Naruto father scenario

who he trusts you with

Naruto:
Kakashi because he saved Narutos ass multiple times he thought kakashi could protect you Incase you got into trouble

Sasuke:
Sai because sai knew how to help you with your mental health issues because he's been through them himself

Shikamaru:
Kurenai because she can help you when you on your cycle and she the best

Sai:
Shikamaru because ino trust him and sai trusts ino with all his heart so that means sai trusts shikamaru

Kakashi:
Anyone on team 7 because they've all been like second homes to you they're doors are always open for you when you need them

Itachi:
Konan obviously because most the people in the base don't know how to take care of themselves let alone a child

Neji:
Hinata and hanabi because he only trusted you with family and you've been scared of hiashi ever since he put the curse seal on you so they were the only family members you were close to besides ko and a few other but that hardly ever

Gaara:
Naruto because if not for Naruto Gaara would most certainly be in jail or dead by now and Naruto was Gaara's first friend so it's safe to say Naruto is the most trustworthy in Gaara's eye

Jiraiya:
Tsunade because you act ridiculous similar to her and she is like jiraiyas best female friend

Orochimaru:
Log because he's your favorite brother (sorry mitsuki) and your his favorite sibling (again sorry mitsuki) and orochimaru trust the brotherly bond you two have (and you also love mitsuki to death but you love log a little more)

Hashirama:
Madara ok I'm gonna be blunt their in a relationship that's way he trusts him with you

Tsunade:
No one (sorry jiraiya)

Rock lee:
Gai Sensei or as you call him Grandpa Gai and I think this one is obvious

Hiashi:
Any family members you trust because you never know what someone's intentions are

Inoichi:
Shikaku because they're married

Iruka:
Kakashi because Iruka he thinks that kakashi knows what he's doing (bad choice)

Shikaku:
Inoichi again they're married

Shino:
Kiba because he's uncle kiba and you love his dog