5 Messages That Encourage Him to Ask You Out on a Date

2. Tell him about a place you feel like going to: “I feel like going to an amusement park. What do you think?”

Telling him what you feel like doing can give him the sense that it’s his mission to take you out. A guy in his 20s said, “If she wants to go somewhere, I would love to take her.” Think of a reason that might hype him up, such as saying, “I haven’t done something exciting in a while.”