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The Flyover Podcast – Valentine’s Day (Transcript)

(Opening Theme)

Welcome to a very special Valentine’s Day edition of The Flyover Podcast. Yes, Valentine’s Day, that most Hallmark of all the fictitious holidays! 

But, if you’re looking for a dozen red roses and a candlelit dinner next to the fireplace, well my friends, you may have come to the wrong place.

Because we’re going to start in the darkness on the edge of town, where the shadows of love cease to exist. We’ll get to all that lovey dovey stuff, don’t you worry, but like true love itself, you’re gonna have to work for it.

Let’s start at the beginning, nearly a century ago, on Valentine’s Day 1929, right here in Chicago.

At 10:30 that morning, seven North Side gang members were murdered just two miles south of Wrigley Field in Lincoln Park. They were lined up by four men, two of whom were dressed as police officers, inside a garage on Clark Street and shot with Tommy guns. The two fake police officers led the other two men, who were dressed in suits, out of the garage with their hands up, to try and give the appearance that everything was under control.

Of course, it wasn’t. This was a gangland execution in the heart of Chicago, believed to be the handiwork of Al Capone in his attempt to control the entire city’s bootlegging operations during Prohibition.

88 years later, another Italian guy with Jersey roots would record a song using the incident as inspiration, and a metaphor, for love and heartbreak.

Here’s Little Steven Van Zandt, aka Silvio Dante, with the “Saint Valentine’s Day Massacre.”

(Little Steven – Saint Valentine’s Day Massacre)

For those who remain hopeless in love, Valentine’s Day can be one of the loneliest nights of the year, a depressing evening of solitude among the beating hearts of blissful lovers. If you find yourself alone on the streets of the city that night, it can simply become too much to bear.

“I’m just so lonely,” a friend in New York once said to me. “I just want to be with someone.” 

And, you try to feel for him, y’know? You empathize. Or, at least, you try to empathize. You know, if you had the ability to have human emotions. Like The Terminator, I know now why he cries, but it is something I could never do. 

So you say to him, you say, you say something that you would have hated to hear back when the shoe was on the other foot. You say, “Hey man, I get it, but it’ll happen when it happens. You’ve got a great job, a ton of friends, you get to travel. Hey, there’s more to life than being in a relationship.”

“Oh sure,” he said. “That’s easy for you to say, you’re married!” 

And he’s right. I am married. And what that means, of course, is that we just got done arguing for 37 minutes about what kind of toppings we wanted on our pizza. So, yea, it’s a real paradise over here, lemme tell ya.

But, that splendid isolation is one of the reasons I’ve always loved New York City, particularly at night. Even if you’re the only one on the street, you still seem to feel connected – you’re never too far from an open bar or another lonely wanderer. You can’t help but embrace its unique solitude, basking in its beauty, and breathing in that intoxicating mix of excitement and sorrow.  

These next two songs truly capture that feeling. The first is Frank Sinatra’s “In the Wee Small Hours of the Morning,” from his incredible album of the same name. The singer is alone, either walking the streets or looking down upon them from his tenement window, still hanging onto hope that his lover might call. It’s a desperate plea, no doubt, but it’s all he’s got.

The next song was written by me, yours truly, about as quickly as I’ve ever written anything in my life. I had just heard the line “those long and lonely nights” repeated over and over in another song, and immediately wrote them down. Inspired, I kept writing, trying to capture the moment just after Frank’s song ends, when that unrelenting desire for connection manifests itself in even more desperate ways.

Come take a winter night’s walk in Manhattan with me and Ol’ Blue Eyes.

(Frank Sinatra – In the Wee Small Hours of the Morning)

(Kyle Pucciarello – Lonely Night)

Valentine’s Day can also have a bit of a dark side, as these next three songs all illustrate.

Are you strung out on some face?

Hell, I know it ain’t mine

That’s what Paul Westerberg wants to know in the first of these songs, the co-conspirator in an unhealthy love affair gone wrong. 

If you were a pill

I’d take a handful at my will

And knock you back with something sweet and strong

If you haven’t been…well I was going to say lucky enough…to experience this kind of thunderstorm of love, you’ve at least seen it in a movie. That wild lover who makes you leave all sanity and reason behind – you’d follow her into the dark and well beyond. Like some beautiful tornado, she’ll grab a hold of you and tear you apart, only letting go when she’s ready to move onto some other unsuspecting victim. Your heart? Your soul? Just the carnage she leaves behind, a warning to all who dare-to-love in her wake.

“You ever love something so much it hurts?” asks Chase Lawrence, lead singer of our next band, COIN.

This is what comes after the storm, that moment of realization that, whatever just happened, whether it was lust or love, it’s over. She’s gone:

So you really wanna break my heart?

Keep me burning on the back light?

Hey, hey, get away from me

Yeah, I’m talking to myself in the mirror half asleep

Once your heart knows it’s over, well, now you’ve got to get your head to believe it.  You can picture the scene, can’t you. Standing in a tattered t-shirt and jeans in a dimly lit New York City apartment, talking himself into moving on.

But, he can’t. It’s Valentine’s Day, what better time for some misguided hope. The song ends in the most forlorn way imaginable, Lawrence repeating “take your time, I’ll be around” over and over and over, the sad misfortune of someone who just can’t quite move on.

And just when you thought this Valentine’s Day couldn’t get any darker, in walks Fiona Apple. This last song is pure poetry, Fiona comparing herself, and love, to a flower that was cut from its stem too soon:

I’m a tulip in a cup

I stand no chance of growing up

I’m resigned to sail on through

In the wake of tales of you

The narrator in this one has made it out of that New York apartment, she’s even dragged herself to a few first dates:

I made it to a dinner date

My teardrops seasoned every plate

I tried to dance but lost my nerve

I cramped up in the learning curve

But, that learning curve, that’s the thing isn’t it? We’ve all been there. Learning how to open up again, love again. It takes time. I’m not sure that’s what Tom Petty meant when he sang “the waiting is the hardest part,” but it’s never sounded truer than when trying to get over that long lost Valentine.

Let’s wallow down in the trenches of Valentine’s Day with The Replacements, COIN, and Fiona Apple, each of them with their own take on what the word “Valentine” means to them.

(The Replacements – Valentine)

(COIN – Valentine)

(Fiona Apple – Valentine)

Alright, we’ve survived the dark side of Valentine’s Day, let’s bring it up…just a little though. We’re still tender. We’re not ready, just yet, for the real thing.

Because Valentine’s Day can be a lot of pressure, especially when you’re first dating someone. 

Like New Year’s Eve, or a birthday, there’s a great deal of expectation and anticipation for the events of the evening. What will you get her? Where will you take her to dinner? What happens if you’re lucky enough to go back to her place?

Speaking of, I always thought the most impressive night of the week to get laid was a Monday, don’t you? Anyone can get laid on a Saturday, or Valentine’s Day. But a Monday night? That’s special. 

Though, as you’re about to hear, maybe not everyone makes out so well on Valentine’s Night.

Because back in 2007, my last semester of college, I found myself at the beginning of a new relationship with February 14th right around the corner. For a long, long time, I was a bit of a hopeless romantic. Especially at that point in my life, I only dated someone if there was truly a connection and I could immediately see some sort of a future. I was not someone who went out on a date just to do it. So, in my college-aged mind, there was a lot riding on making sure this was a perfect Valentine’s Day.

I had all the plans you make when you’re at that age: flowers; a really nice dinner; a movie. But, to my surprise, she didn’t want any of that. Don’t surprise me. Don’t make a big deal out of it. Let’s just do something low key.

But, it’s Valentine’s Day! I’ve got to take you out! We’ve got to do something special!

“Okay,” she said. “Why don’t we go to Applebee’s?”

And here, dear listeners, is where we pause. Applebee’s. For Valentine’s Day. Really? The place I used to go to with my friends every, single weekend because there was literally nothing else to do in our town, for Valentine’s Day? For romance.


“Well,” I said, after trying to appeal to her senses for a few minutes. “If that’s what you want.”

On Wednesday, when Valentine’s Day finally rolled around, a major snowstorm had hit New Jersey. We thought about postponing or doing something at my off-campus apartment, but my friend and his then-girlfriend were having their own Valentine’s Day dinner there already. And her roommates, three single yentas, were having some sort of Un-Valentine’s Day Party back at her place.

So, Applebee’s it was.

I remember driving in the snow, the first mistake of the evening. A trip that usually took about ten minutes clocked in at just under forty-five. At least once, she may have suggested turning around.

“Oh no. You wanted Applebee’s? You got it!”

Finally, like two mushers at the end of the Iditarod, we arrived at the frozen food oasis just outside of New Brunswick, NJ. I don’t have much memory of the dinner itself, a pleasant, yet uneventful meal of reheated meat and pasta. But, I do remember dessert. I remember dessert oh so well.

Back then, and I don’t know if they still have it, whenever I would go to Applebee’s, I would literally only order one thing. I almost never had an appetizer. Never had a meal. Instead, I would get the Blue Ribbon Brownie Sundae, a giant, and surprisingly delicious, warm brownie with vanilla ice cream and whipped topping. Probably every Friday or Saturday night for like four years, this was the go to.

So, when it came time for dessert, it was like a reflex. 

“And, will there be anything else?”


And you’re probably thinking, “You were on a Valentine’s Day date? You didn’t think to, y’know, ask your date what she wanted?”

Well, sure, I asked! She said something that wasn’t the Blue Ribbon Brownie Sundae, and I ignored her.

No, of course I asked her, and she said she wanted something chocolatey. Boom! Brownie. Chocolate.  What could be better?!

Turns out, literally anything else on the menu, because when the dessert arrived, and I started to dig in like a man who had been lost at sea for several weeks, she noticed something.

“Oh no, are those walnuts on the brownie?”

  • Yea ::eating noises:: They’re delicious.

“Well, I guess there won’t be any kissing tonight.”

  • Whaa…?

Yeah, you’ve probably already figured it out, she had a severe nut allergy. Even if I went home and washed my mouth out with Clorox Bleach, it would have been too much of a risk.

This quickly became the saddest brownie I had ever eaten, the true tragedy of the evening.

Now, we can get into a whole thing about why didn’t she say something before we ordered it or why didn’t I think to ask, but that would be taking away from the true punchline of the evening.

Because, after this ill-fated dinner, we went back to my apartment, and played some games and watched TV with my roommate and his now-wife. We were having a good time, and stayed awake for the Conan O’Brien show.

After the monologue, Conan did his yearly “Valentine’s Day Survival Guide” bit, showcasing the things not to do on February 14th.

And they saved the most devastating blow for last. Because the final bit was a hilarious song making fun of anyone who takes their Valentine’s Day date to, that’s right, Applebee’s.


Oh, and the relationship? It lasted two more weeks.

(Outkast – Happy Valentine’s Day)

(Amy Winehouse – Cupid)

Like everything else these past eleven months, Valentine’s Day won’t quite be the same as it has been in previous years. That romantic candlelit dinner in your favorite restaurant, it’s gonna have to wait until next year.

I’ve joked throughout the podcast about the false importance of Valentine’s Day, undoubtedly a conspiracy perpetrated by the greeting card and candy industries to get us to spend money. It’s the falseness of the day that bothers me, the forced nature of it, not necessarily the idea behind it.

Because, to quote Judd Hirsch in “Independence Day”:

“All you need is love. John Lennon. Smart man.”

It’s not just Valentine’s Day that can be difficult to get through on your own, it’s every day. Life is best when shared with someone to walk alongside of you, who makes each day a little better. Someone you bring out the best in, and who brings out the best in you.

Lucky for me, I have someone who does just that. And, hopefully I do that for her.

Earlier in the show, we listened to “Lonely Night,” one of those twisted sort-of love songs I was usually best at writing. I always had a ton of trouble writing the songs that John Lennon’s buddy Paul could write with such ease, or that Stevie Wonder seemed to be able to sing at will. Even this podcast, my god, for whatever reason when I mix creativity with love, it’s never purely bliss.

I managed to get close, though, just once, in a song I wrote for my wife called “By My Side.” 

When I get lost inside my mind

I turn to you and see

You always have that way of knowing

Exactly what I need

Like I said, I got close, a love song through the lens of a tortured soul. But, that was the best I could offer at the time, the purest distillation of what love seemed to mean. You’re there for me. I’m there for you. And hopefully, we can have a few smiles along the way.

You’ll always be

Right where you’ve always been

Standing right by my side

So, hold me close, say you’re forever mine, and tell me you’ll be my lonely Valentine.

We’ll be seein’ ya…

(Bruce Springsteen – Valentine’s Day)

(Closing Theme)

The Flyover Podcast is recorded and produced by Kyle Pucciarello in Chicago, Illinois. For more information, please visit, @official_flyover on Instagram, or email us at

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