Does he stand there facing you or does he move around?
If he moves follow him and if he doesn't, move away from him and then walk back over.
Also, did you pre-build settlements before talking to him?
I had this problem when conqueror first released, I just had to keep close to Jammer while he walked around and eventually the dialogue option worked properly.
He should stay standing in front of you but because he's moving it's stopping the dialogue, same as if you walk away from an npc that opens dialogue with you.
Do you have a dialogue extender mod installed ?
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