I'm not positive about the number, but it's the episode right after Neji, Naruto, Shikamaru, Chouji, and Kiba get back from chasing after Sasuke with Temari, Kankuro and Gaara. He's crying because he thinks Chouji and Neji are going to die and he doesn't want to feel responsible.
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Episode 220 but she says "At least this time you didn't get all choked up" but in the manga volume 27 page 13 she tells him "You need any help, just gave us a ding got it crybaby?"
Naruto Episode 135- The Promise That Could Not Be Kept Shikamaru finally cries in this episode. Around 9:20 or something like that.
Episode 129-135 are so saaaad!
Because Tsunade is afraid that she might lose Jiraiya too cos he's going to a dangerous mission alone that he might die ,that we all know that that's going to happen when he fight Pein. also cuz she loves Jiraiya <3 She's known him since she was a littl kid and she doesn't want to lose him, she loves him more like a brother than romantically though (although she does love him romantically somewhat but not as much as family-wise) :)
Season 5|Episode 15 Boys Do Cry
ahhh, my favorite! Inuyasha: The Final Act Episode 9!
Boys Do Cry
The song that played in Naruto episode 217 about halfway in the episode is Closer by Joe Inoue.