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On the one hand, Paul supported both the observance and non-observance of special days as equally valid options in Romans 14:
No, they were two different audiences with different contexts. Paul wrote to the Romans, a mixed congregation of Jewish and Gentile Christians. If they wished, the Roman Jews could observe special days but didn't insist the Roman Gentiles do the same. On the other hand, the Galatians were Gentile converts. They were being pressured to adopt Jewish special observances. Paul told them there was no need. He advocated for mutual respect and tolerance in non-essential matters.
On the other hand, he was against observing special days in Galatians 4::5 One person considers one day more sacred than another; another considers every day alike. Each of them should be fully convinced in their own mind. 6 Whoever regards one day as special does so to the Lord.
Did Paul contradict himself?8 Formerly, when you did not know God, you were slaves to those who by nature are not gods. 9 But now that you know God—or rather are known by God—how is it that you are turning back to those weak and miserable forces? Do you wish to be enslaved by them all over again? 10 You are observing special days and months and seasons and years! 11 I fear for you, that somehow I have wasted my efforts on you.
No, they were two different audiences with different contexts. Paul wrote to the Romans, a mixed congregation of Jewish and Gentile Christians. If they wished, the Roman Jews could observe special days but didn't insist the Roman Gentiles do the same. On the other hand, the Galatians were Gentile converts. They were being pressured to adopt Jewish special observances. Paul told them there was no need. He advocated for mutual respect and tolerance in non-essential matters.