Sign up or log in to share. Hey, I would put Emily's mind at ease and go out with her. It's what you want and it's what she wants. I wouldn't worry to much about her being your best friend's sister because he's cool with it. But, I'd have a convo with him letting him know how you feel about her and telling him your intentions on going out with her.
We had a mutual break up after a few months and remained close afterwards. In college, my now wife and I decided to take our friendship to the next level. We were married a few years later and now have two kids. There is no awkwardness between any of us and the three of us frequently go out to dinner together. Everyone is lighthearted about it and my wife makes jokes all the time.
Every time that person enters the room, your heart starts to beat just a little faster. What if your crush is reciprocating your feelings? You could be creating an awkward situation between the two friends by changing the relationship dynamic between the two of you.
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