What did you major in college? What’s the weather like where you live? Do you visit “home” much? Who else do you stay in touch with from HS? What’s your best/worst memory from HS? Where was your favorite travel destination? What’s your favorite “go to” meal? When all else fails @evegrimm, get her to talk about herself, her hobbies, her interests, if she’ll go to a reunion, how her family is, if they still own the house she grew up in—etc. I’m curious by nature, so I ask questions to get the ball rolling. Then, I add details about what I’m currently doing, or not doing. You’re great at conversation from what I can tell about you here in Fluther. You shouldn’t have too much trouble once you get comfy emailing her. If she seems lonely you could always get her to join Fluther ;)