Re: interesting questions...i'mma say off the top it'd be pretty difficult to meet or see him without being out and about. the most logical place would be at a music event: concert, music festival, album signing, etc. i'm not sure what the intent of your meeting him is, but if it's just to tell him you appreciate his music, i wouldn't think it'd be too hard to do it at these spots...may have to wait around after the show a little bit, but still. if you're looking to see him on the street somewhere, i'd say check for city tour dates or be aware of when and where award shows or celebrity-filled events are: you can actually find them just mulling the streets and you never know who you can run into.
on the personal tip? i dunno...i mean, i'd love to get to know my favorite artists (Com is definitely in that group, if not at the top) on another level too, but i'd never wanna cross the line and invade personal space. our favorite artists are still people, we gotta remember that. i think it's wise you steered clear of contacting a close connect of his just to meet him. that shows respect, as well. if it's really important to you, though, just don't give up hope. and you're in Chicago, for pete's sake! lol, the odds are in your favor.
as for his selection in women?well... couldn't tell you that for definite, but he gives off vibes that an everyday woman is alrite with him. we have a chance! lol.
i've rambled quite a bit, lol. but i hope this helps.
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