Shoulda Never

Album

Single

Label

Atlantic Records

Genre

Trap Soul

Media Type

DD

Duration

3:06

Entered Chart

May 9, 2026

Peak Date

May 9, 2026

Released

April 24, 2026

"Shoulda Never" is a soulful track where Kehlani and Usher trade verses about the internal conflict of sleeping with a lover they know is bad for them. The "Shoulda Never" title trails off like the thought itself - too painful to finish. It feels grammatically unfinished because the thought itself never fully lands; it trails off mid-confession, mirroring the cyclical logic of toxic relationships and that state where every mistake is immediately followed by the conviction that things will somehow be different, despite overwhelming evidence to the contrary. Neither singer appears to be addressing a specific public ex. The song keeps its target deliberately vague, allowing both artists to inhabit parallel stories of failed resistance rather than narrating one shared romance. The song nods to Usher's 1998 hit "Nice & Slow" where he spells out his full name: "U-S-H-E-R, R-A-Y-M-O-N-D." In "Shoulda Never," Kehlani mirrors the move in her own verse: "They call me K-E-H-L-A-N-I," asserting equal status with her collaborator and paying homage to his classic. Kehlani wrote the song with Babyface, Khris Riddick-Tynes, and Dixson. Production was helmed by Babyface and Khris Riddick-Tynes. The legendary R&B hitmaker Babyface (Kenneth Edmonds) is responsible for classics for Boyz II Men, TLC, Whitney Houston, and many others. Khris Riddick-Tynes is one half of the production duo the Rascals alongside Leon Thomas III. Georgia songwriter and producer Darius Scott Dixson, also known as Dixson, is best known for his Beyoncé collaborations. Both Riddick-Tynes and Dixson helped Kehlani craft her hit song "Folded." There was a previous Usher collab that Kehlani accidentally revealed during an Apple Music Radio interview before it was ready. She told Vibe Usher FaceTimed her immediately and admitted frankly, "I don't like the song." Rather than a rejection, Kehlani saw it as an act of mentorship. Usher explained to her: "I really believe in you as an artist... this is me saying, let's keep pushing and let's keep writing until we find the right song." The two went back and forth over multiple sessions and song submissions before landing on "Shoulda Never." Speaking to Jack Saunders on BBC Radio 1, Kehlani described the excitement of matching Usher's trademark conversational flow: "Usher did his classic Usher baby rap, and I got to follow it up in his footsteps and pay my homage to him in that way." She also cited Usher's Confessions album as a major influence on her own storytelling instincts, calling it "one of the best R&B albums of all time." "Shoulda Never" is track 8 on Kehlani's 19-track self-titled album. It's a great example of how the album mines '90s and early-2000s R&B sounds, updated with Kehlani's signature emotional frankness.

Should've never
Should've never
Should've never

I tried to tell myself you're never gonna get it again
Laying here next to you, not what I intended again
How did you crack the code (code)
When don't nobody know (know)
How to get me in position?

I thought I blocked your ass, you found another way to get in
Screw all my inner thoughts, I'm thinking 'bout us getting it in
On every countertop (top)
I'm yelling, "Please, don't stop"
And you know where it's going

If somebody told me this was it (ooh)
That you was on some different shit (oh-ooh)
I would've made a decision that was better than this
Instead of wasting my time

I tried to stop myself in time (should've never did it)
I did it anyway, I probably should've never hit it

When I knew better, but I didn't do no better
I just wasted my time (yeah)

Don't get it twisted, I ain't never been no regular type
I'm not so into you that I'm gon' let my good years go by (goodbye)
Just 'cause you laid it down and knocked it out like dominoes
That don't give you no permission
To fuck me over when you know that I been fuckin' you good
Why pull me in to push me out just 'cause you know that you could?
That's how I end up in and slip and fall in love again
Right back in love (oh), same position

If somebody told me this was it (then I)
That you was on some different shit (wish somebody told me, I)
I would've made a decision that was better than this
Instead of wasting my time

I tried to stop myself in time (oh, I did it anyway)
I did it anyway, I probably should've never hit it
When I knew better, but I didn't do no better
I was wasting my time

Okay, K, USHER, baby, look

Every time that I tell myself that I'm probably gonna let you go (I, I, I)
I get one foot out the door, then you come and pull me back for more
You know I
Can't resist you, that's my issue
Forget the shit we been through
'Cause you always put it down for me
Make it disappear like alchemy

They call me K-E (K-E) H-L-A-N-I (N-I)
Nini with the ill nana (oh, yeah)
Tsunami, take you under (whoa)
This body hit like thunder (thunder)
This ain't no one-hit-wonder (no)
Here's another, oh
'Cause I'm rare like a Mona Lis'
You should treat me like a masterpiece, I (okay, K, baby)

Tried to stop myself in time (yeah, should've never did it)
I did it anyway, I probably should've never hit it
When I knew better, but I didn't do no better
I was wasting my time

If somebody told me this was it (I would never believe it)

That you was on some different shit (ooh)
I would've made a decision that was better than this
Instead of wasting my time