yes it's weird, yes he could still like you, yes I don't get it either
i know 3 other couples that are like this 2 of which are now married. for some reason the guys can't go out with "there" girl on there own. as far as I've been able to pry out of them its something of a confidence issue. some feel more confident having there friends around or being seen with there significant other by people they know, others do it because they feel the time will go smoother then.
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maybe he thinks of you as a friend... why don't you tell him to not bring his friend that simple.
It sounds like he's trying to set you up with his friend. Sorry.
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he just isn't confident enough to be alone with you so he needs his "pack" he seems to have that kinda of mind especially if he feels "out matched" meaning since he is shy and younger he feels you got him by his cojones, so make him feel like you don't like for example stop teasing the poor dude its just reminding him of that
maybe he is bi... lol but if he isn't then he probably just has really low self confidence and doesn't know what to do when its just him and his friend is constantly giving him advise. tell him that you two need to have a date alone and see how he reacts.
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