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Absolutely. I was painfully awkward as an adolescent, but forced myself to be friends with cute girls and hang out with them. That got me used to interacting and joking with women, making flirting much easier.

My advice is to force yourself to do that which is limiting you. Exposure therapy makes future exposure easier as long as you aren't adjusting maladaptively with ruminative anxiety or panic attacks.

Check out the book "The Charisma Myth" by Olivia Fox Cabane. The premise of the book is Charisma is just another skill - something that can be learned and practiced, and is something the author coaches to C-level execs with a history of success.

There's a whole sub-culture around it: Pick-Up Artistry (PUA).