten weeks. I dithered and worried about my garden and my canning projects until she leaned over the table, eyes blazing with alcohol and mischief, her thick-tongued words slurred, and said, "What the hell are you waiting for Maddie... When are you going to live? By the time your son gets to college you'll be 60... and then what? You can get hooked up with a 70 year old Grandpa Christmas on geezer.com? You are going to be one bitter old lady with a cupboard full of pickles and jam... bitter as gall! She popped her eyes at me humorously and then she rocked back in the booth and hooted with drunken laugher at her own wit. And I heard myself laugh a little too loud and long too. I'm pretty sure that there was some hysteria in there.

By 5 AM her husband was good-naturedly beeping a tune on the 2016 Escalade's horn outside the house and I was scrambling to get the last of Job's six year old things into his duffle and kissing him goodbye and suddenly he was gone. The house was so still I could hardly breath.

No time for reconsideration. Big day ahead. A lot to do. I don't like to drive and I had to drive over the ocean. Better not to think about it, just do it when I get there.

I pulled a bag off the closet shelf and started throwing my wardrobe into the bag. I took a fast shower and started rummaging through the suitcase to find something to wear. I stopped and Piper's challenge rang in my ears "When are you going to live?" It looked like, no it was a coffin full of worn out black stretchy material. Once you get on the bandwagon of stretchy shifts and tunics and infinitely stretchy leggings in black or cement grey, you're a gonner. They were merged into one dismal blob. Piper's remarks burned. She was right.

Screw it. I used to be fun. I could buy new stuff. What are 401K plans for anyways if you can't live a little. I slid their house key on my car key ring and stared at my to-do list which I made sitting on the toilet, still a little drunk, last night. By late afternoon I was on Highway 1, the 113 mile highway to the Keys, crossing part of the Atlantic by car with a three bags of groceries from Safeway, a paper map in case my GPS went out, a deluxe first aid kit, plenty of bug kill spray, and all my vitamins feeling quite adventurous.