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Valentines Day — A Cautionary Tale

If there’s one holiday loaded with pitfalls, sand traps and quicksand, it is most certainly Valentine’s Day. A day filled with the…

John glavin · 2026-05-15 15:13 · 20 claps · 7.4 min read paywalled
#humor #the-south #dating-advice #valentines-day
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Wiki topics: 💑 · Relationships 😂 · Humor & Satire

Valentines Day — A Cautionary Tale

This is an excerpt from my Substack “A Carpetbagger In The South

This is an excerpt from my Substack “A Carpetbagger In The South

If there’s one holiday loaded with pitfalls, sand traps and quicksand, it is most certainly Valentine’s Day. A day filled with the potential for miscommunication, wildly differing expectations — and if you’re inexperienced enough (many would say STUPID enough) to set up a first date for Valentine’s Day…well, you’d be guaranteed more fun putting a smelly burlap sack over your head and wandering through a mine field on the Ukrainian/Russian border…with both sides taking Vodka-fueled potshots at you.

So when young Aggie Laggert sauntered confidently down the road from his job at LK Pick Your Part Auto Salvage just up the road on the other side of the interstate and into Vi’s, he had an uncharacteristic spring in his step.

Somebody had ‘Her Strut’ by Bob Seger on the jukebox, and by his second stride Aggie laughed out loud and managed to get into perfect step with Bob, even though Aggie’s terminal caucasianality once prompted Jimmy Don to comment with disgust, “That boy couldn’t find the beat with both hands and a Geiger counter.”

Aggie continued his strutting to the bar, where he asked Vi for a beer…AND a glass. Jimmy Don, Edzel Timmons and Augie Tanner stopped their conversation and slowly turned as if expecting to see a unicorn.

“A GLASS? What the hell’s gotten into you, boy?” quizzed Jimmy Don. “Make sure when you take a dainty sip you hold out your pinky. Otherwise Vi’s gonna order you thrown out.”

Vi placed a long neck of Natty Light and a frosted glass in front of the grinning young man, and nodded. “That’s puttin’ lipstick on a pig, Aggie.”

Waitress Any Simpkins sauntered over to Vi with an order. “’Sup, Ag? You win the lottery?”

Edzel shook his head. “That or he has a date…” Aggie blushed as Cyril Davis, normally the target of patrons’ teasing, chanted, “Aggie’s gotta date! Aggie’s gotta date!”

Cyril relaxed a bit since the bullseye was for once on someone else’s back. “So,” baited Cyril, “what’s HIS name?” He guffawed as the rest of the bar tittered.

Aggie nodded and bowed. “It’s true. Gotta date. The FINE young parts rep from Delco…”

Doc Keller, having quietly taken a stool on the other side of the bar, nodded in agreement. “Ouch! A young lady who knows about CARS! Well played young Mr. Laggert.”

Aggie tipped his beer to Doc. “I’ve been flirting with her for months, and I asked her out a few weeks ago. Thought I got shot down — she said she had her kid that weekend. But she came in this afternoon and, FIRST thing she was like, ‘Aggie! My little girl’s at her father’s next weekend!’ So, dear friends, we’re going out next Saturday night.” He took a pull on his beer and beamed like the perfect fool he was about to be called out for.

Amy stopped by the bar and froze. “Ag — wait. NEXT Saturday night?” Aggie nodded, and there was a collective groan from the patrons. Aggie was puzzled. “What’s the deal?”

Edzel shook his head sadly and called for Vi. “Darlin’, I hate to do this, but you need to shut down this establishment, and I mean NOW. We got ourselves a four alarm fire, and I intend to save our young but foolish friend here.”

Vi smirked and waved him away. “Leave the kid alone, Ed.”

Doc Keller shook his head. “I dunno, Vi. This has disaster written all over it.”

Aggie spoke up. “What the hell’s the big deal?”

Jimmy Don, who had the stool next to Augie, gently wrapped the kid from behind, knocking off his ball cap. “Hey, Valentino. Next Saturday is VALENTINE’S Day.”

“So?”

Another general groan from the attending bar flies. “My GOD, son. Valentine’s Day is a damn MINE field, even if you’ve been happily married for 20 years! What makes you think you can pull it off on the first date?” gasped Jimmy Don.

“Jimmy Don’s right. I hear even Jimmy and Rosalyn Carter almost divorced after Valentine’s Day once,” declared Edzel. “And I think they even shared the same wheelchair the last ten years they were breathin’.”

“It’s just another day!” exclaimed Aggie, waving them away. “You lonely old farts are just losers who don’t want to see my generation happy.” He motioned for another beer and shook his head.

“Oh, now he’s just an arrogant little wet-behind-the-ears punk,” Jimmy Don spat. He picked up his beer and retreated to the other side of the bar next to Doc.

Doc smiled. “Aggie, I know this is a rough bunch when it comes to love, but they’ve also been through the wars –“ Jimmy Don, mouth full of beer, pointed to Doc and then to Aggie in agreement.

Edzel raised his hands to Aggie. “Look kid, a first date on the supposedly most romantic day of the year? You REALLY want that kind of pressure?” Aggie shrugged his shoulders. “Okay, let me ask you — what were you considering doing on this first date?”

Aggie sat up and smiled. “Tullahoma Arts Center on Jackson’s throwing a wine and cheese tasting benefit — I thought that’d be both romantic AND worldly,” he proudly announced, looking around the room for support.

There was a sudden intake of breath. The jukebox went silent. And then as if on cue the entire bar exploded in convulsive laughter. Aggie for the second time that afternoon reddened — but this time in anger.

Jimmy Don fell off his stool and lay on the bar floor, holding his belly and huffing beer out of his nose. Edzel raced over, laughing, and pretended to perform chest compressions on the suffering man.

Doc, attempting to maintain decorum, put both hands over his head and placed his forehead on the bar.

Vi kept having to wipe her eyes, and Jimmy Jay, Jimmy Don’s son walked in, spied his father lying prostrate on the floor, and shook his head. “Jesus, Dad, it’s only 5:30. And you always say I can’t pace myself.”

Aggie briefly considered just leaving, but Augie Tanner, the youngest member of the regulars, patted Aggie’s back. “Aggie, correct me if I’m wrong, but the only thing you know about wine is it’s in the part of the liquor store you always avoid!”

Jimmy Don had recovered sufficiently to sit up. He was hiccupping, and managed to spit out, “Aggie, you better hope they’re serving a nicely aged can of Cheese Wiz!” Then he fell back on the floor, lost in laughter.

Doc Keller managed to control his laughter and stood up. “Aggie, here’s the point: there are TWO big BIG pitfalls you’re setting yourself up for.”

Aggie stared into his glass, angry but listening. Vi patted his arm. “Son, you run the very real risk of showing your date that you know absolutely NOTHING about wine OR cheese –“

Jimmy Don, still on his back: “Except you know how to CUT it –“

Vi pitched her dirty dish rag over the bar, aiming for Jimmy Don’s face on the floor. “And, if you manage to hide that you hate wine and the only cheese you like is Velveeta, you have then set yourself up for wildly unrealistic expectations on the part of Miss Delco.”

Aggie looked up at Vi and was clearly puzzled. Jimmy Don filled in his son on the bar’s attempt to save Aggie from himself, and Jimmy Jay rounded the bar, then sat next to the moon-struck lover. “Sorry, broh. I know you pretty damn well, and, look, no offense, but I just think you don’t have the nads to pull that off.” He slapped his buddy’s back and waved for a beer from Vi.

From the bar floor: “Jimmy Jay, make up some wine bottle flash cards for him. (in a sing song voice) ‘What’s this one, Aggie? Right! A Chevrolet Nouveau!’”

“You pull that off and all you do is land yourself in dating quicksand.” Jimmy Jay shook as if a cold draft had come through the door. “Wine and Cheese first. Next thing she’s gonna want you to go to her kid’s piano recital. THEN it’ll be the friggin’ OPERA! It’s a horror show I tell ya.”

Augie Tanner nodded sagely. “It’s dating froo paws like that that chicks’ll use against you as part of the bondages of holy matrimony.”

Aggie shook his head. “She’s not like that, guys.”

Amy Simpkins had parked at the bar for a break earlier. “Aggie, you know me.”

Cyril whooped. “Hell, Amy who HASN’T known you?”

Amy rolled her eyes. “Normally I’d side with the girls on this, but I like you, kid. I’d follow the advice of Jack Sparrow. ‘Take what you can. Give NOTHING back.’” With that, she picked up her servers tray and wandered over to the table of car salesmen she’d been entertaining.

Vi waved Amy away and motioned Aggie over. “Never mind her. Her theme song is ‘Love Is a Battlefield’. Look, I DO think it’s good to be open to trying new things —

Jimmy Don, still on the floor: “Yeah, like wine in a box…”

Vi continued, “ — you’ll never know if you’ll enjoy it til you try it. BUT –“ She pointed directly at Aggie. “NOT on a first date, and certainly NOT on a Valentine’s Day first date.”

Edzel looked philosophically at Aggie, steepled his hands, and leaned back — stopping himself because he realized he was on a bar stool and not an office chair. “Ag, why can’t you postpone the date? I mean, call her tomorrow, let her know, you know, you have to work, or wash your mother’s hair, get an appendectomy, something like that, but then RESCHEDULE for after Valentine’s Day? That way the pressure’s off!” He looked around the bar for agreement.

Doc nodded. “You know, Aggie, that’s actually a really good idea. If you want a real chance to make this work, give yourself every chance.”

From behind Doc, on the floor: “Yeah, like regular grooming.”

Aggie looked thoughtful. Augie patted him on the back. “Dude, you have literally hundreds of years of dating and marriage failure surrounding you right now. Take advantage of their wisdom. This is like your Relationship Brainstrust.”

Cyril piped up. “My uncle always told me he NEVER began a serious new relationship between December and February. ‘Better hook-ups than break-ups’ was his motto. After Valentine’s Day, hit the dating scene. By fall you can narrow the pack down to one for college football season. If she resents college football, dump her before Thanksgiving — no awkward introductions and holiday meals with family. And my uncle should know. He’s been married six times.”

Edzel nodded. “Wise words worth following.” Then he leaned forward and spoke quietly, confidentially as Jimmy Don finally regained his feet. “Remember. As a last resort, your right hand IS your right hand man.”

Vi careened around the bar and chased a laughing Edzel out the front door. Everyone guffawed, and Aggie looked relaxed for the first time since the beginning of the conversation.

Jimmy Don took a pull off his beer, then, motioning to Aggie, poured a bit on his right hand, exclaiming, “Hot damn — I’m gettin’ lucky tonight!”

The crew at Vi’s is featured in my next book — Vi’s Tavern: Rednecks, Longnecks, and Why It All Went South. Look for it on Amazon in June.


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