Dating Made Easy: What To Talk About On A First Date

Updated January 19, 2023by ReGain Editorial Team

Dating and relationships come with a category of responsibilities. It can be as challenging as it is rewarding to date in today's society. One of the biggest obstacles in both dating and relationships is the communication factor. Many relationships face hardships because one or both parties don't communicate the best they can.

Nervous About A First Date? Want To Discuss Something Else?

The onset of poor communication is sometimes established at the start of the relationship. It all starts with making plans for a first date and usually continues throughout the dating relationship. Many people are afraid that they'll say the wrong thing or approach an uncomfortable topic with their date. The plan to keep the conversation light can lead to months of conversation that have very little substance. It is important for dating to be fun, relaxing and present an opportunity to engage in quality conversations. If you struggle with dating issues such as difficulty communicating with your partner or knowing what to talk about, there are a few ice breakers that could help you get through the first date without sitting in silence.

The Conversation

A first date can be awkward, but there are steps you can take to make it less awkward or prevent it from turning into an awkward date. Set the tone for the date to allow you both to be comfortable or relaxed while around each other. If the two of you are in sync with each other, there may already be a sense of comfort with each other. Offer compliments but try not to overdo it instead of keeping the compliments sincere.

It is not best to bring up or discuss things like political issues on the first date, as these types of topics can create a divide between you and your date. It is okay to engage in conversation that addresses any concerns that they may have about the date itself. A quality conversation maintains a consistent flow without awkward pauses. You can't always prevent this, but talking about certain topics can help minimize those silences.

Ask the Right Questions

A first date is best when it doesn't feel like a job interview. It is a good opportunity to get to know someone better and decide if you would like to pursue a second date. Some questions can appear or sound rude, and others can feel a bit out of place. Sometimes, to get to know someone, it is best to ask questions that allow you to see how they think or hold their priorities in life. This can be accomplished by asking tactful, indirect questions like the ones below.

Here are a few first date tips and questions to ask:

1. Where Would You Go Right Now If You Could Travel Anywhere in The World?

Pay attention to your date's response. If they reply, "nowhere," it could be a long and possibly boring first date. Try not to take it personally, it's not you, but they're either not into the date or closed off, which could make getting to know them a challenge.

2. What's the One Thing That I'd Never Guess or Assume About You?

This question is a curiosity trigger and can sometimes bring out the inner flirt in your date if there is one. Based on their answer, you can determine a little more about their likes, dislikes, and personality.

3. What Career or Job Have You Always Dreamed of Pursuing?

This is the best way to ask your date what they do because it narrows the window for them to give a one-word answer. For instance, you may ask what your date does for a living, and they may respond by saying, "I'm a nurse," "I'm a teacher," or "I'm an account executive." However, asking about their dream job or career may lead them to elaborate more on what they currently do and their current career goals. This question can help you see or understand your date's values and qualities and if they're aligned with your own.

4. What Do You Like Most About This City?

This is a great question that can lead to several other conversation topics. You'll learn what their interests are and how they like spending their time. It helps you discover what things, if any, that the two of you have in common. This question establishes the groundwork for planning the next date if you are both interested in each other.

5. What Is Your Favorite Sport and Team?

If you enjoy Monday night football or NBA finals and your date has no clue what team plays in either sport, it is important to ask yourself if you'll devote enough time to dating and not allow your sports interests to consume or destroy the relationship. There are ways to balance both.

Avoid these 3 questions or topics on a first date:

1. Don't Ask About Their Parents, Families or Friends

A first date is an opportunity to get to know your date on the surface. It's not an invitation to pry into all the details of their personal life. Make an effort to keep all conversation topics away from anything that requires your date to talk about topics that may be uncomfortable.

2. Don't Ask Questions About Their Ex

You probably already know this but asking about the ex is off-limits. It runs the risk that you may open up old wounds, make them think about their ex, or bring up negative feelings that may ruin your date. Most people don't want to spend their first date talking about previous relationships. It's also a chance that they won't be completely upfront with you about what happened with their ex. They don't know you well enough to bring you into that area of their life yet. Also, there is no real need to know what happened with the first relationship. Your approach may bring out something in them that they have never experienced.

3. Don't Ask Judgmental Questions or Make Judgmental Statements

Avoid making critical comments about your date's hobbies or career choice. Be sure to avoid saying things like, "I could never work in that field" or "Why don't you try a different career." These types of statements could lead your date to believe that you're judgmental or critical of their career choices. Always offer commendations on whatever career choice they've made and encourage them if they express a desire to achieve more.

First Date Topics of Conversation

Most experts agree that first dates go great when the female is allowed to talk about herself. It allows for a better connection, and the overall experience is more memorable. However, nobody wants to spend the entire date talking about themselves or listening to someone else talk about themselves. There are other topics to discuss on a first date, other than yourself or your date. Here are several other topics to consider.

Favorite Foods or Most Memorable Meal

This expands the possibilities of the "what's your favorite food" question and opens the door for a more detailed conversation. Your date will likely be detailed in describing the meal experience and also provide some insight into their favorite foods, allergies, and favorite places to eat.


This topic may generate answers like painting, playing guitar, racing, or many more, but the answers may be a bit deeper and give you a little peek into their personal life if there is already a connection forming. The answer will show you a little more about the things your date enjoys, feels confident about, and will most likely gravitate towards in a relationship. They can also be ideal for incorporating in future dates if things go well.


This is an elaboration of the favorite music, artist, or song topic. People tend to paint more visual images when they are asked to recall a certain time or event. Again, asking your date directly what their favorite song or music genre is could result in a simple or single-word answer. Even if your date has never attended a concert, they will likely express which artist they would have enjoyed or the artist or group they'd love to see in concert.


This is a great topic for a couple of reasons. It allows you to learn if your date likes or dislikes animals like cats or dogs. Some people are deathly afraid of one or both, and this could present challenges if you're a cat lover with four cats in your home. You may also find out if your date has allergies to certain kinds of animal hair during this conversation.

Nervous About A First Date? Want To Discuss Something Else?

Places They Have Lived

This topic sparks conversation about your date's life in ways you wouldn't imagine. They may expand their answer to elaborate on places they lived in school or the military. It could also prompt an answer that reveals how they ended up in that city or if they plan on being there for the rest of their life. This topic has loads of energy and great potential to learn more about your mate.

Places They Love to go to Relax

Asking about places your date loves will give you an idea of what your date considers to be a relaxing vacation. If you listen carefully, you'll likely hear them mention their favorite beach or mountain top. This topic can also show how active and adventurous or, instead, how inactive and calm your date prefers to be when they think of relaxing.

Set Reasonable Expectations

Always set reasonable expectations for first dates and every other date that follows. Don't go into the date expecting to know if this is the person you'll spend the rest of your life with. The first date may reveal that this is not someone you wish to date at all, but it won't reveal enough for you to make long-term life decisions.

It is best not to overthink things when on a first date. Avoid trying to determine what your date thinks of you. Often, you may misread the signs that a person is giving off, leading you to draw the wrong conclusions.

Instead, try going into the first date, expecting to engage in quality conversation, enjoy a nice meal or cup of coffee, and perhaps learn a little more about yourself. Dating has a way of showing opening people up to a side of themselves which could motivate them to be open to new opportunities and adventures. Approach your next first date with a positive mindset and realistic expectations.

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