We're just trying to get to know each other this Friday at downtown. What are some good conversation starters to avoid the awkwardness?
Most Helpful Girl
Read some crazy but recent news stories you can bring up like "oh did you hear about ___________ that happened last week right near here?".
Ask her what her favorite restaurants are around the area and the types of foods she likes most, maybe go on to favorite candy/desserts and maybe you two can go get some dessert?
Ask what genres of music she listens to and ask if what concerts/events she's been to.
Compliment her on something; how her hair looks, nice smile, nice laugh, etc.
Read some actually genuinely funny jokes online and memorize them to tell her randomly (if you can make her laugh it will lighten the moment).
If she has a job ask her about what she thinks of it, what she does exactly, what she aspires to do with her career. If she is in school ask about her program, if she likes it, finds it difficult, what her schedules like, etc.1