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Well towards the end of the second season of Digimon,Tai goes to Sora,who was at Matts concert on Christmas Eve about to give her flowers,but Tai found out that the reason she was at Matts concert was that she was gonna give Matt some homemade cookies, Tai felt embarashed so he didnt tell her, later Sora did end up marrying Matt

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Q: Does tai ever tell Sora how he feels in Digimon?
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