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

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).

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.” 

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.”

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.

“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.