Best Questions to Ask in Online Dating Messages

Today we’re going to talk about the best questions to ask in online dating, plus why you should be asking questions at all. As a dating coach, if I could only give ONE piece of online dating advice for the rest of my life, it would be this. ASK! QUESTIONS!

Why? They show you’re interested in the other person. They show you’re a generous conversationalist. And the biggest thing, when you’re still chatting in the apps – it gives the other person the easiest way to respond to you and to keep that conversation flowing. 

Best questions to ask in online dating:

Actually ask questions!

Each time you message someone on a dating app, my cardinal rule is: always end with a question. You’re making it clear you want the conversation to continue, and you’re giving the person the easiest way to continue it!

What are my other tenets of question asking? Read on!

Be specific!

Avoid generic or overly open-ended questions. It’s a lot easier and more interesting for someone to answer your question “What’s the last song that got stuck in your head?” than “What kind of music do you listen to?” Asking a question that leads to a specific answer takes the burden off of the other person – they don’t have to sit and think about the million different paths they could take to answer your question, you’ve already laid out the course for them. The less mental work the other person has to do, the more quickly they’ll respond.

Be creative!

People also LOVE answering questions they haven’t heard before so that they’re not stuck giving the same answer they’ve already given a hundred times to the same question. The easiest way to do this? Have your own rolodex of interesting, engaging, out-of-the-box questions that you can ask anyone.

“If there was going to be a movie about your life, would you rather it be a “based on a true story” Hollywood biopic, or a super-realistic documentary?”

“What’s your “lame superpower,” as I like to call it? For example, I can always eyeball exactly which size of Tupperware is needed for leftovers.”

Write yourself an actual list of fun, thought-provoking, lighthearted questions. Think through funny late-night dinner conversations you’ve had with your friends, cute and weird things your kids have wondered aloud, or just what quirky topics have always struck your fancy. Keep a running list on your phone so you can add to it whenever you’re inspired.

Want some help? I’ve got 30 great starter questions for you.

Stand out from the crowd!

As I mentioned, people ask a lot of the same questions on any given profile. If someone’s profile talks about how they run a lot of marathons, then you better believe they are fielding a LOT of generic questions like “How many marathons have you run?” “What was your favorite marathon?” “When did you start running marathons?”

I challenge you to put in the extra effort to stand out from the crowd. Think about what kinds of questions the person is probably getting all the time, and then go deeper.

“What were the best and worst foods you’ve eaten the night before a marathon?”

“What’s the one song that really helps you push through Mile 18?”

“What are your immediate-post-marathon traditions?”

Another option? Look for hidden gems in the person’s profile. That person who’s wearing a funny outfit way in the background of one of their photos? Ask about him. There’s a photo in their kitchen? Ask where they got the recipe for whatever they were cooking and how it turned out, out of 10 stars.

Going the extra mile to ask a question that’s fun to answer is going to get you so many more responses. It’s worth it!

Here are your next steps:

  1. Brainstorm your list of compelling questions, and write them out in a note on your phone so they’re easy to access
  2. Read my blog about 30 Conversation Starters on Hinge that Actually Work
  3. Set yourself up for messaging success by downloading the tip sheets included in Profile in an Hour (including all the quirky questions I’ve written and used!)
  4. Ask a million questions of your matches!

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Hi! I’m Alyssa Dineen and I’m a personal stylist and dating coach all rolled into one. I started Style My Profile to help other online daters feel better about getting out there— and staying out there— in the world of online dating. Whether it’s to meet your soulmate, to find a fun person to have dinner with or even just match with more people, I can help you from the ground up.


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Purchase our Profile In An Hour, designed for getting your profile swipe-right ready in as little time as possible.

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