Dear Sean


All I want this year is for this girl in my third period class to go on a date with me, but she’s way out of my league.

Please help,


I’ll put this in the nicest way I can: If you’re asking me for advice, you are officially up the proverbial creek without a roll of toilet paper.

I am the last guy to ask. When I was fifteen, there was this girl named Chloe. I liked her. And I mean “liked” with a capital L. All I wanted was for Chloe to look longingly into my eyes and utter those few words every boy wants to here: “Let’s purchase real estate together.”

But I didn’t have a chance in twelve hells because I was—follow me closely here—an idiot. Certainly, I wanted to be the sort of guy who could approach a girl, but whenever I was in the same room with even one microgram of estrogen my IQ was reduced to that of a water-heater.

So I asked my older cousin Ed Lee for advice. As it happened, Ed Lee had extensive experience with the opposite sex and had even talked to a girl once in first grade. His suggestion for getting Chloe’s attention was simple:

Let the air out of her mother’s tires.

My cousin’s actual idea was to slightly deflate Chloe’s mother’s tires. Then, when Chloe’s mother drove her to school, one of the tires would go flat. Once the tire flattened—I think you’re catching my drift here—my cousin and I would “happen to be cruising through the area” in my uncle’s 1972 Ford Country Squire station wagon. And we would be heroes.

We would pull over, stride to their car triumphantly, tell the ladies not to be afraid, then like the mechanical-expert beefcakes we were, we would call AAA Roadside Assistance.

Or even better, WE WOULD CHANGE THE TIRE. It was a brilliant plan. And all Ed Lee asked for in return was that I make him my best man.

Here I’d like to pause for a moment to remind younger readers not attempt the following stunt. Remember, I am a trained liberal arts major.

We decided to flatten Chloe’s mom’s tires using a drywall screw. The reason being, with a screw you could adjust the air leak from Fine Trickle to Whoopee Cushion. Whereas with a nail, you were asking for trouble.

Ed Lee figured we needed to start bleeding the tires about two hours before Chloe left for school. So we snuck into her driveway carrying a cordless drill.

And what happened next continues to live in regional lore to this day, and is often discussed in local taverns, bowling alleys, Rotary Club meetings, and wedding receptions throughout Okaloosa and Walton County.

One chilly February morning before school, the sun was low, Chloe and her mother reportedly heard a loud boom in their driveway. Whereupon the family came rushing out of the house to find me and my cousin lying flat on the lawn, covered in bits of black rubber.

The first words that came from Ed Lee’s mouth were: “So, Chole, are you free on Friday night?”

So you don’t need an elaborate plan to get her attention. In fact, plans are bad. You’re probably going to think this is corny, but I read your letter to my wife for her advice. My wife has been female for much of her adult life, and she had an immediate idea.

Her thoughts were: “He should buy her flowers.”

Now I know you’re thinking, “Wait a second, isn’t that too forward? Won’t flowers creep her out?” Relax. They’re flowers not embroidered maternity clothes. A bouquet simply shows a little active appreciation. And if you ask me, we need more men who believe in flowers.

I also talked to my wife’s friend, Linda, who has been a female for quite some time. Linda told me this:

“A love note is the way to go. He doesn’t have to make it sappy, just write something sweet on paper. And whatever he does, DON’T send a text message. Only stupid guys do that.”

It turns out that a lot of women unanimously agree that text-messaging is about as romantic as breaking wind during a unity candle ceremony. Plus, a text can be misinterpreted in a million different ways.

Here’s an example I received from Stephanie (a longtime female). When Stephanie’s grandmother died in the hospital, Stephanie’s mother, Beverly, sent a group text message to her entire extended family to share the news. The text read:

“Granny just left this world at 3:12 P.M., Steve and I were with her, she is no longer with us. LOL!”

You will note Beverly’s closing remark, “LOL!” Complete with an exclamation point. About five seconds after Beverly sent this little baby, she received about 14,203 text replies which said things like:

“This is appalling.”

“Disgusting, Beverly, really?”


And Stephanie’s personal favorite reply: “MOM! Are you smoking crack?”

Beverly later admitted that she always thought “LOL” meant “lots of love.” Of course, anyone under age ninety-six who lives in our current solar system will tell you that LOL means “laughing out loud.” But that’s not the point here. In fact, I don’t know what my point is anymore.

So I’ll wrap up by telling you that I believe in you, champ. More than you know. To love someone is the most important thing you can do with your life. You’ll make lots of mistakes. But being genuine is never a mistake.

And if none of the above ideas work, you could always try the tire thing.


  1. Pamela Sage - December 28, 2019 10:46 am

    Your story was true, candid and encouraging to all readers… giving
    those who are in the same spot you were in, a simple little “nudge of confidence.” Nice read!

  2. Lori - December 28, 2019 12:34 pm


  3. Marilyn - December 28, 2019 12:35 pm

    The flowers sounds like a good plan to me. Most females like the sentiment of flowers. The “tire thing” is definitely not a good idea for anything!

  4. Elizabeth - December 28, 2019 12:55 pm

    So, did Chloe go out with either of you?

  5. Kat - December 28, 2019 1:03 pm

    💕Sean, we love how your columns open up the conversation with others! (8:00 am. eastern time)💕

  6. Shelton A. - December 28, 2019 2:50 pm

    Congrats on blowing up Chloe’s mom’s tire. Flowers always work well with a nice note or card.

  7. Linda Moon - December 28, 2019 4:32 pm

    I was once FIFTEEN-AND-PATHETIC-IN- BIRMINGHAM. But shortly thereafter I was not-so-pathetic-in-Texas. I’ve been a female for my whole life (i.e., a LONG time). Someone threw away or mysteriously misplaced an actual love note sent from a Texan to this Linda (me). You are right, Sean, being genuine is never a mistake. Misplacing a love note from my teen-age life was a mistake of gargantuan proportions, however. But I do love someone, so all is forgiven!!

  8. Harriet - December 28, 2019 4:46 pm


  9. Kelly Joe Ray - January 5, 2020 8:11 pm

    Lots of love in this story Sean…Try writing a poem about her…Shipmate…That never worked for me much But it’s better than the “Tire Trick”…
    here is my first attempt in 7th grade the victim was Cindy Clugston and we dated off an on for three years after this and are still friends 50 years later…

    Roses are red
    Violets are blue
    I think I love you?
    And there ain’t a dang thing
    You can do to about it…

  10. Mary Hicks - February 4, 2020 6:29 pm

    God bless young boys! Thanks again, Sean and God bless you and Jamie.


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