A Matchmaker’s Guide To Having An Amazing Conversation During Your First Date 

As a matchmaking professional, I cannot begin to tell you how many fabulous first-date conversations led to long-lasting relationships. 

A Matchmaker’s Tips For Having Amazing Conversations During Your First Date 
Photo generated by AI

‘Love Notes by Chi’ is BrownStyle Magazine‘s column—curated by professional matchmaker Chi Love— that brings you insightful tips, and trendy discussions and answers your biggest questions about love, dating, and relationships.


Although first dates can be nerve-wracking, they are essentially the first step towards a potentially long-lasting relationship. As a matchmaking professional, I cannot begin to tell you how many fabulous first-date conversations led to long-lasting relationships. 

In hopes of helping ease any first-date jitters, I’ve decided to share my go-to tips to help you navigate conversations with confidence and grace. Good luck! 

Start With The Basics, But Make Them Engaging

Asking about someone’s job or where they’re from might seem mundane, but these questions are foundational. The key is to take these basics and add a twist. Instead of simply asking, “What do you do?”, try, “What do you love most about your job?” or “What inspired you to pursue your career?” 

These questions not only show genuine interest, but also allow your date to share their passions and motivations.

Share Stories, Not Resumes

First dates are about connection, not just information exchange. Share anecdotes that reflect your personality and experiences rather than listing achievements. For example, if you’re discussing travel, recount a funny or meaningful travel experience instead of just stating the places you’ve visited. Stories are memorable and help create a vivid picture of who you are.

A couple having a rooftop date
Photo generated by AI

Ask Open-Ended Questions

If you want to start a conversation, it’s important to ask questions that require more than a yes or no answer. Instead of asking, “Do you like music?”, try, “What kind of music do you love and why?”

Open-ended questions pave the way for deeper conversations and give your date the opportunity to share more about themselves.

Listen Actively

Active listening is crucial. Show that you’re engaged by nodding, making eye contact, and responding thoughtfully to what your date says. Reflect back on what you’ve heard with comments like, “That sounds fascinating,” or “I’d love to hear more about that.” This not only shows respect but also encourages your date to open up further.

Find Common Ground

Discovering shared interests can quickly build rapport. Whether it’s a mutual love for a particular hobby, similar travel experiences, or shared values, common ground creates a sense of connection. Use what you know about your date beforehand (thanks to your matchmaker!) to steer the conversation towards topics you both might enjoy.

Stay Positive

Keep the conversation upbeat and positive. Avoid controversial topics like politics or religion on a first date, as these can lead to unnecessary tension. Focus on light-hearted and enjoyable subjects that leave both of you feeling good. 

Be Genuine And Authentic

Authenticity is attractive. Be yourself, and don’t try to mold yourself into what you think your date wants. Share your true thoughts and feelings, and don’t be afraid to show vulnerability. Genuine conversations build trust and lay the foundation for deeper connections.

Use Humor Wisely

A good laugh can break the ice and ease any tension. Share funny anecdotes or light-hearted jokes but be mindful of your date’s sense of humor. Avoid sarcasm or humor that could be easily misunderstood. The goal is to make each other comfortable, not to impress with wit.

Observe Body Language

Communication isn’t just verbal. Pay attention to your date’s body language. Are they leaning in, maintaining eye contact, and smiling? These are signs they’re interested and engaged. Crossed arms, lack of eye contact, or checking their phone might indicate discomfort or disinterest. Adjust your approach based on these cues.

End On A High Note

As the date wraps up, express gratitude and genuine interest in seeing them again if you feel the connection. A simple, “I had a great time tonight and would love to do this again,” can go a long way. And even if you don’t see a future together, end the date kindly and respectfully.

Editor’s Note: This story has been edited and condensed for clarity. 
BrownStyle Magazine | Tabitha Brown | Special Fragrance Issue

By BrownStyle Magazine in Special Editions

72 pages, published 1/17/2025

Vanilla is like a warm embrace…In BrownStyle Magazine’s inaugural special edition magazine, explore everything vanilla—from an extensive fragrance guide to a personal essay about the nostalgia that comes with the timeless scent. We even chatted with everyone’s favorite “Auntie” Tabitha Brown about her Donna’s Recipe Whipped Vanilla collection and how she uses self-care to live a soulful soft life!

Chi Love is the CEO and founder of N.Y.A. Love and Dating Services. Affectionately known as the The Love Genie, the Professional Matchmaker and Dating Specialist enjoys working with singles from all over the US to find their true love.