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

4. Act shy, but show interest in his stories: “Sounds like a cool place, but I don’t think I could go alone.”

He’ll want to show you around if you feel too nervous to do something by yourself. A guy in his 20s confirmed with us, “I would totally go with her!” Depending on what he tells you, you can change up your response, such as, “I would need a guide to show me around,” or, “I would be bored if I went alone.”