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”I Guess” describes the experience of taking someone home after a night out.

In the live performance of the song, she first teaches the audience the melody of the bridge so they can sing along at the end of the song. When the music calms down toward the end, she also plays three notes on the piano with Kelly, her guitarist.

On March 7, 2024, McAlpine hinted at the announcement of this song’s release by sharing a reel of her playing it on tour, with the caption “i have more to tell u tmrw….” The next day, she announced the release of the song. This song is now the second single from her third album Older, following the release of the title track.

There seems to be a pattern of releasing these singles on the 13th day of each month. Thirteen has previously been mentioned as McAlpine’s favorite number, and the thirteenth track of each album is always about her late father who passed away on the 13th of March, 2020.

McAlpine went on to release a statement on Instagram when the track released:

"“I Guess” is out now! i love this song so much, i hope you do too.

thank u to @ryanlerman @masonstoops & @alrightsettledown for producing this song with me, ryan + jeremy for helping to write the ending melody & all of the crazy talented musicians all over this track! (@mooserob @carm_band @sterloid @libramento @taylormackall ) also special shoutout to the toronto crowd of my last tour, i took your “ohs” and added them to the outro :‘)

@sarloson thanks for mixing u killed that & @davekutchnyc thank u for mastering like a pro"

"I wanted to put it out today ‘cause today is the four year anniversary of losing my dad, and I just thought that it would be a good way to honor that."

— via YouTube

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