A Thirty Year Old Box of Dreams: Shoulda, Coulda, Woulda, and The Side-Effects of Sticktoitiveness

I’m a pack rat. I tend to hold onto things way too long for two reasons: sentimental value or for evidence.

I actually carried around the red patent leather roller skates I had as a kid until I was twenty-three years old. I loved those things. There was never another pair of them on anybody’s feet any time I went skating. A gift from my Dad. One important enough for him to write my name, address, and phone number in with black magic marker. They made me feel special. I now wish I had them… for what I have no idea?

And, as a scapegoated, chronically gaslit person, I’ve saved things for evidence — as to who said what, and who did what— so as to have my dates, times, and years correct when writing/talking about them.

The silver box pictured above is thirty years old. It hold letters and cassette tapes from a pen pal I had in the 90’s. I pulled it out to investigate the contents two years ago in November, right before National novel writing month 2019.

This is what I wrote about it in a FB status:

I sat listening to cassette tapes I had from a pen pal in England back in the 90’s last night. For almost 30 years I’ve carted this box of cassette tapes and letters around with me everywhere I’ve ever moved. And I’ve moved a lot. We wrote from 1990-1993. I would sometimes look at the box and wonder why I still kept it? I wondered if I’d ever get a cassette player to listen to them? Did they still make cassette players? But, I decided I wanted to listen to them before getting back to writing my second memoir that time period. I wanted to jog my memories and give me some semblance of what was going on in my life at the time before getting back to it in November… and let me tell you, I not only cried, I wept. It was like opening a time capsule and learning about my twenty-three year old self from someone I never got to meet. My penpal was a boy named Tim. And I was a dental hygienist assistant at the time raising a five year old son alone. And having his letters were the most exciting part of my life then.

On the tapes, he would go through my letters, (I’d hear him shuffling through page after page as the birds sang in the background…) and he’d answer my questions as he commented on things I had written about: losing my dental job due to downsizing, not having a phone due to the cost, but telling him he could call my mom’s house for me on a certain date and time if we planned it ahead of time, apologizing for taking so long to write due to not having stamps. God, times were so hard, I don’t know how in the hell I even made it back then.

He reminded me of a painting he made for me that he had shipped, and although I remembered it, and could picture it vividly, I do not have the painting and do not know what happened to it? It was the silhouette of three African women walking off into the sunset with two children in tow. One was balancing a basket on her head. The painting had vibrant yellows, oranges, and reds with contrasting black, and was framed with a black border and acrylic frame. He entitled the painting, ”Going Back to The Village.” — Don’t you think that would make an excellent title for memoir #2, where I write about single motherhood and all that entails? — I sure do!

He commented on sending me something to wear, and I had forgotten it was a jacket, that I can’t for the life of me remember, and no longer have either. He talked about all the places he visited in Europe; Norway, Sweden, Italy, Belgium, Tunisia, Spain, Greece, Portugal, Canary Islands, Holland, Denmark, Switzerland and on, and on. We were the same age and he had done all this living. That made me cry and drove home the point that I’ve never not lived my life for someone else.

He talked about how he wanted to come visit and stay for 3-4 weeks. But, by that time, and after writing for years, I had gotten a boyfriend who wasn’t too keen on the idea, so I told him he couldn’t come, and that was the end of our writing and through-the-mail romance.

If I could go back in time and kick my own ass, I certainly would. I was furious with myself all over again, and it’s something I’ve regretted to this day. Not only have I not lived at any time for anyone but others, but I’ve allowed men to dictate and have willingly wrapped myself around whatever it was they decided they wanted. I sobbed like my life was over last night. Like I’m a walking zombie with no god damn life. I couldn’t believe all my life was reduced to this moment. Something has to change…

Today, I will read through the rest of his letters and write down things to remember from them. What TV shows and movies were popular over there then, what music he liked, and learn more about what my stupid-assed, twenty something self was, and wasn’t doing then. I’ll tell ya, I was existing and not living, that’s what. And, it made me realize, I’m still doing some of that today.

It was surreal to hear the progression of tapes and letters go from a friendship, to a full- blown romance and falling in love through the post. It was my own little slice of heaven to savor last night and I’m ever so grateful I never threw that box away.” 🎁

I found Tim on FB that same day. I sent a friend request and he accepted it. He married late in life, like he told me he would in his letters. He was still as gorgeous as ever; a model in fact, and his wife a real beauty. I longingly looked at the wedding pictures he posted taken in a beautiful English church cathedral, complete with horse drawn carriage, and a big smiling family. And I wondered how different my life would be had I allowed him to visit and continue to sweep me off my feet.

Ironically enough, I (yet again) have a pen pal in England who lives a short distance to where Tim does. I was partnered with her from a group I joined on FB. I chuckled when I found out she was in the U.K. and wondered why that place was coming back to me again? And since writing and having a pen pal is so much easier than it used to be, she wrote to me today telling me how my words stirred in her such emotions about her own life choices that she disappeared into herself for awhile and reflected on her own life choices.

She knows more about me than anyone and she wants me to visit there someday to put away the ghosts of the past. Until then, she wanted to know if there was a message I’d like for her to give him if she runs into him at his tea shop.

“Yes. Tell him my not meeting him is the biggest regret of my life. He was a bright spot in some of my darkest days.”

So much of our longings in life are buried under obligation, roles, and responsibilities and other people’s expectations. And when you show up for those roles and expectations 150% in life, and things still don’t turn out as planned, well it’s enough to make you want to give up. It makes one want to scream at the sky, “What more do you want from me!?”

I have a good life in so many ways, but admittedly, I do still feel bitter at times. Everything I thought I was doing right, is now wrong. Everything I lived for then, gone.

I live in a 55+community now, (in which I am luckily still too young to be living in by one year,) in a comfortable, quiet, long-term marriage, in a beautiful home, where now, the most unpredictable thing is whose health will fail first? Sad, but true. At this stage of life, we constantly try to find the good, the positive, the silver lining because to do anything else would be miserable.

I still continue looking for my purpose in between workouts, cooking dinner, and walking the dog. And writing memoir still calls to me. Daily. — People say I’m good at it. It’s where I find my youthful strength again. God, I was so strong!

But, sometimes I wonder if writing about the past prevents me from living the life in front of me now? Then, out of guilt, I get busy adding more and more to the to-do list looking for me… as if to say, “I know I’m in here somewhere?” I search in yet another writing course, another art project, another self-improvement book, another goal.

I live a mundane existence now, really. There is nowhere to be, and no one needs me. I’m chronically ill, although I don’t look it. I could stay in my pajamas for days and eat a bowl of popcorn for dinner if I wanted. And some days I have. Some days I resent it. And yet, at other times in life I would have killed to have my life now. It’s quiet, calm, but also full of pain, loss, and a lot of grief. Loss of family, career, home, children, friends, dreams, health and our youth… most of which has to be dealt with all at the same time. Sometimes it’s all too much and still other days, I like it fine. I’m happy to be gaining the wisdom that aging brings.

My husband, who was the one to surprise me with the cassette player for the purpose of listening to these old tapes, sat and listened with me too, and he thought they were so cool. He sat smiling. He laughed. He said, “that’s my girl.” And, he comforted me when I sobbed for my younger stressed out self. “All those sacrifices… for what?!” I cried. He said he wished he’d known me then…

It opened a good conversation where he reminisced about girls who broke his heart, his mistakes in life, things he wishes he’d never done, and the times he had to break his own heart. We sat laughing and crying together on the floor of my craft room.

All in all we’re both happy that we have had stick-to-it-tive-ness and grit to stay the courses we’ve chosen. And yet, other times we wonder if that’s been a good thing? There’s so much I should have given up on… put my foot down on sooner than I did… him being one of them; there’s so much he shouldn’t have done… so much I should have, he could have, done differently. All of which has brought us here with each other; a place that we both love and resent at times.

Sometimes this life is enough and contentment creeps in the back door to give us a deep rest from longing and looking. We’re happy to listen to the same stories we’ve heard again and again, sit and mindlessly watch 90-Day Fiancé reruns for the umpteenth time or to create yet another Pinterest board on finding the beauty in gray hair and dressing to disguise a menopausal tummy.

And then… if you’re a oak rat like me, you open a thirty year old box of tapes and letters and find yourself asking, “What if I had done this…? Should I have done that…? And was it all worth it?”

And then, after feeling it all, you dry your tears, box up your youth and decide to get up and go work through all those what-ifs, should haves and could haves, by going to the gym, going for a walk, or just sitting with the fact that you’re pretty certain this is how everybody feels from time to time in life. It’s the side effects of stick-to-it-time-ness. Of a long-term marriage. Of aging. Of having kids who are adults who no longer resemble anybody you actually know. Of putting yourself on the back burner.

What do you think?

How do you show up for your roles and responsibilities and not put your own needs last? Can it be done?

Do you think people are happier when they live for just themselves? Or, are we happier when we dedicate our lives to caring for others? Is there a way to do both? To have our cake and eat it too? Is there ever a way of living that produces no regrets? Is being present in the now always possible? Or selfish? Is not giving up a good trait to have in life? Isn’t it human nature to dream and look longingly to the past? Or in not doing so, would that mean we end up like this guy? 👇🏻


If you’re a scapegoat, what have you held onto for sentimental reasons? What have you held onto for evidence? Are you sentimental because you’re a scapegoat or do you think you’re a scapegoat because you’re sentimental? Do you listen to your intuition when getting rid of or holding onto items? What do you need to let go of? Hold onto? What do you need to label with your name and address? What do you need to be done with once and for all?

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