The first half-hour of the first date(s) is all about loosening up, breaking any tension and just … getting through it. Keep things lighthearted, natural and quite general.  Ask light questions with the intent to find something in common. When you are starting a conversation, not all topics will catch on right away. When something seems to catch both of your attention, hover on that topic and dive deeper.

First dates are not all about chit-chatting about random topics. The goal of the first dates is to get a sense of who the other person is. You both should be sharing bits about yourself in areas that are not that private.

​

Ask questions. 

People generally like talking about themselves and their experiences, so ask questions.

Every question you ask has the potential to narrow or expand the dialogue.  ​Start with a small question, then follow up with a bigger question to build the conversation.

• “Where are you from?” –> “How is that different from this city?”
• “What do you do?” –> “What brought you to that type of work?”

Ask questions that won’t put them on the spot, but will allow them to reveal more or less about themselves, depending on their comfort level. ​Use questions that begin with phrases like:

• “Tell me about…”
• “What was the best part of…?”
• “How did you feel about…?”
• “What brought you to…?”
• “What’s surprised you most…?”
• “How is that similar/different to…?”
• “Why…?”

Ask Open-ended ‘Why’ and ‘How’ Questions. An Ask open-ended questions  that cannot be answered with a simple ‘yes’ or ‘no’ or one-word answer. When you ask a “Why” question, you explore a person’s underlying motivation. 

Every conversation is an opportunity to learn something new.

People have different experiences, perspectives, insights and ideas. Ask questions to learn from the other person.  Be curious to learn something from the time you spend together. 

​Ask for recommendations or insight.  People love sharing their experiences and wisdom. “You know a lot about that topic, what’s a good book or blog to follow?“

When you discover a topic that the other is passionate about, ask, listen, ask.   

• “Tell me more.”
• “What is it like?”
• “How did you get into that? “

Be wary about bringing up your favorite topic.

​You’ll end up talking too much and not listening enough.  You may end up getting too passionate and try to convince them onto your side.

Avoid hijacking the conversation.

​’Hijacking the conversation’ means bringing the conversation back to yourself before the other person has finished their thought or story. 

Don’t do it.

• “Oh that reminds me of a time…”
• “You just went to Israel, I did too.  Let me tell you all about it…”

Of course, you can include your own relevant experiences and thoughts into the conversation, once the other person has finished.

Make it easier for the other person to expand the conversation. ​

When answering a question, reply with multi-facted response.  ”Last summer, I traveled to Morocco. We toured the ancient cities and hiked in Atlas Mountains. The kosher food there was so interesting.  What I liked most was meeting the Jewish community.” All those details give the other person lots to ask about or build on to continue the conversation.

Build on what they said.  For example, they say “Beautiful day.” Don’t reply with a simple, “Yes, it is a beautiful day today.“ Rather, add something that they can build on. “On days like this, we used to go to the park for a picnic.” Now you have given the other person something with which to continue the conversation.

When in doubt about what to talk about, bring up …

• the setting where you find yourself
• family (unless you know it is an uncomfortable topic)
• the activity you are doing currently
• recent travels
• a book you are currently reading

Create a master list of topics, stories and questions that you feel comfortable talking about.

Words to transition into another topic.

• “That reminds me of a question I want to ask… “
• “Not to change the subject, but I just [saw, heard…] “
• “By the way… “
• “I was really interested in what we were talking about earlier – can you tell me more? “

Try to make everyone you talk with feel a little better about themselves after having met and talked to you.

​You can ask for their insight or recommendation.  And then thank them after.

Acknowledge or compliment them   – their commitment, their sense of adventure, their curiosity. 

• “You seem so committed to that.”
• “That takes guts. Wow.”
• “It’s amazing how far you got in that. “

As applicable, tell them how you will incorporate their perspective or ideas into your life.  “Love that word you used. I’m going try using that.“

Body language shows your level of interest.

​Everyone’s body language provides hints to others during the course of a conversation, even if they don’t realize that they are doing it. Body language plays a big part in how others relate to us.

• Adopt an engaging posture. Leaning forward usually shows that you are interested. 
• Crossed arms make you appear cold, closed-off, or aggravated. 
• Slouching or moving backward can indicate a lack of interest. 
• Nodding, and genuine smiling shows interest.
• Make eye contact. Looking away can indicate discomfort with what you are saying or hearing. Of course, avoid eye-rolling, etc. 

Put your phone away.

Nothing says “I’m not totally with you” like looking at your phone.  You might actually show the other that you are putting your phone on silent as you put it away so that you can give your full attention to the date.

If you are expecting a very very important call, then state that up front  (“My boss will be calling to let me know if I am on call for the early morning shift.”)  But don’t be checking your phone throughout to see if the call or text came through.