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If you are ready, listen to what everyone else here is saying. Make sure you are ready though, you seem worried about that part. He will deal with his brothers if that would even be an issue. I've dated guys in two houses, and stayed the night with them, and it was no big deal. Granted with the first guy, I wouldn't walk into Sig Chi alone for like three months. (I was a big fan of the hoodie.) The reality is that if you act naturally about it, they won't blink an eye. Just really make sure you are ready to be there, that is most important, boys are dumb and will be fine. Besides, people are right, the strangest things happen at 2am in a fraternity house...it really can be quite the experience.
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