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1)What are your initial thoughts on this as a way of proposing? I fear it would come off as more cheesy than romantic?
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I didn't think I'd hear from him, but later, he invited me to join him at the other bar. We ended up having a very fun night, talking with his friends and generally carrying on. He was still a bit shy/awkward, but throughout the evening, he got a bit more comfortable. Towards the end of the night, someone asked, "what's everyone doing tomorrow," and I said I was going to my friend's comedy show, and the guy I like said, "oh I'll go to that, send me the details."
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