First dates are often stressful for both people. Rather than going to a movie or concert, find a quiet place and spend time getting to know the other person. Icebreakers and conversation starting questions can reveal information that will help make a decision about future dates. Just be prepared to answer the same questions when they come back.
The Date’s Former and Future Relationships
To get right to the heart of the person’s relationship history and intentions for the future, be bold and ask.
- “Have you ever been in a long-term relationship before? If so, what caused the breakup?”
- “Are you looking for a long-term romance or someone to just hang out with?”
- “What are you looking for in a partner?”
- “Have you ever had a bad first date? If so, what happened?”
- “What is the biggest mistake a person can make on the first date?”
- “Have you ever had a first date when you knew there was something special? What made it that way?”
- “What is your idea of a romantic date?”
Special Interests, Sports and Hobbies
It’s a good idea to know if both people enjoy the same hobbies, sports and other interests. The first date is the ideal time to ask questions.
- “What types of books or movies do you like? Is there one standout book or movie you’d like to see more than once?”
- “What sports do you enjoy to participate in or watch?”
- “If you had a whole month to do anything you wanted to do, and money was no object, what would you do, where would you do it, and who would you do it with?”
- “What kinds of creative pursuits do you enjoy?”
- “Who are you favorite recording artists, and which of their songs do you like?”
- “Can you play a musical instrument? If so, what?”
School and Career of the Date
Education and career take up so many hours of a person’s day, knowing how the other person feels about these topics can affect the relationship.
- “How much education have you had? Would you ever like to go back to school? If so, what would you want to study?”
- “Are you in a career you like? Is it something you’ve always wanted to do? If not, where do you see yourself in five years? Ten years?”
- “If you could have any job you wanted, and education, money or experience was no object, what would you want to do?”
The person’s family history can provide valuable insight about what to expect in a future relationship.
- “Where were you born, and where were you raised?”
- “How many siblings do you have? Are you close to any of them?”
- “How often do you talk to other members of your family?”
- “What do you like to do when you get together with your family?”
- “Did you live with both parents, or do you come from a single parent family?”
- “Do both of your parents work? What do they do for a living?”
Challenging Questions to Ask on a First Date
Try to think of something different to ask – something unique that might make the other person smile, laugh or ponder.
- “Have you ever had a life changing event? If so, what?”
- “If I were to go to your house or apartment, what would I find in your refrigerator right now?”
- “Is there anything weird or unique about you that you’ve never told anyone else?”
- “Who is your least favorite singer? Why?”
- “If you could be any animal, what would you be?”
- “How do you feel about plastic surgery?”
- “What is your most valuable or treasured possession? What would you do to keep from losing it?”
- “Which is scariest to you: parachuting, giving a speech to a thousand people or kissing someone for the first time?”
- “What embarrasses you more than anything else? Have you ever been embarrassed in front of a large crowd of people?”
After the questions are asked, relax and enjoy the other person’s answers. Be ready for the tables to turn with questions about former relationships, interests, hobbies, sports, jobs, school, careers and some more challenging questions.