Dunno if you've already tried it, but singing karaoke at bars/clubs matches with your longer-term goals. It will also get you used to stepping outside your social comfort zone (it's soooo much easier to just sit and watch other people act like fools rather than risk derision yourself!), performing in front of crowds (a social skill unto itself), gets you out meeting people, and gives other people an excuse to talk to you! If you're paralyzingly uncomfortable singing alone to begin with, you can sing duets or in groups.
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