I can't send my friend a message

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I'm trying to send a song in a message to my friend, and It's just not having it. We have an ongoing conversation in my inbox already, and I tried pasting the link in there and clicking send. It looks like it works, but if I close and reopen Spotify it's no longer in our messages. And If I click "Share" then "send to" his name doesn't come up in the list on the desktop app, but it does in the web player app, interesting, but in neither can I send him the song.