Jane Rizzoli: Have you ever experienced something traumatic?
Maura Isles: Have you ever been bullied for one of your quirks?
Barry Frost: Are you good with computers?
Vince Korsak: What’s your favorite animal?
Frankie Rizzoli: Have you ever felt like you were living in the shadow of someone else?
Angela Rizzoli: Can you cook? If so, what?
Sean Cavanaugh: Have you ever been the boss of something?
Susie Chang: Have you ever walked in somewhere and interrupted something/someone?
Charles Hoyt: Ever fool someone else?
Tommy Rizzoli: Ever done anything illegal?
Casey Jones: Ever felt unwanted?
Rondo: Ever get a ridiculous adorable nickname from someone?
Stanley: Ever been in the wrong place at the wrong time?
Paddy Doyle: Ever left someone’s life for good reasons but wanted to be there anyways?
Jo Friday: Ever changed the way you look just because?
Lydia Sparks: Ever gotten sympathy from strangers?
Hope Martin: Ever make a poor decision that caused someone else harm (physically/emotionally)?
Frank Rizzoli, Sr.: Ever walk out on something good?
Gabriel Dean: Ever felt like a third-wheel?
Giovanni Gilberti: Ever dated someone perfect and somehow messed it up?
Cailin Martin: Have you ever been ungrateful for something you’ve gotten?
Rafael Martinez: Have you ever made a mistake that cost you a friendship?
Dr. Pike: Have you ever had a seemingly brilliant idea that everyone else thought was stupid?
Constance Isles: Can you speak another language?
Joey Grant: Are you still close to someone from your childhood?
Riley Cooper: Do you have any tattoos?
Sister Winifred: Are you religious?
Dennis Rockmond: Are you artistic?
Garrett Fairfield: Favorite prized possession?
Ian Faulkner: Favorite place you’ve ever traveled to?
Delete this when reblogged: I made these up because we need some for our fandom! (Do we have any?!) Feel free to add to the list, though I think I’ve covered the majors. If you want to change the question for someone, let me know! (These are so random, but I tried to ask something that went with the character!)