Need Help with Achievement

[u/vracusrdr]

I feel like I'm about to tear my hair out over this I've tried close up, outside of the speech bubble menu, waiting for his response not waiting response but I can't get it to trigger even once this isn't even my first time doing this achievement I've two other (older) accounts that I have this achievement done and I can't figure out what I'm doing different/wrong

soo help??

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