The answer kind of differs based on who that awkward person is. Try making them comfortable i guess by having one to one honest conversations. Perhaps talk about embarrassing situations together or do something with them that they love or generally feel confident about. I don't really know but this hope this works .
get to know their interests. But like not through a hollow conversation so you can check this off your list. Actually get to know your friend. Once you know what interests this person, like what truly moves their heart, it's only a matter of time for this person to open up to you freely. They would start to understand you truly care for them. It will be a lot easier for your friend to get outside his 'awkward' shell. Best of luck OP
Answers & Comments
First ask if they'd like to be loosened up. Just because you think someone else is a stick in the mud doesn't mean they'd not happy that way.
Loosen up how?? Just be yourself and encourage then to just be themself.
Loosen up, in what way?
Awkward about what?
The answer kind of differs based on who that awkward person is. Try making them comfortable i guess by having one to one honest conversations. Perhaps talk about embarrassing situations together or do something with them that they love or generally feel confident about. I don't really know but this hope this works .
It's not your job, just be yourself as you are without pretensions.
get to know their interests. But like not through a hollow conversation so you can check this off your list. Actually get to know your friend. Once you know what interests this person, like what truly moves their heart, it's only a matter of time for this person to open up to you freely. They would start to understand you truly care for them. It will be a lot easier for your friend to get outside his 'awkward' shell. Best of luck OP