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how to talk to hana after buying her a bikini?

You need to invite her to the beach using Eros' PC, in his room.

I'm also getting stuck here. Every time I try to invite her to the beach I get the response "I'm working right now, stupid." Can you not advance Hana until you have a 2nd girl to work the cantina? If so, how do I unlock more girls? Every time I go to the lab the only option I get is "back". Am I missing something?

Make sure Hana is not locked working in the canteen in the daytime. You have to advance in Hana's level so Lily can give you the quest to send Hana to her world and/or bring Kaisa from  hers.