5. “Let’s stop for a quick cup of coffee.” Keep the pressure low.
Rather than making an official weekend date plan, ask him out on a quick coffee break. If a café is nearby where you two have to go, it’s even better. Ask him to make a quick pit stop. If he’s inexperienced, he may feel intimidated at the thought of spending a whole day with you, but a 20-minute coffee break is much more do-able for him. Be creative with your tactics, summon up your courage, and ask him out!