In my headcanon, there's times where Gary gets insecure and thinks that he doesn't deserve Serena.
For the most part, Gary doesn't get jealous when some guy flirts with Serena, but during these times where he's insecure... well..
Serena will sometimes get slightly annoyed about it because she has already told him a million times that she isn't gonna leave him, but for the most part, she appreciates it.
The reason Gary started getting insecure in the first place is because he believes that Professor Oak pays more attention to Ash nowadays and is more in Ash's life than his, and he will sometimes worry that Serena will do the same to him one day (although she repeatedly tells him she won't). Serena is a very important person to Gary, unlike his exes, so this is why he does this with her.
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~The Book Of Rivalcrushshipping~
RandomI really need a book dedicated to my OTP, so I'm making one. Lol I got way too lazy, so I made the cover the exact same one as my Rivalcrushshipping Story Cover. XD