The post you've all been waiting for! Many thanks to all those who submitted ideas. If you have additional ideas, please either post them as comments on this post, or email me.
Please note: these topics are satisfaction guaranteed or your money back. Oh, wait, they are free? Oh, well I guess they aint guaranteed after all. Use em at your own risk!
This list is in no specific order, and some topics are best discussed on later dates.
1) What you do in the summer
2) Teachers/ Rabbeim/ Professors
3) School/ Yeshivah/ Seminary/ College
8) Current Events
13) Intriguing things
14) Pictures on the wall
20) Interesting things you have seen
23) Ambiance of room/ Hotel/ Venue
26) Why you chose the school you went to
27) Glasses/ Contacts
32) Yomim Noraim
36) Jewish Geography
37) Sibling's personality
38) Parent's personality
39) Which middos are you machshiv
40) What values do your parents emphasize in their house?
41) What values do you plan to emphasize in yours?
42) What do you believe is the purpose of life?
43) What are you looking for in a spouse?
44) Why do you want to get married?
46) Dating itself
48) Family minhagim
50) If all else fails, discuss BOSD!