Everyone is a little nervous on their first date with someone. Frequent lulls in the conversation could make it even more awkward. The trick is to simply ask open-ended questions that could lead deeper into a conversation.
Start the date with some good general questions and then as time goes on, you can make the questions more interesting.
Some good general conversation starters are questions like…
How was your day today?
How do you like your job?
Where are you from?
What do you normally like to do on your days off?
What kind of music do you like?
As time goes on and you start to feel a little more comfortable you can start asking some unusual questions that will really get the person thinking and could give you a lot of insight into their personalities. Such as:
If you can live in any home in a television series what would it be?
What is your favorite website?
What is the most unusual costume you ever wore to a Halloween party?
Where were you on 9/11/2001?
What is your three all time favorite television sitcoms? (If they are ones that you know well, ask; Which were your favorite episodes? This is a good one because it can also lead to a lot of laughter as you remember your favorite one liners from popular comedy shows.)
What is the most memorable class you have ever taken or the most unusual teacher you have ever had?
If you could have any kind of superpower what would it be?
What infomercial drives you crazy every time it comes on?
Who is your all time favorite actor?
If you found $10,000 in a bag on the street with no identification, what would you spend it on?
What is your all time favorite “spoil yourself” meal or dessert?
Is the glass half empty or half full?
Peanut butter and what?
What is the worst concert you have ever been to?
Ever hit a jackpot on a slot machine?
What are your pet peeves?
What is the best meal you have ever eaten?
What is the scariest moment you have ever had?
What is the best time you have ever had with your family?
What is the most shocking end to a movie you have ever seen?
If you could spend a day with any 5 people, living or dead, who would they be?
If you could have free, unlimited service for a year from a professional cook, chauffeur, personal secretary, housekeeper or masseuse, which would you choose?
What was the best present you ever got as a kid?
If your life was a television show what would the main storyline of the show be about?
What would you call the show?
What is your favorite board game?
How early do you start holiday shopping? Months in advance or last minute?
When you were a kid, what did you dream of growing up to be?
What is your first memory?
What was your favorite toy as a child?
If you could be any kind of animal, what would it be and why?
Have you ever met any celebrities in person?
Even just a few of these questions will keep the conversation going all night long and provide a little laughter as well as a lot of insight into the person.
Just remember to pay attention to what the other person is saying so you will be able to respond intelligently.
Before you know it, the evening will have flown by with both of you having an enjoyable time.