I remember the last thread. Never posted in it, though, probably because I couldn't think of any songs at the time to fit any pairing I like. But since a particular song's been on my mind lately, I think I found a pairing this could relate to.
Aoi Shiori (Blue Bookmark) - Galileo Galilei (the OP to Ano Hana)
I feel this fits the pairing of Wizardmon/Gatomon from Digimon, as through the point-of-view of Wizardmon. I don't exactly have a reason for why I feel it fits, but given how the two never seem to stay together without being separated, I suppose it can be seen as a way for Wizardmon to tell himself Gatomon has moved on, so he should let her go. The song's reminiscent and melancholy enough to work.
There's also a female singer in the song, so it can be somewhat of a duo where both of them are talking about moving on. But the part I'm posting is the beginning of the song, so the female singer is kind of a backing vocalist.
Nanpeeji mo tsuiyashite tsudzurareta bokura no kibun
Doushite ka ichigyou no kuuhaku wo umerarenai
Oshibana no shiori hasande kimi to korogasu tsukaisute no jitensha
Wasurekake no renga wo tsumiagete wa kuzushita
Ikooru e to hikizurarete iku kowai kurai ni aoi sora wo
Asobitsukareta bokura wa kitto omoidasu koto mo nai
Sou yatte ima wa boku no hou e oshitsukeru hizashi no taba
Mada futari wa sugu soko ni iru no ni "douka mata aemasu you ni" nante
Douka shiteru mitai
(Our feelings have been written down over countless pages,
But for some reason, I just can't fill in this one line of blank space.
I put in a pressed flower as a bookmark and roll along with you on the bike we found thrown away.
We piled up the bricks we've forgotten and then tore them back down.
We're being pulled to the same level, to be equals. All tired out from having fun
I'm sure that we won't remember the frighteningly blue sky.
In that way, a bundle of sunlight now pushes in my direction.
The two of you are still right there, but I find myself praying that we can meet again.
There must be something wrong with me.)