I have had only two chat experiences, one at this forum and one other and my interest was primarily in Mal's trivia games.

I feel uncomfortable in chat because it usually means dropping into the middle of a conversation and intruding myself. Flirting would be the last thing on my mind.
My first attempts at internet flirtation have been at Moe's, and only then because it seemed to be part of the theme for that forum. I flirt outrageously there, not for an ego boost, but for the sense of inclusion. I've never felt I had to qualify that this is just fun for me because who would take someone 20-30 years older than themself seriously? Occasionally, I get invited to join in a sexually themed tableaux by Tec but I keep my participation in those to that of a "stage hand." Quite honestly, I wouldn't know the first thing about anything more than the harmless flirt.