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Failed first time, should I approach it in a different way the second time?
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My roommate is a single male. (I am also male, single, divorced.) We hit it off so well. A few months ago, I asked him if we could be boyfriends. He said he was attracted to females. But he said how about a brother like relationship, as he always wanted a brother! I told him something like, β€œbut as brothers, you could move out and live some place else, away from me.” So I said no.

After that conversation, it was a little icy, or frosty between us. But recently he started to warm up again. We went out to dinner a few weeks ago. I felt that dinner was an absolute 10, just like all the times we went out together before! (All my dates were at most at 7 maybe.)

What should I do next? Oh, at dinner, he also told me that his parents wanted him to get married but he did not want to. And he decided not to go to his parents for the holidays because of that!

I am scared of doing another β€œtalk” and the same thing repeats (brother, not boyfriend). Any thoughts, suggestions, ideas as to what I should do, or what I can do in regards to the relationship?

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1 month ago