One can flirt with the Grim Reaper, and become WooHoo partners, but it will not complete the action beyond the excited dance at the idea of woohooing.
The woohoo action cycles and cycles, not clear...
Ideas
I've had the same problem with Grim. I figured out that I have to summon Grim by inviting him over with the social/friendship panel. I cannot summon him with the grimophone and then woohoo with him.
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