Breaking the Ice: Questions to Ask on a First Date


How you start your conversation on your first date can make or break your date. For example, you start talking to your non-alcoholic date by sparking a conversation about how you’re a heavy drinker and spend this morning recovering from a hangover. Such a start to the conversation will lead to an instant turnoff and most definitely not land you a second date with the person.

For this reason, I have taken the liberty of sharing with you the secret sauce for a great conversation that will help you grab the attention of the person you are talking to and get them to ask you out on a second date. To do this, I’ve collected tips from the best experts to help make your date perfect.

How to Break the Ice on your First Date

“First dates should be all about having a good time. Try to keep things light and enjoyable, and don’t take yourself too seriously. “ – writes Steve Carleton

When starting a conversation, try going off on a lighter note and then build up the conversation as the date progresses and you both start to get comfortable with each other. 

“Prepare a list of questions. Prepare a few questions before your date, so you won’t find it challenging to start a conversation with a new person once you’re seated across from them.” – recommends Marley Howard

For example, ask them about their drive to the venue or the weather rather than diving straight into their life history, siblings, and likes and dislikes.

As the conversation progresses into the initial ice-breaking phase, start with generic questions like if they like the environment/ambiance, ask them about the menu, and progress the conversation to their favorite food.

The key here is not to come across as too eager or pushy. This will send the wrong

message and make your date feel uncomfortable. Take things at their natural

pace and let them initiate contact.

“Don’t come across as too eager or too pushy. This will send the wrong

message and make your date feel uncomfortable. Take things at their natural

pace and let them initiate contact.” – says Nick Bach

Ice Breakers for a Fun Conversation

So you’ve set the foundation of your conversation by going about the conversations in a flow with some light-hearted Ice-breakers. Now comes the exciting part: asking your date open-ended questions to let you two know more about each other.

Joni Ogle emphasizes the importance of asking open-ended questions about your date. “Make sure to ask questions. This is a great way to get to know each other. Ask open-ended questions and focus on learning about the other person rather than trying to make an impression yourself. Try something like, “What do you enjoy doing in your free time?” or “What made you choose your career path?” 

Some Ice-breakers that can lead you to a fun and engaging conversation are asking them about their dream travel destinations, role models, favorite books or series, hobbies, etc.

Questions for Deeper Connections on First Dates

Talking to a date that shares no emotional connection with you can feel like talking to a wall. To elicit that deep chemistry with your date, you must be open with them. Share your values, dreams, and aspirations with them. 

The psychology behind this is simple. When you talk to someone by sharing things that are close to you and hold great importance for you, you are letting them know that you trust them with this information, and if your date ends up having similar interests as yours, then you both might feel that deep chemistry from across the table.

Following are a few questions you can ask to bring out your date to open up and connect with you. 

  •   What do you aspire to be ten years from now?
  •   What is one quote you live by?
  •   When was the most fun you had in your life?
  •   Do you have any fears? 
  •   What would you be if you could be anything other than your existing profession?

Questions to Avoid on a First Date Night

Determining what to say during your first date can make you unwillingly say something that you shouldn’t have and regret it later.

For this reason, it is always great to be prepared beforehand. Prepare a few questions beforehand, so you can start a conversation with a new person once you’re seated across from them.

  •   Questioning about the reason behind their last breakup-

I understand that you must be curious to know this, but as much as you want to know, it’s none of your business to ask them for any details about their previous relationship.

  •   Why questions when they express their interests-

It’s normal to have your personal opinions and interests, but it’s not very good to shove your opinions in other people’s faces by asking them why they like pancakes and not eggs in the morning. Or why do you prefer cats over dogs? It makes you come across as rude and creates a judgemental image in front of your date.

  •   Asking out on the first date-

Deciding whether to date a person is a process that may require one to take a few dates or calls to determine. So, asking out your date upfront on your first date can make you look a little pushy and in a rush. First dates should be all about having a good time. Try to keep things light and enjoyable, and don’t take yourself too seriously.

“Relinquish your desire to control the flow of the evening. A sweet and

solid romance is built over time and cannot be rushed. This doesn’t mean you shouldn’t listen to your gut. Your intuition is like a voice whispering in your ear. “ – recommends Laura Doyle

Tips for a First Date

If you’re new to dating or diving in after some time, here are a few tips to keep in mind to help you have a smooth sail through your date and land you on your second date.

  •   Relax, and don’t overthink it.

Whether you’re a newbie or an experienced player in the dating game, you may have many thoughts racing inside your head about your date. When faced with such a situation, tell yourself that it’s only a date where you are supposed to enjoy and be yourself, and even if you mess it up or it doesn’t work out, remember that there’s plenty of fish in the sea.

  •   Be yourself and go with the flow.

If you keep overthinking every minute detail and how you’re supposed to respond to it, you’ll probably be too occupied with giving your best impression, which may hinder you from being your true self. Just know that presenting a perfect and unrealistic impression of yourself can be deceiving for the person and you, too, as you would want a partner that accepts you the way you are, which will only be possible if you present your true self.

  •   Keep a positive exchange of words.

Please don’t hesitate to thank them for showing up, paying the bill, or driving you home. It’s always kind to return a positive gesture by thanking them.

Dating can be a slice of cake and a complex code to crack for some. It has many lessons and takeaways to help you work on yourself. Even if you don’t end up getting into a relationship with your date, stay optimistic for the future, and you will eventually get there.


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