4. “I’m free this weekend.” Make it easier for him to ask you out.
“The bar is set too high to ask her out. A small cue would be extremely helpful!” says a smiling young man in his early 20s. Even though he wants to ask you out on a date, he just can’t think of anything clever to say to you. In this case, if you crack the door open for him, it’ll be so much easier for him to gather the courage to ask you out.