The first thing I will say is that there’s only so much you can fake. In reality pretending to want to get to know someone will eventually show. You will forget certain facts about the person or you may ask the same questions over and over again. Therefore the #1 rule in building comfort and rapport with someone is: ACTUALLY GET TO KNOW THEM.
One of the quickest way to build comfort with someone is to find things that you have in common. Therefore try and ask questions that both stimulate conversation and help determine the personality type they are. For example:
“If you were dying on Sunday and you had one music festival to see before you go. Name 5 headliners that you’d have to see.”
“You’re at Coldstone and you have unlimited Mix-Ins. What would you add”
“Would you rather fight 100 duck sized horses or 1 horse sized duck”
“What could you eat everyday and never get sick of”
“Would you rather people think you’re super smart or super sexy”
“What is your biggest fear both physically and emotionally” (Save this for Higher Levels of conversation)
Remember that texting gives you one big advantage. The woman will have less of a shield than she would in person. She controls the conversation. At any point she can stop talking to you forever and not have to fear any physical risk of getting hurt. Use this to your advantage. Be funny and creative with your questions. When she asks you something, give her a couple of silly answers. Be perceptive with her answers. If she says she’d see 5 different styles of music, tell her she must be very eclectic with her tastes. If she says she fears being alone, tell her she must have people in her life who make her feel secure. By being perceptive of her answers, and using it to guess deeper aspects of her personality, she will build comfort with you.