Already have an account?
Get back to the

Going on a First Date? These 24 Questions and Topics Will Keep the Conversation Flowing

These dating tips are perfect for mature singles.


This ones for all the single ladies. To quote Beyonce, “Put your hands up!” Whether you’re dating regularly or getting back in the game after a lengthy hiatus, congratulations! This must be said first and foremost. Why? Because it takes guts to put yourself out there. The risk, however, is worth the reward. 

So let’s talk first dates. The first date is important (obviously) because it shapes your impression of your date and is the time when you both decide if there’s sufficient chemistry to have a second date. A first date can be fun, or it can be awkward — though even the best ones are often a combination of both. Having a few go-to questions on hand can help to fill awkward silences, while following a few simple rules can help you avoid them entirely. 

Below are dating tips and situational advice for mature singles (although they actually apply to anyone — young or old — who’s dating). 

What is good advice for mature daters on first dates?

Let’s start with a question: What exactly is “mature dating?” Answer: It’s the same as any other dating – two people, each seeking a partner with whom they share interests, values, and beliefs – except those engaged in it are over 40. And just like with any other dating, mature dating can, on occasion, be awkward. With this in mind, below are some tips for getting your first date conversation going.

Avoid awkward silence with ice breakers

One of the simplest ways to spark conversation is with lighthearted questions and conversation starters. Ask questions that make you and your date comfortable and get them talking about topics they enjoy. For instance, first date conversation starters like “What type of music do you listen to?” or “What do you do for fun on the weekends?” are good jumping-off points for more meaningful conversations. Don’t forget, too, that you’re meant to participate in the conversation as well — versus asking all the questions, which can feel like an interrogation to your date. When meeting someone for the first time, don’t forget to offer up details about your life and interests. Tell your date about your dream job, the destinations on your bucket list, or your favorite books and TV shows. Doing this can shift small talk toward richer interactions, thus shifting the date seated across from you to a potential partner.

Get personal 

Once things start flowing and there are fewer lulls in the conversation, steer away from surface-level dialogue and, instead, delve into deeper topics. This gives both parties a a chance to share more personal stories and experiences. For instance, asking follow-up questions like “Why was that the favorite place you ever visited?” or “What do you do when you’re spending time with your best friends?” encourages thoughtful responses that paint a picture of your date’s life. 

That said, always remember to respect boundaries — if someone doesn’t want to share something personal, don’t push them for an answer. It’s better to make a positive first impression than dig for intimate information. Some discussions, like pet peeves, the last time you went on a date, or your relationship red flags and deal breakers, should wait for the second date. 

Make connections 

Follow-up questions that connect back to previous discussions show your date that your listening intently. They also help keep the conversation flowing without feeling forced, and encourage dialogue other than talking about topical subjects like the weather and pop culture. If, for example, your date says they love hiking or listening to podcasts, ask what their favorite trails are, which parks they’ve visited recently, or what podcast apps you should download. These types of follow-up inquiries show genuine interest in what they’ve shared with you so far.

What are useful topics to explore on a first date?

When it comes to more mature dating, whether in your forties or in your golden years, finding interesting topics that don’t open either party up to too much intimacy right away can be challenging. Unlike dating in your youth, you’ve both lived long enough to have experienced life’s ups and downs. Sharing the latter too soon is a definite no-no. You also want to avoid discussing anything too controversial. (Think politics and religion.) 

That doesn’t mean, though, that you can’t talk about anything substantive. Rather, it means you must ask the right questions. Doing so ensures you get to know your date (and they can get to know you) without touching on sensitive topics. Below are examples of good first date fodder for people over 40.

Family and Friends

Discussing family and friends is an excellent way to open up conversations. Ask your date about siblings and other family members, and talk about the people you hang out with regularly. This gives you insight to their social circle, sense of humor, and favorite things.

Hobbies and Interests 

Typically, the fact of having lived a bit longer means that mature daters have a cadre of hobbies and interests. Do both of you enjoy reading? What kind of books? Maybe one or both of you have a passion for gardening or cooking. Open-ended questions spark natural discussions that allow you to  learn more about each other’s interests. Bonus: you’ll have plenty of ideas for future dates. 

Current Events and News

In addition to discussing hobbies, interests, and long-term goals, talking about current events is another way to get to know one another better. Whether it’s national news or international affairs, asking your date which topics they follow can give you a glimpse into their values and views on the world at large. If it happens that you both follow similar stories and news outlets, you’ll have material for further discussion. 

Be warned, however, that asking what they follow is quite different from asking how they feel about what they follow. In today’s divisive world, unless it’s clear you share the same views, it’s best to avoid political conversations. 

Your Professional Lives 

Careers comprise such a large part of our lives that it makes sense to at least touch on them on a first date. Ask your date what led them to their current job or career path — this could open up interesting conversations about goals, aspirations, and values, and give you a sense of their disposition as relates to their work and satisfaction.  

Travel and Culture 

Travel stories and cultural discussions provide the creative-meets-cerebral conversation that mature daters crave. Instead of simply asking, “Where have you been?” try something like, “What was the most interesting place you’ve ever visited?” Framing your question this way adds an opinion element to the answer, which in turn, lets your date share ideas versus lists and lets you glean insights about their interests and adventurousness.   

Goals and Dreams

Talking about long-term plans and life aspirations can feel overly serious, but if approached lightheartedly, can help you gain insight into each other’s values and beliefs. 

What are the best questions to ask on a first date?

Not all questions are created equal. On a first date, some will spark stimulating discussion; others will drive to a dead end. Here are a few examples of the former — questions that delve deeper and yield conversation that flows naturally.

General Questions

  • What are your favorite hobbies?
  • What do you like to do for fun?
  • What did you do last weekend?
  • What do you like about living in [city/area]? 
  • What do you like doing in your free time?  
  • What was the best trip you’ve ever taken? 
  • How did you get interested in [hobby/interest]?  
  • Are there any books or movies that have really appealed to you lately?  
  • What made you decide on this restaurant tonight?  
  • What do you think makes this city unique compared with others?
  • What are some of the funniest and most embarrassing things you remember from your childhood or teenage years?
  • Do friends often come over for dinner parties at your place? 
  • Do you have any favorite memories from recent trips or events that stand out for you?

These questions are great starting points because they’re general enough to ask anyone but specific enough to generate in-depth conversations if the other person is willing to share.

Questions To Connect on a Deeper Level

  • What motivates you?
  • What is something that you’ve done that you’re proud of?
  • What do you value in life?
  • Who are some people who have been influential in your life?
  • Have there been any interesting changes in your life recently?  
  • If money wasn’t an issue, what would be something fun that you would love to try out one day soon? 
  • What’s one thing that makes you feel happiest?
  • What is the most meaningful experience of your life so far?
  • If you could make one change in the world, what would it be?
  • How do you like to spend time with your loved ones?
  • What values do you think are important in a relationship?

These questions delve deeper into the other person’s unique drives and desires, and provide insight into what they prioritize in life. The answers they yield can give you a glimpse of who your date is beneath the curated first impression.

The Last Word on First Dates

Ultimately, good conversation requires that both parties are open and honest with each other. A successful date night is one wherein both people learn equally about the other — and hopefully, find common ground and mutual interests. While dating may seem scary at first, it doesn’t have to be difficult. Just remember to stay curious and listen. You’ve got this.

Use left and right arrow keys to navigate between menu items. Use right arrow key to move into submenus. Use escape to exit the menu. Use up and down arrow keys to explore. Use left arrow key to move back to the parent list.