First Date Doldrums How To Liven Up The Conversation

Women's Dating

First Date Doldrums: How to Liven Up the Conversation

C. Price

Written by: C. Price

C. Price

C. Price is part of's content team. She writes advice articles, how-to guides, and studies — all relating to dating, relationships, love, sex, and more.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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So you’re on your umpteenth first date in the last month and instead of responding to your date’s questions in an exciting and charming way, you catch yourself repeating your go-to answers like a bored teenager practicing a Shakespearean monologue for English class.

It’s true first dates can become repetitive, especially if you’ve been single and looking for a while. But there are ways to break up the monotony that can be single life.

Come prepared.

Spend a couple of days before your date coming up with your most original questions and responses. Ask your family, friends and co-workers if they can think of a creative question to ask and test those questions out on them. Maybe they have an interesting story from one of their first dates you can take inspiration from. Sometimes asking others about there experiences can give you a different perspective.


“On first dates there’s always the

chance of making a connection.”

Go bilingual.  

If you or your date speaks a different language, suggest alternating back and forth between English and another language. If you don’t speak similar languages, let him teach you a few words. Or you could teach him a thing or two. You will come across as cultured, sexy and charming, while also challenging your date to see if he’s really listening. Of course, don’t do this during the entire date because that might slow the conversation down.

Rearrange typical topics.

Instead of asking him where he sees himself in five years, ask him what his life was like five years ago and how has he accomplished his goals or changed his objectives. You still learn about his aspirations and get a better understanding of how he became who he is today.

Rather than talk about your favorite movies or books, discuss which of those favorites would best describe your life, or ask him which one is the opposite of his life and which he wished was similar to his life. This will give you insight into who he is while also discovering his likes and dislikes in a new way.

On first dates, there’s always the chance of making a connection, or at least having a funny story to tell your friends later, but finding someone to go beyond the first date can be a challenge. If you find yourself in a first date rut, give these tips and tricks a try.

You may not find the love of your life, but you might have a good time.

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