You got to be direct generally. I'm a pretty stoic person myself and I generally prefer when people are direct with me about their feelings. Just ask him how he feels about being in relationships, then you'll know how he feels. Its better to know then to wonder.
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wow that kinda sounds like me but not sure how to answer your question he is the way he is for a reason
I think you need to be verbal with him. He may have had it rough in his life, generally there is a good reason why people would be stoic. The fact he is hanging out with you must suggest he feels comfortable around you.
I would find a more open guy to be in a relationship with. He's not gonna give you what you need and he won't get any better
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Since most people don't understand stoicism, I'll give you this: not showing emotion and not feeling emotion are two very different things and stoics don't show emotion 98% of the time.
get him drunk , most people i know will be totally open their heart when they are drunk , especially tequilla
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