A love for someone older: romantic songs about falling for a senior or your boss.
There are many attractive things about older people—their reliability, the qualities you don’t have yourself, and a calmness you don’t often see in classmates.
Some of you might be in love with a senior at school, a boss at work, or even an older guy or woman who lives nearby.
So in this article, we’ll carefully select and introduce songs about falling in love with someone older from among countless love songs.
You might find the perfect song that matches your feelings.
Be sure to look for a favorite track!
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Love with someone older: Romance songs about falling for a senior or a boss (1–10)
Older boyfriendOku Hanako
Okahashi Hana’s “Toshiue no Kare” (Older Boyfriend) is a song that lays bare her straightforward feelings for an older man.
Its poignant lyrics look back on the time when her attempts to approach that calm, older boyfriend kept missing the mark, while also reflecting on herself now that she’s the same age he was then.
The line about how she couldn’t match him in anything except the strength of her feelings is especially heart-tugging.
Why not listen to this song and let it take you back to memories of your own older love?
I’ll fall in love now.HoneyWorks feat. Hatsune Miku
This is a song released in 2014 by the creator unit HoneyWorks, depicting a bittersweet romance.
He wasn’t my type at all—I was exasperated by how unreliable this upperclassman seemed—but before I knew it, I’d fallen for him…
When we think of upperclassmen, we tend to picture someone dependable and cool, but sometimes it’s kindness and gentleness that make your heart skip a beat, right? If you have feelings for a senior but can’t quite bring yourself to confess, this is a song you should definitely listen to!
To you, who are youngerSowelu
A collaborative number by Sowelu and Daichi Miura that sings about a romance between an older woman and a younger man, “Toshishita no Kimi ni.” It’s included on the 2010 album Love & I.
~Ren’ai Henreki~.
The song depicts a dynamic in which the younger man steadily takes the lead with a woman who’s timid about love, and as the song progresses, their love deepens more and more.
From the older person’s perspective, it’s easy to feel anxious or timid about dating someone younger, wondering, “Why are you treating me so well when I’m older?” or “Wouldn’t there be someone better for you?” But rather than overthinking it, sometimes it might be good to go along with your partner’s pace—just like in this song.
If you’re struggling with these worries, why not draw some courage from this track?
A love for someone older: love songs about falling for a senior or a boss (11–20)
Senpai.HONEY WORKS
Within that clear, cute voice, you can’t help but picture a younger girl.
The sweet, slightly clingy storytelling tone of the song fits right into the music scene from the late Heisei to Reiwa eras.
The lyrics are packed with junior-like lines such as “Would you accept someone younger?” and “Do you prefer long hair?” It feels like the song pushes past musical conventions and comes straight at you!
I want to be your lover.Abe Mao
Back in your school days, didn’t your seniors seem so much more mature precisely because you were fed up with your childish classmates? Some of you might have felt shy yet secretly harbored admiration or a crush.
A song that brings back those bittersweet student memories is Mao Abe’s “I Want to Be Your Girlfriend.” The dialogue in the lyrics is in polite speech, which suggests the feelings are directed toward someone older.
It’s a classic that captures the raw emotions of unrequited love.
We’re officially a couple!HoneyWorks feat. Hattori Juri (CV: Sakura Ayane)
HoneyWorks’ “We’re Officially Dating!” is a song that cheers on everyone who’s in love with an upperclassman.
Even while carrying their anxieties, the protagonist’s strength in taking that first step resonates straight to the listener’s heart.
The portrayal of the two growing closer little by little will make your heart race just by listening! Many will find themselves thinking, “I want to be like that, too.” Its upbeat, sparkling sound has the power to encourage love and give courage to those with a one-sided crush.
Give it a listen!
senpai snipertakayan
Takayan is a male YouTuber who’s popular for songs that capture women’s hearts.
“Senpai Sniper” is a track released in 2019, and it also drew attention because Takayan wore a girls’ school uniform.
The song candidly portrays a woman’s devoted feelings for a popular upperclassman, her aggressive side, and her possessiveness in wanting him all to herself.
It’s far from a typical love song, yet it strangely resonates—like, “yeah, that’s exactly how being in love feels.”