Deep Ass Starters.
Sometimes it's hard to get in depth with your muse and their backstory, because you can't figure out how to bring those things up with others. Here are a couple of starters intended to make things a little more personal!
"What's holding you back?"
"I'm not comfortable with this conversation."
"Will you /ever/ be comfortable with this conversation?"
"Let me in sometime!"
"It's not that easy, you know."
"Help me understand."
"It's hard to connect with someone when all they do is push you away."
"Why are you always so cold?"
"Why are you always so happy?"
"Are you really happy now?"
"Who hurt you this badly to make you this way?!"
"What, did your ex mess you up that badly?!"
"Why do you keep fighting it any time you feel?"
"It's a problem, I get it."
"This is all kinds of messed up."
"That's not exactly a good coping method."
"So what happened, with your parents, really?"
"What was your childhood like?"
"Everyone has at lest a little bit of mommy/daddy issues. It's nothing to be ashamed of."
"My parents aren't exactly perfect models, either."
"You were bullied? What for?"
"Was it hard? Coming out, I mean."
"You can't just run away all the time."
"You can't just hide all the time."
"Are you still thinking about them?"
"I'm not the enemy here. But this makes me wonder who the real one is for you."
"Is the reason you're so cold and defensive because you feel threatened?"
"How long has it been since you last spoke to them?"
"You never talk about it, why?"
"How come you're so different around them?"
"It's like you don't have a care or worry in the world."
"You seem so perfect. I don't get it."
"What was your ex like?"
"I don't think I was ever good enough for them."
"Are you not comfortable being intimate?"
"Why don't you feel comfortable being intimate?"
"Letting someone see you that vulnerable, it's a scary thing."
"Are you scared of being hurt?"
"Have you ever been taken advantage of?"
"Why are you afraid of saying I love you?"
"I never understood how someone could say those words so easily."
"You're hurting others the way you've been hurt in the past, don't you think that's ironic?"
"You use people to make yourself feel better."
"I'm scared of being used again..."
"Losing someone isn't easy, but you're making it harder than it needs to be."
"How long has it been since you lost them?"
"You're too attached."
"I'm not attached, I'm just comfortable with what I'm familiar to."
"Maybe the real reason you're so controlling is because, deep down you'd rather have them in your grasp than lose them."
"Why did you ever break up?" / "Why did we ever break up?"