Line # 1: "Let me know if you need to vent."
Skip asking him what’s stressing him out. It’ll put him on the defensive. Instead, give him the option to open up without actually accusing him of being upset.
Line # 2: “I bet you killed that presentation today.”
Asking an open-ended question about his day will get you a “Fine” or “Okay.” Annoying. Compliment him and he’ll be more apt to dish the details.
Line # 3: “I have to tell you this story.”
There’s a scientific reason guys open up after you’ve shared something yourself—it’s called the norm of reciprocity. It triggers him to disclose more info than he normally would.