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I have progressed a large amount of the story now but didn't know I needed to meet the tailor in the early game and when I go to the plaza he is not there at any time. have I soft locked myself out of getting to the tailor

Apparently, you spend too much time on sex and do not develop Celica's skills at all.
Buy more magic items, improve them in Morden's laboratory and use them more actively in Celica's work.