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The first major time they had a good relationship was in Culture Shock, Squidward allowed Gary to be in the Krusty Krab Talent Show. Another time they had a good relationship was in Giant Squidward they share they same thing about Spongebob being annoying Squidward replied "Oh, tell me about it!". Another time was in That Sinking Feeling, , Squidward was searching SpongeBob in his house and when he spotted Gary on the roof, he said "hi" to him, though this was brief.
Though they get along sometimes there are rivals in I was a Teenage Gary Squidward almost killed Gary. In Can You Spare a Dime? Gary calls Squidward a free loader as the latter calls him other bad names. In The Great Snail Race, Gary forcefully races against Squidward's snail, Snellie. In Once Bitten and Little Yellow Book Gary bites Squidward. In Patty Caper Gary describes another suspect—Squidward, in stealing the Krabby patty secret formula. In The Thing, reveals that Gary attacked Squidward violently. When Squidward turned into the thing, Gary violently attacked Squidward again, Though Gary didn't know he was Squidward.