20 Essential Online Dating Questions to Ask a Match

Getting to know someone on-screen can be challenging, that’s why having some go-to online dating questions is key. 

Before you meet a match in person, it’s important to read their profile, exchange messages and maybe even have a video call. 

However, maintaining great conversation when you’ve never met someone can feel nerve-wracking, and that’s where these questions come in. 

We’ve rounded up our favorite online dating questions for you to ask your matches.

The Online Dating Questions You Need to Know

Introductory Questions

Let’s start with the basics. These simple, surface-level questions are great opening lines for when you’re dating over 50. They set a casual and easygoing tone for the conversation.

Don’t feel pressured to ask super interesting questions yet, simply think of what you would ask someone at a dinner party or what small talk you’d make at a work event and go with that. You can get more creative in a minute.

Some of this information might be on their profile, so be sure to give it a read first. These types of introductory questions include:

1. Where are you from?

2. Where do you live now?

3. How old are you?

4. What do you do for work?

5. How do you spend your free time?

Fun Questions

Every conversation, even the most engaging ones, hit a lull at some point. So if you experience an awkward silence or two, don’t worry. It’s totally normal! 

When you feel things start to stall and you aren’t sure what to say next, ask some lighthearted online dating questions to keep the dialogue going. 

These examples are easy to answer, give you a lot to talk about, and have the potential to keep you messaging for hours. 

Before you know it, you’ll be engaging in a friendly debate about sports or sharing your most embarrassing moment from middle school. 

6. What’s your favorite book, movie, or TV show?

7. If you could live anywhere, where would you choose?

8. Would you rather an active holiday or a one by the beach?

9. What was your first job?

10. If you could be a character from any film, TV show, or book, who would you be?

Relationship Questions

Now that you’ve got the conversation going, feel free to dive in and talk about dating. After all, it’s why you’re here! 

You might feel like these questions are too forward, and under other circumstances, they might be, but remember, you’re on a dating app. 

Everyone here is looking for companionship and if you’re hoping to meet someone you click with, these online dating questions are important. 

The answers to these questions will reveal a lot about your compatibility with someone and will help you determine if you’re interested in pursuing them further.

If you’re looking for long-lasting love and they’re looking for something more casual, now is the time to get that out in the open. 

11. What are you looking for in a partner?

12. What’s your idea of a perfect first date?

13. What has your experience with online dating been like?

14. What made you want to talk to me?

15. Do you have any deal breakers?

Personal Questions

If all is going well and you’re having a nice time exchanging messages, then great! This is a sign that you can ask them something a bit more personal about themselves, something they probably didn’t mention in their profile. 

Remember to be polite and respect their boundaries. If they seem uncomfortable with any of your questions or hesitant to answer honestly, drop it and move on.

Taking note of your matches behavior like this is key to successful online dating in your 50s.

If you continue chatting, they might choose to open up to you in the future. 

16. Have you ever been married before?

17. Do you have any children or grandchildren?

18. What’s your biggest fear?

19. Are you an introvert or an extrovert?

20. Why did your last relationship end?

Questions are a fantastic way to get to know someone because they spark natural conversation. So, avoid asking these questions one after the other and instead ask them one at a time. Listen carefully to your matches’ answers. 

Pay attention to how much you’re speaking too – nobody likes a conversation hog. If you notice that you’re doing all the talking, hold off a little and give them space to talk.

If something they say leads the conversation elsewhere, that’s perfect! Don’t feel like you have to stick to this list, sometimes a little improv goes a long way. 

So next time you feel like striking up a conversation with one of your matches, keep these online dating questions close by.