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. Robert mottet - December 30, 2022 11:44 am

    Been there done that.

  2. Keloth Anne - December 30, 2022 12:12 pm

    You and Ed Lee have the best stories—what a visual 🤣

  3. Matt Ovaska - December 30, 2022 12:12 pm

    I picked out the biggest flower arrangement in Publix supermarket for my mom’s 90th birthday. As I was heading to the check out, 3 different men saw me with the flowers and said to me. Wow, What did you do? (true story)

  4. Tim - December 30, 2022 12:16 pm

    I never get “Tired” of reading your stories.
    I was 15 once (upon a time – a long once upon a time ago) and was as inept as you.
    First date was High School prom and didn’t even get a goodnight kiss.
    We are still friends to this day. I know (and love) her kids. They are not mine btw. life & procreation (I’m Pro-creation btw) kinda works that way.

    Pistols and Stay-mins in the plant world (AKA – stay away man, with that pistol of yours in the human world).
    I don’t even own a firearm.

    Anyhoo – been happily married (most of the time) for the better part of 3 decades, so there is hope kid.
    BTW – after the better part of 3 decades, I’ve heard “stay away man with that pistol of yours” many times”.

    That said, we do have 3 wonderful adult kids.
    I guess my betrothed just didn’t want 4.

    Hang in there champ.
    it gets better.

  5. Joy Jacobs - December 30, 2022 12:37 pm

    LOL ❤️

  6. mccutchen52 - December 30, 2022 12:50 pm

    Nothing better than a few words from the wise.

  7. Anne Arthur - December 30, 2022 2:43 pm

    LOL, oh Sean, your stories are just too good. LOL

  8. Janet Wallace - December 30, 2022 3:38 pm

    Great Story! The LOL had me “Laughing Out Loud” because I too for a many years thought it meant “Lots of Love”. A sister finally set me straight as she “Laughed Out Loud” at me.

  9. Eve - December 30, 2022 4:13 pm

    Great comedic writing . Hysterical.

    From a daily reader who has been female for much of my adult life. LOL

  10. Peggy M. Windham - December 30, 2022 4:23 pm

    LOL!! That’s hysterical!! You made my day!! I needed a good laugh! 💜🤣💜

  11. Melissa Brown - December 30, 2022 5:01 pm

    I hate to admit it but until just a few years ago l always thought LOL meant “ lots of love “. I know l am the most stupid person and am not tech savvy. I love your stories – you are a wonderful writer & story teller. Sean, l hope you will continue to greet me each morning with a delightful story.

  12. Karen Snyder - December 30, 2022 7:08 pm

    This is precious, and timeless! Thanks, Sean. To that young man, I would say that he who hesitates is lost. Just ask already, ’cause what’s the worst possible outcome? She might say no, but maybe, just maybe . . .

  13. Harriet White - December 30, 2022 7:12 pm


  14. kingswaydaughter - December 30, 2022 7:30 pm

    My husband’s opening line when I first met him on the telephone was one I heard every day on the first day of school my entire life, and it went over like a lead balloon. I worked in a real estate office and had an ad in the newspaper to rent a townhouse duplex unit. My name is Shawn (my mom left an ‘a’ off the end of that), and yes I have been a female all my life. After answering the phone with a greeting, he asked for Shawn, and I said he was speaking to her. And then it came, “Oh, I thought you would be a guy.” Heard that line my entire life – still do sometimes, but as I have aged, I’m more relaxed about it. After meeting him, it got more irritating and then funny and then interesting. As time went on I broke my number one rule – don’t get involved personally with a tenant. I eventually married him, and 41 years later, the knot is still tied.

  15. davidpbfeder - December 30, 2022 7:56 pm

    Sound advice, my friend…LOL!

  16. Carol Parriott - December 30, 2022 8:07 pm

    I agree with Jamie and Linda’s ideas.  I would give her a small bouquet so it does not look too conspicuous.  And I would include a note saying he was interested in taking her out (maybe to lunch) which would be a short date.  If she responds great, if she does not it is her loss.  I can tell you for a fact there are some guys who may think they are out of a girl’s league in high school, but wait 20 or so years (which may sound like an eternity to a 15 year old) and see how that changes.  

  17. Linda Moon - December 30, 2022 8:40 pm

    I won’t tell you how pathetic I was was in Birmingham when I asked, then sort of scammed a teenage boy to go out with me. It was a LOL event, from what I recall. And loving someone…that leads us to the face of God, doesn’t it. So, love to you both Sean and Jamie, from me – Linda.

  18. Rhonda - January 3, 2023 3:31 am

    This made me laugh so hard- I could hardly manage to read it aloud to my hubs! 😂 Great abdominal workout and fine dose of HUMOR.


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