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16 Fun, Flirty, & Deep Questions To Move From The Apps To An Actual Date

August 30, 2023
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questions to ask on a dating app
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August 30, 2023
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Online dating can be frustrating, but it's supposed to make things easier. Dating apps provide you with an abundance of options and the ability to meet potential matches from the comfort of your own home. Learning what questions to ask on a dating app helps set the tone for good conversation and a stronger connection.

Whether you're looking for opening questions on Bumble, flirty questions to ask on Tinder, or deep questions to unearth potential red flags with online dating, there are many ways to avoid the same redundant conversations (or worse, getting stuck in the "pen pal" stage).

Psychotherapist Kelly Scott, LMHC, dating coach Blaine Anderson, and therapist LaTonya Washington, LICSW, weighed in on the best questions to ask and how to keep the conversation going on a dating app. Use these questions to build a deeper connection and get off the apps and onto a date.

How to use dating apps more intentionally

First things first: Anderson recommends investing time and energy into curating a great profile that's reflective of you and your interests. “Most people rush through creating a profile to get to swiping ASAP,” she says. “You want to be strategic about what you share—every photo and word matters.” 

While, yes, you want to create a profile that accurately portrays your unique personality, Washington urges people to be clear about what they’re looking for.

“Some women avoid saying they’re looking for a relationship because they don’t want to scare people off,” she says. “This can be misleading and lead you to connections that aren’t what you’re looking for, rather than if you were more upfront in the beginning.” 

When you date with intention, the goal isn’t to engage with as many people as possible; it’s to engage with the right people who are aligned with your dating goals.

Questions to ask on a dating app

  1. What’s an attribute or body part that you get lots of compliments on? A more flirty question to ask on a dating app, Washington recommends this one if you’re looking for something a bit more casual or for just a hookup.
  2. What is your favorite non-sexual way of being touched? Another flirty question recommendation by Washington, this is a great way to get flirtatious without being overtly sexual.
  3. What is something that turns you on that most people would be surprised to know about? This flirty and sexual question is also great if you’re just looking for something more casual, says Washington. It’s also a great way to learn something more unique about them.
  4. Who is someone in your life who has inspired you? It can be hard to think of deep questions for online dating that don’t come off as invasive, but Washington recommends this one, since it’s pretty open-ended yet personal. You’ll likely learn a lot about their values by finding out what inspires them.
  5. How do you deal with disappointments in relationships? Washington loves this question because it can give you insight into how a person may deal with challenges in relationships. “It’s important to know how people deal with disappointments and challenges, and if they’re able to talk about them,” she says. “You want to know they are able to show vulnerability and handle disagreements in relationships.”
  6. What’s your vision for a relationship? This is a great question to ask someone online to really get to know them. Washington adds that it can tell you if they envision marriage, a long-term committed relationship, or maybe even something non-traditional.
  7. What are things you aspire to have in a relationship with a person? Purposefully open-ended, Washington recommends this deeper question, because it can get you to understand what someone’s priorities are and if you feel like you are aligned with them.
  8. Do you have a couple in mind as your relationship role model? You may learn that they’re ideal relationship lines up with what you’re looking for. Alternatively, Washington says that from this question, you may also learn that they haven’t actually seen good examples of healthy relationships. While it’s not a deal breaker, it may mean that they struggle to understand what a healthy relationship is.
  9. When you were a kid, was there a character from a book or movie that you would fantasize about being? This is a funny question that Washington recommends, but it can also provide some interesting insight and facilitate a fun, lighthearted conversation in which you can learn a bit more about their childhood or dreams.
  10. Tell me something about your hometown that I wouldn’t know as an outsider. When thinking of questions to ask someone online to get to know them, Washington recommends simply asking questions that you would ask if you met them in real life. Asking about someone’s hometown is always easy, and they’ll always have lots to open up about.
  11. What would your best friend say is your best quality? This one may teach you a bit about what they think of themselves, and how they feel others perceive them. It’s a light-hearted question that could end up revealing a bit more than you may expect.
  12. What would the people closest to you say is your most annoying quality?This is a great way to see how self-aware someone is. It’s a funny question, but you may wind up learning something interesting about them. For example, if they say it’s that they are bad at communication, that’s probably an indication that they may not be ready for something serious.
  13. What’s the last book you read (or television show you watched) and what was your biggest takeaway from it? A great way to get to know someone, you’ll learn a bit about their taste as well as how they process information. Maybe you’ll learn that they’re a deep thinker or that they like to keep life a bit more light-hearted.
  14. I can already tell we’re the perfect match because you like museums (insert whatever your common interest may be here). Where should we go for our honeymoon?Anderson suggests this flirty question. It can help keep the tone light and less formal, if that’s what you prefer.
  15. What do you like most about yourself? Don’t judge this short question by its length. Anderson suggests you can get a lot of depth out of someone from it.
  16. Would you like to go out sometime? Yup, we had to include this one here. You may be wondering how to keep a conversation going on a dating app, but Anderson recommends that you actually just don’t. Go on a date in real life sooner rather than later—that’s the best way to really learn about someone and to see if you’re compatible.

Red flags with online dating

Everyone has their own red flags to look out for when online dating.

Anderson and Washington both recommend staying away from matches who only want to be your penpal. Anyone who has spent time on a dating app can relate to the experience of talking to someone for weeks, without ever going out on a date.

“If you sense they’re avoiding a date, they’re not the one,” Anderson emphasizes. 

Per Washington, another potential red flag is someone who uses their profile to express the things they don’t want.

“This can be an indication that they dated someone with those attributes, and haven’t healed from that yet,” she explains. “It can also mean they’re not clear about the things that they do want.”

Scott says some people tend to jump to red flags too quickly. “Aside from some people being openly unkind, nasty, or hostile, dating is a lot about asking yourself how someone is making you feel,” she says. “If someone makes you feel lonely or anxious, that’s an opportunity to ask yourself if that’s a reflection of yourself, or of that person.”

Scott adds that oftentimes there can be a temptation to make how you’re feeling about the other person. Instead, she suggests using your feelings as an opportunity to look inward and reflect about your needs.

How to keep the conversation going on a dating app

As Anderson pointed out, you really don’t want to keep the conversation going on a dating app for very long.

But when you are chatting on the apps, make sure to ask questions and go beyond surface level.

Washington recommends going deeper than just asking someone how they’re doing or how their day is going. “Get a bit more specific by asking them what the best thing that happened in their day was, if they have any trips planned, or about the most recent vacation they took,” she suggests.

That said, Washington agrees that the goal should be to move off the app. If you’re not quite ready for that, most apps have the option to do a phone call or video chat, which can perhaps make you feel more comfortable before meeting in real life.

“As a rule of thumb, I’d say it’s not advisable to communicate for more than a week on a dating app,” Washington says.

How dating impacts longevity

“There are countless studies on how loneliness leads to negative health outcomes,” Anderson says, noting that dating is great for longevity.

Washington adds that we need human connection and intimacy for our health and well-being, whether that’s in a long-term relationship or marriage. 

One caveat, per Washington, is that casual dating and the early stages of getting to know someone can be stressful. Be sure to think carefully about the interactions that leave you feeling good, versus those that leave you feeling stressed.


How do you answer “What are you looking for?”

Washington says it’s best to be authentic and honest when answering this question. Don’t be afraid to be honest about whether you’re seeking a casual hookup or serious relationship.

What questions are best to ask on Bumble?

You can ask any of the questions above on any platform, but since Bumble asks women to initiate the conversation, Anderson suggests asking “Know what I love about your profile?” She finds this to be a great lead-in to a bigger conversation—and you’ll likely always get a unique response.

What are some red flags with online dating?

Look out for people who are openly hostile or unkind, or who use pictures that may appear altered. Find additional red flags to look out for above.

The takeaway

Conversations on dating apps can feel a little monotonous. Having a handful of deep, flirty, or funny questions on hand is a great way to mix things up and get to know someone better. It may even lead to you having more fun on dating apps and, ultimately, getting out in real life. If you’re interested in building deeper connections, check out our curated list of the best dating apps for serious relationships.