When Valentine's Day rolls around, it's natural to daydream about winning someone over with a perfect collection of songs that encapsulate your feelings, represent you as a person, and speak to your potential as a thoughtful lover.

Don't do it.

In reality, creating a mixtape with the goal of sparking romance is akin to attempting to yank Excalibur from the stone. It might work for someone out there, but most of us will just wind up with crushed dreams and chaffed palms.

If, however, you're insistent upon braving the classic one-two punch of embarrassment and awkwardness, you should at least follow my tips to lessen the impact of your very bad decision. How am I qualified to hand out mixtape advice? I lived through the worst case scenario.

My first job was bagging groceries and rounding up stray shopping carts in the local supermarket. I was in love with a cashier. She was in college, I was just wrapping up high school. She was funny, smart, and liked the same stupid things I did. Her auburn hair was cut in a bob, tucked back with a little bow clip. Her eyes actually sparkled. Looking back, I suppose she had a severe ocular disease, but at the time it cemented her spot as the most beautiful girl in the world.

I would ignore cashiers with long lines of people buying 300+ cans of potted meat, bagging groceries for this girl while she worked the 10-items-or-fewer lane. My shopping cart duties were sorely neglected, to the point that a roving pack of post-apocalyptic punks outfitted the abandoned carts with spikes and terrorized the parking lot with a blend of gladiatorial combat and demolition derby.

My approach to seducing women was just as smooth and understated as it is now. I would hint at my attraction in extremely subtle ways, such as being very quiet and polite, and not revealing how I felt in any way. For some reason, this wasn't working, so I decided to make a mixtape and hand it to her on the last day before a two-week Christmas vacation.

It was a genuine cassette tape. I probably wrote something that I thought to be clever and endearing on the label, like a quote from Scud: The Disposable Assassin. The song selection was all over the place. There was, of course, "Nightswimming" by R.E.M.:

There were several Otis Redding song, including "Tramp," because just listen to how good that song is. Then came the pièce de résistance, the finale: a cover of "Why Can't We Be Friends" by Smashmouth.

It was a great mixed-message tape. Christmas was looming, so I covered it in red wrapping paper spotted with little cartoon Christmas trees. Romance.

The handoff went as smoothly as you'd imagine. I waited until I had clocked out for the day, almost talked myself out of going through with it, then pressed the tape into her hands with a nervous smile while mumbling some sort of apology.

How did it work? Two weeks later, when I returned from my vacation, she was dead. It was the shopping cart apocalypse punks.

Okay, I made that up. Instead, she treated me very kindly, never brought up the tape, and from that day forward regarded me with an expression saved for someone trying to figure out a puzzle made of rabies.

If you don't think I'm qualified to warn people what not to do, you stopped reading when common sense kicked in, somewhere around the third paragraph. For everyone that's left, these are three simple guidelines for making your terrible Valentine's Day mixtape not so terrible.

Picking The Right Songs

Stay on target. Don't follow "Nights In White Satin" with "Break Stuff." In fact, don't follow anything with "Break Stuff". I hate you so much. Stick to songs that either musically or lyrically fit into a theme that goes beyond Songs You Like.

Once you narrow your selections down, give everything a listen with a fresh ear. Sure, you might get a romantic vibe from The Toadies' "Tyler," but it's probably a good idea to go over it again and listen closer.


There's no need to gussy things up. This is a simple and pure gesture, an invitation to your heart. Don't cover it up with Christmas-themed wrapping paper. Just smear some chocolate on it, because chocolate is romantic.

Actually, do you have access to some flowers? It wouldn't be a bad idea to get a pair of scissors, then (very carefully) use those scissors to cut a hand turkey out of a piece of construction paper while you sit near those flowers. Hand turkeys are known to stir the loins like no other aphrodisiac.

The Giving

Approach your love interest with confidence, but not too much confidence. Keep stepping forward. Don't crabwalk to the side - you don't have the peripheral vision for that. Stop walking when you're close enough to reach out and touch them with a fully extended arm, not when you can just barely see them on the horizon.

Now comes the moment of truth. Casually mention that you put together a few songs, and that you hope they like them. DON'T let on the fact that you spent the better part of three weeks getting the mixtape just right, and that you had to read an article on the internet to avoid fucking up!

Hand it over. Smile. Without sounding as eager as you truly are, ask them to let you know what they think. Now walk away.

There, it's done. If you did everything perfectly, the object of your desire will wait until you're out of earshot before laughing.

– Dennis "Corin Tucker's Stalker" Farrell (@DennisFarrell)

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