Private message crush outside group chat?

ishplump
I want to one how I can privately message this guy within my circle of friends, that's also party of a group chat we in without coming off as awkard. I only normally PM him for specific things or help with a trivial task. I just want to start asking how his day went and so on through PM. I can do it in the group chat but one it be for everyone and two he constantly keep it mute. (Also we been heavily flirting with each other when we hang out as in recently)
Private message crush outside group chat?
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