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How Not to Bore Your Date

November 26, 2020 | by Aleeza Ben Shalom

Mastering the art of conversation.

Starting conversations on the first few dates can be challenging. How you present yourself can make or break the potential for a relationship. How do you tell your life story without boring your date, and convey the salient insights your date needs to get you?

Here are some dos and don'ts on how to get the conversation rolling:


Before you go on your date, give yourself a pep talk. Remember: your story matters, you matter, and what you will share with your date matters. Don’t psych yourself out, psych yourself up! Show up on your date with a positive attitude. This is the best way to put your best self forward.


The beginning and end of your date are crucial and memorable points in your time together. Don’t complicate them with heavy conversation. The deepest part of your conversations should happen in the middle of your date. Your greeting should make your date feel good and connected to you. So be friendly and end warmly, leaving open a possibility for another date, if you so choose.


It is important to be intentional when choosing the life experiences that you will share on a date. Try not to share stories just for the sake of sharing. Choose aspects of your life to share that will truly show your date what has made you who you are today, what kind of person you are, and your ambitions for the future. Some great questions to ask yourself as well as your date include: What are my primary goals in life? What are my core values? Why did I choose this career? Am I satisfied with it? What really makes me happy? What are my secret dreams and ambitions? Why haven’t I fulfilled them yet? And remember, it's a give and take conversation so make sure to ask your date about their story as well.


For many singles this is one of the most difficult things to do on a date. As mentioned above, to share a story just for the sake of sharing isn’t reason enough. You are telling your story in order to show who you are, your values and beliefs, or to show something you two have in common. To truly connect you must be vulnerable and open up to your date. Try sharing something you don’t normally share with others. This does not mean you should disclose any extra personal information you are not comfortable with sharing, but getting to know a date requires a different sort of conversation than if you are just getting to know a friend. Your conversation does not have to be especially heavy, but make it meaningful. Remember, you and your date are not in competition to out-story the other person. If you have something meaningful to share that will help you connect, share it.


Location matters. If you're looking to form a deep connection with your date through conversation, you need to pick a place where you can focus and feel comfortable. Avoid loud or crowded areas like busy restaurants or parks with a lot of people (kind of easy to do these days). Choose somewhere you can be free from distractions to allow for a more intimate atmosphere. The less public a place is, the easier it will be to open up. Where you’re most comfortable, you’ll be most interesting. Maybe you're most comfortable while taking a walk so you aren’t forced to look someone in the eye. Maybe you prefer to sit face to face over a cup of coffee and look your date in the eye and receive that visual feedback that shows that they “get you.”

And if during the pandemic you go on a virtual date, make sure you set yourself up in a private space and good wifi connection!

Sometimes there will be an unavoidable awkward silence. This is okay. Better the occasional silent moments then fill the space with meaningless rambling. May you get comfortable with being uncomfortable and find someone wonderful to converse with.

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