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 ;)

@SpatzieLover You took all the good ones! :)

Where do you work?
Do you enjoy your job?
What do you miss about HS?
Are you married/kids?
Are you still driving that ‘71 Pinto?

You can also use current events, like

What do you think about the Berlin Wall which fell 20 years ago? Like many I watched the celebrations yesterday on tv. Did you?

ask her something you would ask fluther.

Questions relating to the “good old days” in high school are a good start, like @SpatzieLover and @ThePeanutGallery mentioned, but after a while you’ll probably want to get into less superficial discussions. Once you establish a closer relationship with your correspondent, you’ll find that these discussions can get pretty intense (and lengthy!) At that point, my problem is that the emails get too long and I have to figure out ways to cut them down.

Of course, when you’re feeling that your conversations begin to wind down, these simple questions always make for good “jumping boards” for new conversations. :)

Ask her how she is, what’s going on with her and her opinions on the big questions in life…

I would also include some information about you and where you are now in your life… so that you can bridge that gap between you and maybe become better friends. :-)

questions you think she would answer, :)
or maybe the usual what do you want to do when we finish college?
ok maybe thats not usual but just ask things that you maybe want to know about her
:) g,luck

^ agree. people love to answer questions they know the answer to.

You don’t have to interrogate her. Play some games. Write the beginning of a silly story and tell her to continue it for a bit and send it back. Or take an official letter from someone and artfully “censor” the letter with a sharpy to make it funny. Encourage her to do the same. Or any time you see something funny or crazy, clip it out or print it out and send it along. Getting a clip out of a funny B.C. comic with a quick note scribbled on the back can be just as good as getting a 4 page long “Dear Aunt Sally” letter.
Just some thoughts,
-Dan

Personally, I would only ask questions you genuinely want answers to. If you have no questions talk about things that interest you.