On Sailboats and Awkwardness

I saw Shirley working the hand drill, putting the mast way too far forward.  I looked down at my boat with its perfectly placed mast-hole and I wanted to help her.  Her boat probably wouldn’t even float, let alone sail, if I didn’t show her where to put the mast-hole.

I even stood up from my chair and had a mock-conversation in my head:  “Shirley, you probably want to drill that hole back toward the middle.  That way your regatta boat can hold both sails, instead of just one.”

“Oh thank you, Jimmy!” she responded in my head.  “I always knew you were smart, but thank you for being so helpful and cute, too!”

I blushed and steeled my resolve.  I walked toward her desk.  I had to hurry, she was just about to drill the hole.  I was about two steps away when she started to turn the crank.  I walked right up to her.  She looked at me, all curly-haired and tan, the prettiest girl in the whole of Mr. Schaeffer’s 4th grade class.  And I walked right past her to the drinking fountain.

I heard her drill going as I took a too-long drink, letting the water run into and out of my mouth as I tried to see her out of the corner of my eye, knowing that I could have helped her if she was just a little less cute and wondering what had happened to me.

When I was really young, I could talk to all the girls.  I’d go right up to show them my eyepatch or new glasses, my jumping skills or big belly; and, if they were truly beautiful, I’d show them all four.

I talked up the belly that day because my socks were nothing special.

I gave away kisses left and right.  I proposed to the babysitter’s daughter who, at 22, was 18 years older than me.

And more than one lucky lady tried to kiss me, too.

My joke was so funny, she couldn't help herself.

And then, around Kindergarten, the girls became more beautiful and my eyepatch confidence waned.  I began passive bragging and sly stunts to get their attention.  I learned hopscotch, tripped on purpose, and, for the prettiest girls, ate sand.

The night before the regatta, I thought of the comforting words I would give Shirley and her ridiculous looking ship after she lost.  I would hide my blue ribbon and say, “That was a good effort, Shirley.”  And she would say, “How did your boat do?”  I’d respond, sheepishly, “Well, I won first prize, but I was lucky.”  And then she’d say, “Oh Jimmy, I always knew you were smart, but thank you for being so humble and cute!”

Zach went to a one-year-old’s birthday party yesterday.  He played it smooth at first, taking her toys away from her and crawling away.  But then he crawled to her, played peek-a-boo around the coffee table, and laughed.

A chip off the ole block.

My boat went about twenty feet and started to sink.  One of the teacher’s rescued it and brought it back to me.  Shirley came in second.

And she didn’t say anything about my effort.

Good old Topeka 17; I build this in 1984. One sail is busted and the second one is barely hanging on, but you can still read 'JHG' on the side of it.

About Jimmy

The stories herein are about a sentimental 80s child who cried at every showing of ET (the sad part where he was lying in the wash) and his families, then and now. His wife, son, parents, and siblings play their parts well. They have their exits and their entrances. Sometimes their exits are sad, but not as sad as ET.
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16 Responses to On Sailboats and Awkwardness

  1. inkline says:

    At least so far I’m the only girl Zach kisses.
    This story kind of reminds me of all the times you’ve talked BEFORE games about how I should probably let you give me some advice on strategy…and then AFTER the game, I don’t really say anything. But you give me a kiss. Because the winner always gets a kiss.

  2. Dor says:

    I simply don’t know how you can regress so perfectly and become 4 years old again! This is such a delightful story and as always, you make me laugh out loud.

  3. Dianna says:

    Another great post. I think it’s cool that you stlil have the boat.

  4. lessonsinbrokeness says:

    I enjoyed this, very well written and as you may or may not have read, I too enjoy boats. For me rather they are ships of days ago. My father bought me one similar to the picture when I was a wee lad. Thank you for the memories reminded in this.

  5. Sachi says:

    Loved this post ! 🙂

  6. Mom says:

    You were always painfully shy as a little boy, but look at you now. You exude confidence, even when you shouldn’t. Funny how things work out.

  7. magsx2 says:

    I can’t believe you have still got your boat that is amazing, well done. 😀

  8. Snoring Dog Studio says:

    What a lovely story. It all starts so early, doesn’t it – this dance of the mating game!

  9. 1smiles says:

    Life has a way of getting us balanced doesn’t it? Good effort and a kind heart you had even as a young boy. Great post!

  10. gigoid says:

    Very poignant; you have a nice, clear style that’s very friendly. Good post…..you seem to have a good grasp of the Bozo that lives in all of us, and a wry sense of humor. I look forward to more memories from your past…..

  11. Maxi Malone says:

    I’m with gigoid, you have a way to remind us of the Bozo that lives within everyone. Thank you for this one, Jimmy. Life has been dishin’ it out lately and I needed a good laugh.

    Blessings – Maxi

  12. Jane Thorne says:

    Hello Jimmy I love your blog and have passed the Liebster Award onto you..here’s the link http://wp.me/p1l7Si-xB – love to you, Jane x

  13. Ah, the many times that I “burbled” water out of the side of my mouth during a fake water fountain stop. Thanks, as always, for bringing back so many memories!

  14. Adrienne says:

    Your ability to write about your own childhood and weave it together with what you’re living now is so refreshing and captivating. I always save your posts and read a few at a time….I pretend they’re a book (hint hint)! I LOVE that you still have that boat….and that your mom chimes in after your posts!

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