Re: Did I mess up?
You have to admit it was probably very awkward for your friend for the first time, I've always felt like you have to try it at least three times before the awkwardness goes away. (*as long as there is communication etc...) If you do decide not to try it again then let him know that it's alright and it was fun!
Definitely talk about it with all three of you present and just remember in five years you will look back on it and laugh!
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