The Best of the Worst Relationship Advice in Pop Songs

image credit: Kristina Sczebel

Love is the drug of choice in pop music — really, all kinds of music. Past or present, we just can’t get enough of expressing romance and heartbreak through song.

Do older artists from previous generations have a more mature perspective on love? Are modern young singers just shells of humans when it comes to the romantic exploits they proclaim, or is there something more substantial?

Pop music says a lot. It’s not all incredibly shallow, hypersexualized, and glamorized, but a lot of it is. What are the songs really expressing about love, romance, and relationships?

Maybe we can learn something from how these pop songs deal with their relational woes. (Or maybe we’ll see that what they’re really saying is more troublesome when listening with a discerning ear.)

Listen to the Playlist!

Stream this playlist as you read! Or jump over to Spotify and stream the playlist.

[If rough language bothers you, some of this playlist might not agree with you. But the T. Swift songs provide unobjectionable territory (unless you’re allergic to catchy pop choruses).]

The Best of the Worst Relationship Advice in Pop Songs

When Your Relationship Gets Out Of Control

1. “I Don’t Trust Myself (with Loving You)” – John Mayer

I’m different than you think. I’m gonna work hard to get with you, then casually walk away from you, come back to you, then leave you. But hang on, because I will insinuate that you’re really the insecure one and I’ll try to appear to be caring, but I’ll still leave you to fend for yourself.

2. “Whatever You Like” – T.I.

Old dudes will tell women what they want to hear, but I am different. But not really, because I am an alcoholic spendaholic who will appease you so that we can continue a consensual physical relationship. I will patronize your intellect, but you will be fine with it, because we have a nice trade going: your body for my cash. Who cares about broke people anyway?

3. “Gold Digger (featuring Jamie Foxx)” – Kanye West

I am fairly certain this woman is chasing men for their money. I won’t say she is, but let me list multiple examples to demonstrate my case. She has a past, many children by various men, and requires extremely high maintenance, but I will still court her affection. And by affection I mean the assumed right to verbally trash her. Prenuptial agreements are highly advisable.

4. “What’s Luv? (featuring Ja-Rule & Ashanti)” – Fat Joe

I am very curious about your definition of love. I have very specific taste in women; namely, that they are physically attractive in these detailed ways. What does trust have to do with it? Let’s just skip the chatter and get busy, regardless of your current relationship and my insensitive, womanizing comments, and blatant disrespect toward you.

When Your Relationship Gets Needy

5. “Don’t Let Me Be The Last To Know” – Britney Spears

I heard you think I’m hot. But I need to hear it from you because I really like holding your attention. For real, just say it already. My feelings won’t be complete unless your feelings make me feel complete. I am honestly concerned that you will tell everyone in the world before you tell me, although we are already spending very personal time together.

6. “Genie in a Bottle” – Christina Aguilera

I am experiencing extreme amounts of sexual tension that you must help me solve. Allow me to use a Disney movie reference from the 1990s to illustrate. I am all about this as long as you do things my way. This will work out nicely, as long as we physically satisfy each other. You don’t seem to understand so I’ll continue to explain the genie illustration.

7. “I Knew You Were Trouble” – Taylor Swift

I fell for you even though you didn’t fall for me. This is what it means to be me, Taylor Swift. I will now wallow in self-pity and blame for our ruined relationship. I am so naive and self-sabotaging. How could I have missed that. Because you don’t really love me, you have probably never loved anyone or anything ever in your life, because if you couldn’t love me, you couldn’t love anything else.

8. “Before He Cheats” – Carrie Underwood

I assume many terrible things about my man, foremost of which is that he will wear bad cologne and teach billiards to a woman who does not drink whiskey. The most effective solution to my assumptions is to commit violent acts of vandalism against his vehicle rather than walking into the drinking establishment and talking to him in person. That will ensure he at least pauses when he continues this behavior that, in truth, I have not even verified apart from my own assumptions.

When Your Relationship Gets Really Painful

9. “Make You Feel My Love” – Adele

Your life sucks, but I love you. How do you feel about setting a world record for longest hug? We will probably die hugging, that’s how long we will hug. To prove my dedication to you, I will put myself through the excruciating physical torment of starvation. Seriously, I will do anything for you.

10. “All of Me” – John Legend

You are very confusing. Either that or I have contracted a serious case of vertigo. I will impress you with my poetic paradoxes. We would be so great together, I can hardly stand it.

11. “Heal Over” – KT Tunstall

You got hurt but I will hug you. Stop talking to yourself. You will probably fail but who cares. Life sucks. Stand very close to me. Let go. Hold on. Let go. Hold on. You’ll probably be OK eventually, but in the meantime I’m going to keep giving you conflicting advice.

12. “Skinny Love” – Bon Iver

What’s wrong with you? You seem pretty depressed. I will still get what I want from you, but I won’t try to make our relationship better. Why are you so lame? Hey, are we still good? Nevermind, don’t waste your love. I am sad. But I kind of like it.

When Your Relationship Is Failing

13. “I’m Gonna Be (500 Miles)” – The Proclaimers

We will do everything together, including but not limited to: waking up, going out, getting wasted, and talking absurdly. I plan to do a lot of walking to impress you. How much, you ask? 500 miles, of course. And then another 500 miles, after which I will collapse from exhaustion on your front porch to convince you that I am really committed to our relationship of waking up and getting drunk together.

14. “So Impossible” – Dashboard Confessional

Tell me everything about yourself, including your thoughts, generally specific, about: who you don’t like, how to act silly, what clothes you consider fashionable, if caffeine late in the day affects your circadian rhythm, and other sundry details. Maybe I will skip work to talk to you, or maybe I will set you up with my friend, but maybe I’ll set you up with myself. Is that awkward? I am admittedly self-defeating and awkward, but you like that, right?

15. “Some Fantastic” – Barenaked Ladies

I don’t kiss sick people. Let’s do mean stuff to animals then make out. I want to get with you. You cut my lip when we made out, so I’m sending you to space. But since you’re in orbit, I became self-loathing and will do anything humiliating to get you back, like wear t-shirts. Plz?

16. “The Blower’s Daughter” – Damien Rice

I have an easy life. I am looking at you. Still staring. Why is your dad’s occupation relevant? It’s windy here but I don’t notice because my gaze is locked on you. I think you’re the worst. But I’ll still stare at you. Ah, screw it. I’ll find someone else.

17. “When I Was Your Man” – Bruno Mars

I royally screwed up. What was I thinking? I didn’t do all of the obvious things that everyone does in a happy relationship, including dancing, hand holding, and giving attention and flowers. Now you’re with another dude and I am sad/pissed. Since I was too late to do anything decent and normal in our failed relationship, I hope your new guy does. I loathe myself.


What other pop songs have great or terrible relationship advice? Answer in the comments below.


If you haven’t seen it yet, check out this post that was picked up by my friends at Made For More:
Why I Turned Off My iPhone Notifications & You Should Too


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