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The Art of First Date Conversation


It’s time to meet. You met someone online, but now you want to take the next step. You have followed all the safety criteria:

  • Agreed to meet in a neutral, public place that does not demand a lengthy time commitment (e.g. a coffee shop rather than a French restaurant)
  • Told your family and friends where you are
  • Set a time limit of about an hour for the first meeting, to assess the potential for a second date

So you followed all the criteria. That’s all well and good, you say, but now you have a date set up for Thursday and you are starting to get the jitters. You may be thinking: “What will we talk about? What if I talk too much? What if I don’t talk enough? What if I’m boring? What should I ask?”

Don’t panic. Take a deep breath and do your preparation. You wouldn’t plan a meal without going shopping and you wouldn’t go on vacation without an itinerary, so why go to a first date without laying the groundwork? It will simply provide you with a plan of action, and make you feel more confident. And as we know, confidence is sexy.

How do you prepare? Focus on the skills of conversation and topics of interest. If you are already an easy conversationalist, it is still normal for you to feel nervous in this situation, so cut yourself some slack and go back to basics with me.

Smile. A brilliant way to start out. Although it may seem obvious, sometimes in our anxiety, we can come across as a little too intense at first if we don’t remind ourselves to… smile. A smile lets the other person know you are pleased to see him or her and the smile will be returned.

Eye contact. Maintaining good eye contact in our culture is important. Eye contact does not mean you never glance away. Notice next time you are in casual conversation with a friend or colleague. There is a normal amount of looking away mixed in with steady, focused eye contact. When you look someone in the eye, it shows that you are fully engaged in the conversation and listening to what the other person is saying.

Connect. A very important way to connect personally is by using someone’s name. Doing so validates him or her and creates a deeper bond. You convey that this person is not just “one of many” or “one in a crowd” but a person you see and hear as an individual and about whom you hope to know more.

Body language. As I’ve mentioned in previous blogs, the non-verbal language of the body is “heard” loud and clear. Open body language will put the other person at ease and will say, “I’m interested.” This posture includes standing or sitting tall, with head high, arms relaxed, leaning slightly forward and facing your date directly. You want to appear comfortable, not bored. You want to come across as confident, not arrogant. You want to be accessible, not vulnerable.

Now for conversation. The more you practice, the more at ease and confident you’ll be.
To decide what questions to ask or topics to discuss consider what your requirements, needs and wants are in a relationship. Also, know what you want to share. Keep in mind that the meeting is to determine if this is someone you would like to spend more time with.

Breaking the ice. Keep conversation light and upbeat. Chances are you both are a little nervous, so a light, even humorous, conversation is the best way to start out. An easy way to build a connection is to talk about a topic that you can both relate to. It could be a current event or swapping funny online dating experiences. It is not the time to talk about your ex, problems at work, your health or anything else “heavy.” You should have fun talking with your date even if you pre-plan some topics.

Exploration. Getting to know your date. By now you’ve had at least one phone conversation. Maybe you remember movies or hobbies he or she mentioned during the call? Or favorite music, or being a pet owner? If so, you can start a conversation with questions:

  • “What did you like about that movie? Who was in it?”
  • “How did you become interested in your hobby?”
  • “What type of music do you love most?”
  • “Tell me about your pet.”

Follow up questions show engagement, and have the added benefit of accelerating your discovery of common ground you might share.

If you are looking for a committed long term relationship, ask questions that gently probe to assess if that interest is shared.

  • “What are you most passionate about in life?”
  • “What are your goals for the next ten years?”
  • “Do you believe in happily ever after?”
  • “What brings you the most pleasure?”

Avoid overly-intense queries that might seem scary on a first date, such as, “When can I see you next?” or “Would you like to meet my children?” If you sense the person is uncomfortable at any time, back off. Also, mixing in lighthearted conversation with questions will eliminate the feeling of an interview. Listen sincerely and attentively. Give him or her ample room to talk. Doing so shows that you are interested in the conversation and want to hear more.

Personal anecdotes. It is just as important to share about yourself as to find out about your date. Telling a funny story from work that reveals something about the way you interact with people can be enlightening. Talking about a favorite vacation can be insightful for both parties as your date can learn about you and may share a love of traveling as well. As you share stories about yourself, avoid mention of an ex (even if a trip was or a hobby or interest was shared with one), and stick to upbeat, lighthearted anecdotes, avoiding the overly dramatic or painful

Sharing yourself also gives your date an opportunity to ask you questions. Do not deflect those questions, even if you are shy to talk about yourself. The goal here is to get to know one another, so be open and honest. Finding a balance between how much to talk and how much to listen is challenging. Keeping tuned in to body language is part of knowing if you are hitting it right. If your date pulls back, glances away from you more than is normal or starts saying, “Uh huh” a lot, shift the focus.

Do you want another date? If you had a good time with your date, say so. It will be appreciated. Arrange to meet again, or to talk or email to set up a date. If you didn’t click, you can still be kind. Warmly wish him or her well, and part on good terms.

The best first date conversations are fueled by the comfort of both participants, so don’t get obsessed with asking a list of specific questions that turn a conversation into an interview. Allow the conversation to have a life of its own. If you don’t get to most of your questions, or any, it just means the conversation spontaneously worked, and that is a good thing! Going in with a plan is an excellent strategy, regardless.

Remember to relax, have fun and enjoy your dating journey.

Filed Under: Dating & Relationship Advice, First Dates

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