Would you go somewhere that will make you feel uncomfortable just for one person?

So I've been hanging with this guy a lot, he knows I have a crush on him and he still wants to hang out with me, like literally all night. One time it was so late, I ended up staying at his house because it was 4 am when we finally saw what time it was. So one of my friends won 4 tickets to a resort she invited me and told me to invite my friend, so I told her I will see, at first he said no because he doesn't know them that well ( we all work together by the way just in different areas, he works in at the warehouse, my friend and I work at the store ) which I thought totally understandable, I don't go anywhere that will make me uncomfortable either. So when he asked if I was still going I said yes because I always wanted to go but it's so expensive. Now he's saying he wants to go, I'm really hoping he's not doing this for me, because now I just feel bad.

Would you go somewhere that will make you feel uncomfortable just for one person?
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