For the first phase, choose Flirt, then Crass. She will stop talking with you. After a short time, speak with her again. When she agrees to speak with you, say something even more crass. She will express disgust, then turn and walk away.

For part two, simply navigate through all the options for whichever magazine one chooses.

If the Grifter succeeds in both phases, every member of the team gets this badge.