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Best Conversation Tips For A First Date

First dates can be challenging, especially when it comes down to knowing what to talk about. Our WikiWoo dating expert, Hunt Ethridge shares his best conversation tips for first dates so you can score that second date!

WRITTEN BY Hunt Ethridge | Guest Writer | Apr 09 2018

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I know that a lot of people dread first dates. However, I used to love them! For me, there was a whole new person that I got to learn about. I can ask her ANY question in the world, as I don’t know anything about them. At the same time, I get to talk about the things that make me happy as she hasn’t heard any of my stories or stale jokes! My personal mantra in life is, “Everyone has something to teach me. Whether it’s 30 years or 30 seconds, my job is to learn from them.” So every time I met someone new, I felt that I gained more as a person. Now I know what growing up in Iowa is like. Or I have a fuller understanding of what a neonatal nurse does. So after every first date, I felt pretty good. Some were better than others, yes. But generally, I enjoyed them. Part of that is that I feel comfortable in my skin, so it allows me to feel relaxed and confident. The other aspect is that I knew what I wanted to talk about, knew how to have conversations and could help out others by bringing their emotions out and getting them to relax and have fun. So if you have a bit of a script, game plan or some funny stories, it’s going to help you chill more and have more fun.

Ask Positive Emotional Questions

All this means, is that you want to make your date feel good. Some people do it the cheap/easy way and lay on compliments. Yeah, compliments are good, but they are like salt. Not enough and it’s unexciting and too much puts a bad taste in your mouth. However, the better way to make someone feel good is to ask them about happy things in their life. Have you had happy and wondrous things happy to you in your life? Of course you have! Does anybody ever ask you about them? Most likely not. Same with the other person sitting across from you. They have danced, travelled, seen friends get married, cuddled a pet, been recognized, gotten a promotion, etc. Instead of pulling out the same boring questions (Where are you from? What do you do? Where do you live?), try ones like, “What was the best meal you’ve ever eaten?”, “What teacher inspired the most passion in you?”, “What’s one of your favorite memories from childhood?” or “What was the most interesting city you’ve ever been to?”

Tell the Right Kind of Story

“OMG, that reminds me of the time I….” Trading stories back and forth is a great way to bond and learn about each other. But you want to make sure that you’re telling the right kinds of stories. While stories are a way to impart information and entertain your date, they are also windows into who you are as a person. While you may think that the story of the time you crashed Rihanna’s party and ended up throwing up in the limo is hilarious, it might not be the right story for a first date. Instead, think about the character or personality traits that you have that you would like them to know about. Are you a good dancer? A great cook? Are you super spontaneous or steadfastly loyal? Quick tip: never list, always describe. Instead of listing (“I like to ski, I like Cuban food, I read fantasy novels”), tell a story where your cooking/dancing/loyalty takes center stage. It’s easy enough to say you’re spontaneous. Instead, tell me a story about getting a last minute flight to Nashville to see your favorite artist’s last show. You should have a story for each trait that you want your date to know about.

Conversation is Tennis

Meaning, there needs to be a healthy back and forth rapport in order to build or foster chemistry. Now, I love to talk. Like, a lot. So one of the things that I do myself in order to make sure I don’t go off the rails on a 20 minute story is limit my comments to 5 sentences or less before I stop and send it back in their direction. Depending on what study you read, it’s said that women use 3 times the amount of words everyday than men do. I coach my male clients to talk and open up a little more and my women clients to be careful of monopolizing the conversation or going into too much detail. If they ask you a question, give a quick couple of sentences overview about it. If they want more details, they’ll ask you about it. To use another tennis analogy, you want to avoid whipping the ball back at top speed. Instead, give it a nice lob. Meaning when you ask them a question, make it an easy and pleasurable answer. “Yeah, I like beef too, but I can’t eat veal after watching a horrible documentary on it. How can you?” “….uh…..” Instead, “Yeah, I like beef too but not a fan of veal. Was there anything you used to hate to eat as a kid?” “Oh man, I hated mushrooms! They tasted like dirt!”

Many of my clients feel that by preparing ahead of time, it ruins the spontaneity. Nay, I say! Instead, it sets the stage to foster chemistry and keep things moving. If you are comfortable with where the conversation can go, it allows you to relax and focus on your date. Good luck and talk on!

Men's dating expert, online dating expert, wiki woo dating coach

Hunt Ethridge

Women's Dating Expert

Hunt Ethridge is an award-winning dating and relationship expert with over a decade of experience helping people become the best, most dateable versions of themselves. While the focus of his coaching is on making someone empirically more dateable, the lessons learned translate very easily into personal and professional lives. The emphasis is on confidence building, leadership, image & style, conversation skills, reconnecting with fun and more. He has founded 3 dating companies including the International Dating Coach Association which serves to educate and certify dating coaches and has members all across the globe. He has been featured collectively and individually on CNN, ABC, NBC, FOX, Vanity Fair, The Wall Street Journal, The New York Times, The New York Post, Maxim, the Huffington Post, Telemundo, Yahoo! Shine and more. He is considered one of the top in his field and is consistently called upon for insight, collaboration, and speaking engagements. As a prolific writer, he has over 100 dating advice articles all over the Web. He was recently voted the #1 Male Dating Expert in the country at the 2016 US Dating Awards. To read his advice articles, go to