text: how do you flirt with a girl to make her entertain always? i have been flirting with a girl before. but that makes her boring. i really don't know what other way i can do. my social skills are very poor and my shyness doesn't help. i'm not sure if i understood your question correctly, but if you are looking to flirt like a pro my number one tip is always leave when the conversation is at its climax. never wait until the conversation dulls down, e.g. awkward silence, to say something like, "i should get going." if you leave when the conversation has peaked, it makes her think you're interesting and leaves her to look forward to your next encounter. thus, by the time you meet again hopefully you will have a great, entertaining story to tell her.