The 10 Worst Fictional Relationships In Pop Song History (Male Singer Edition)

N.B: I had to make the executive decision to stick solely to male singers, not only because it meant I could delve deep into boy bands of days gone by, but because otherwise this would turn into the Kelly Clarkson happy hour really fast, and that is best saved for drunken karaoke with your best friend whose dude just took a page out of A.J. McLean’s playbook. Don’t know what I mean? Read on and reminisce.

‘Celebrity,’ by *N Sync

[youtube Five of the 13 songs on *N Sync’s Celebrity album are about break ups of one kind or another – and in all of these instances, it’s because the girl has been egregiously awful to our boys. (Is this a good time to ask how singing about one girl works when there’s five voices at play? Are we supposed to assume that it’s the lead singer confronting his paramour, and his buddies are just harmonizing Westside Story-style? Is this a polyamorous relationship? Is she awful to all five guys at once? I’ve been really confused about this since I was like, 9 years old, but I digress.) It’s kind of amazing how popular this song was, at a time juuuust before celebrity gossip really hit it big on the Internet, because you know that this could be considered mild shade at anyone who’s famous just for dating someone famous. I’d imagine that it’s got to be a tough life when you’re famous and you’re looking for love, though. How do you know when someone loves you, or when they just love your perks? Famous people need love, too! Paparazzi and millions of adoring fans and managers and agents and shiny statuettes can’t replace the warmth of someone who loves you for you, with or without the Twitter verification.

But to be fair, why wouldn’t you want to eat cheese like ev-er-y day? You can hardly call someone a gold digger because they are a dairy aficionado. I don’t know. I’m vegan. Maybe you can.

‘If You Left Him For Me,’ by Cody Simpson

[youtube It is very, very hard to speculate from one relationship to another, but as a somewhat well-adjusted single person who totally doesn’t spend half her sleeping time fighting with her cat for bed space, I think it’s pretty safe to say that advocating that someone leave their current relationship for you is an A+ way to ensure that eventually, they will probably leave you for someone else too. I think the kids these days call it karma.

‘Heartbeat,’ by Childish Gambino

[youtube You can listen to this song at least 100 times and find a new nuance to the ins and outs of this gray-area relationship with every single playback. From what I’ve ascertained, Gambino and the girl in question dated once but broke up because he’s a craptastic boyfriend; but now that she has a new boyfriend, he wants her back. On top of that, he Facebook-stalks her new guy, accuses her of letting cake go to her thighs, calls her crazy, but also admits that she’s great in bed and has a filthy mouth, so it’s six of one, half a dozen of the other, and all kinds of Lifetime movie epic.

‘Happily,’ by One Direction

[youtube So you’re sitting there, minding your own business, Spotify profile on private session, bopping along to a certain band, and you hear the following lyrics: “It’s 4 a.m. and I know that you’re with him. I wonder if he knows that I touched your skin. And if he feels my traces in your hair, I’m sorry, love, but I don’t really care.”

Wait, what? Not only are these boys who you feel borderline guilty about listening to in the first place a little stalkerish (4 a.m.? Really Harry? Really?) and Buffalo Billish (it puts the lotion on its skin, etc.) but they’re (he? Again with the one girl split five ways conundrum) basically imagining you with your boyfriend and mentally photoshopping their/his face(s) onto some poor dude’s mug. They/he want(s) him to know you’ve been unfaithful. They/he want(s) you to be found out. I bet they also think that if they/he dumps you, you’ll have no choice but to run into their/his arms. And then you’ll frolic off happily, as the song suggests, but really, can we nail down if this is one guy singing or five? I’d like to be able to stick to one pronoun, thanks.

‘Every Other Time,’ by LFO

[youtube Are you? Aren’t you? Are you hot? Cold? In? Out? Up? Do… okay, obvious Katy Perry precursors aside, sometimes you really just need to have The Talk with your love interest and A, decide what this whole thing is between the two of you, and B, maybe not do a donut on your kind-of-boyfriend’s lawn just because you’re mad at him? I don’t know. It’s probably in the best interest towards having a functional relationship. If you’re not interested in having a healthy love life, by all means, use this song as a blueprint. (Just maybe don’t compare yourselves to dolphins. That’s weird. Penguins are cute, and they mate for life. Stick to penguins.)

‘Lips Of An Angel,’ by Hinder

[youtube Both Rob Fee and Lance Pauker independently suggested this song as a d-bag anthem, and you know if it has two votes from upstanding gents such as themselves, it’s pretty solidly awful. I really don’t know what’s worse here: the fact that he’s trying to blame her by saying that she makes it hard for him be faithful; or the fact that he decided a short-sleeve shirt, vest, and tie were a cute look.

‘Tell Me, Tell Me… Baby,’ by *N Sync

[youtube Like I said, almost half of the songs on Celebrity are about really messed up relationships, so I’d be remiss to make this all but a survey of *N Sync’s greatest hits. But though ‘The Game Is Over’ has those really awesome digitized arcade effects, and ‘See Right Through You’ is ‘Celebrity: The Sequel’ in which the girlfriend of choice also likes to go to every Playboy Mansion party, this is a new low. The girl is a commitmentphobe. She refuses to sit down with Justin, JC, Joey, Chris, and Lance, and say, “Hey, okay, I want to date you. I want to be, like, Facebook official with you.” (And suddenly, Zuckerberg seems like a goddam genius for that ‘in a relationship’ button. If only Facebook came around a few years sooner, boy bands the world over could have avoided a ton of heartache.)

‘Gold Digger,’ by Kanye West feat. Jamie Foxx

[youtube Let’s take an inventory for the court, shall we: Four kids, including a baby by Busta Rhymes; a dalliance with Usher; letting Yeezy buy dinner for her and all her brood, and then leaving him to do the dishes when he can’t afford to pay for everyone; buying liposuction with child support money; a bigger car and house than her ex’s; and oh! that’s right — the kid isn’t even his*. I think that wins for worst girlfriend ever.

*Say what you will, but North West is totally Kanye’s baby. Those eyebrows do not lie.

‘The Call,’ by The Backstreet Boys

[youtube It’s very possible that there are two periods in a millennial’s life: B(t)C, when you are young and carefree and think this song is catchy as all heck; and A(t)C, when you realize that this song is about how the narrator is actively cheating on his girlfriend — and then walks us through the entire scuzzy affair, expecting to receive sympathy at his apparent remorse that his MAIN lady left him because she found out about the side chick. (Jee, you think?)

Anyway, in the name of good investigative journalism, I asked my mom how and why she let me listen to this song when I was all of 11 years old, and she could only shrug and tell me, “Well, I listened to ‘Why Don’t We Do It In The Road’ when I was that age,” so we’ve basically been letting kids listen to subject matter way beyond their years for decades now. No wonder our society is in the state it’s in.

‘Cry Me A River,’ by Justin Timberlake

[youtube Few public burns have been as classy or as catchy as this one. I love you, Britney, I really do. But I mean. Cheating on pop’s golden boy was probably the beginning of your downward spiral. And, sure, the video veers a little on the stalkery, lecherous side, but hey, a relationship is a two-way street. The whole thing was doomed from the start (or at least from those matching denim outfits onward, because I mean, come on.) Thought Catalog Logo Mark

Writer. Editor. Twitter-er. Instagrammer. Coffee drinker. (Okay, mostly that last one.)

Keep up with Ella on Twitter and

More From Thought Catalog