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I would just avoid the topic of greek life and recruitment all together with this guy. It sounds like he has some things he needs to work through. If he brings it up, you can always diplomatically say something like "We have different opinions on this, and I want to check things out for myself, so let's just drop it" and talk about something else.
It's good that your boyfriend is very supportive. Mine wasn't and it was terribly difficult at the time because when I needed comfort, he reitterated all the reasons why I shouldn't go through recruitment. We broke up shortly after my new member period started.
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