1 Work by Istoledabread
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Summary
Sonic has been acting kinda of odd? And Tails is worried and tired of his crap. Because what has Sonic been acting weird about? Shadow. And when 10 year old Tails doesn't know how to help these idiots, he goes to Eggman for help! And in the end, they are going to try recruiting Rogue to their matchmaking group (with Sage and Metal being honor members)
Or:
Sonic has a crush on Shadow and doesn't realize it, but Tails does. So he gets help from Eggman and Rogue to try to play matchmaker. (with Metal and Sage joining occasionally!!)