5 Techniques for Meaningful Conversation in Dating

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How to go from casual conversation to a deep, meaningful one.

A client of mine had been dating someone for two months yet still didn’t feel a strong connection and was about to break it off. There was no red flag or reason to break up, but there wasn’t anything holding the relationship together either.

I advised my client not to break it off just yet. We worked on bringing the relationship to the next level by deepening their conversation.

Meaningful conversation is one of the best ways to bring two people closer together and forge a lasting relationship.

1. Explore someone else's beliefs. Try to understand their thinking and reasoning. Don't try to agree, disagree or get them to see your point of view. Rather, be curious about what they believe and think. Try to get in their head and really understand what they are saying and why they believe what they do. The more you understand someone, the more connected you will feel to them – and them to you.

2. Talk about personal interests and passions. Hobbies are usually personal interests that stem from something deeper within you. Think about something you’ve been working on in the last week or month. Did you learn a new song on your guitar? Are you working on a painting for a friend? Are you working out and training for a half marathon? If you don’t have a hobby, maybe it's time to find one you genuinely enjoy.

3. Ask a question to get a story. Don't ask a question to get an answer; ask questions that prompt your date to tell you a story. Instead of asking, "Do you like your work?" try, "What is the most interesting part of your job?" Through the storytelling you'll learn more about the person. You'll also have the opportunity to follow up with comments or questions about their experience that can lead you to deeper understandings and insights.

4. Get personal…but not too personal. When you share, others are likely to follow your lead and start to share with you too. Don't share about the time you threw up all over your date...but do tell a story and share a memory of your favorite birthday party. Who and what made it so special? (My basic tip is to try to speak about positive personal experiences as opposed to negative ones, as sharing negative experiences might leave someone with a negative impression of you.)

5. Talk topics: similarities and differences. Sometimes discovering how you are similar can help you to see where you connect. But differences can make the relationship interesting or challenging. One easy way to figure out where you align and where you differ is to ask random questions like: Would you prefer to be comfortably dressed or painfully stylish? Was your first impression of me on target? Do you remember your dreams or have any recurring dreams? Are there any movies you've watched multiple times? If you could do one thing for someone in need who would you help and why? If you have siblings, what is your relationship with them now and what do you hope that relationship will look like in 10 years? Who believes in you the most? In what way are they supportive? Discussing your similarities and differences can not only help you to understand the other, but to appreciate them and what makes them unique.

It took time for both sides to open up, become comfortable and really share from within. After two more months of slow progress, my client and her date began to feel more comfortable with each other and open up and share. My client started to see a shift in the relationship and thanked me for helping to prevent a breakup before the relationship had had a chance to blossom.

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