Never had any problem with it.
For girls:
1. compliment him on his parking/driving (especially if he stands back to admire his parallel parking…. that’s your cue)
2. Let him start and direct the conversation, but don’t be afraid to speak up and say what you think (boys don’t generally get hints, and they don’t get offended easily)
3. Smile when you talk
4. On a first date, do not bring up anything controversial. Starting the second date, you can bring up more interesting topics. On the first date, let him decide where the convo will go.
5. Ask him about himself… his favorite summer, class, future plans, etc. Ask him if he could tell you a little bit about his yeshiva (they LOVE talking yeshiva politics!)