How to Land the First Date
You're busy sifting through the apps. Occasionally swiping right on the profiles you find the most appealing.
Suddenly, your phone buzzes—you have a match! Their profile lists qualities you feel a strong connection to.
It's time to chat.
But you’ve been here before, with mixed results that sent you trying the apps just one more time. How do you continue moving forward in the conversation, potentially setting up a date?
As someone who grew tired of endless conversations that went nowhere, a framework I've enjoyed using is the "three questions and a date" structure. This encourages momentum in the conversation, as well as directs you towards the goal of meeting up in person.
To get the ball rolling, you simply scan through their profile and ask a question about something you've read. Their profile may mention dancing, hiking, or going to concerts. That's all the information you need.
The first actual message you send should mention one of those facts, such as, "What kind of music is your favorite to dance to?" Starting a conversation about their interests will let them know you are serious about getting to know them. After they reply, be sure to acknowledge what they said and mention any strong personal connections. Immediately after, ask your second question, using more information from their profile. For example, if you saw pictures of them skiing, you could ask, “How long have you been mastering the slopes?” or “What is your favorite ski destination?” or even, “If you could go skiing anywhere, where would you choose?
These questions carry the conversation's momentum forward. You don't have to sit awkwardly waiting for their next message, and you will keep them engaged in the conversation
After you have chatted through your first two questions, the third message is when things get exciting. Like messages one and two, you're asking something to keep the conversation going, but this one serves a second purpose.
Let's say you see they like trivia or karaoke—ask them about it, but move beyond it; after all, your end goal is to go on a date with this person, to move out of the digital and into the real world. This is where the Vibe Check comes in.
"I see you really like karaoke; it would be great for us to check it out sometime. Let's grab a coffee first to see if we vibe."
That's where the hook comes in. Most of the time, they'd agree to this brief meetup. This is also the moment to ask for their phone number and take it off the apps. (Except for Hinge, where phone numbers are usually traded after the first date.)
..."Awesome, send me your phone number, and we can set something up."
After you get their phone number, wait about an hour before you reach out. Be direct and immediately mention your plans to meet. For example, "Hey, this is (your name) from Bumble (or Tinder/JDate/etc.). How about we meet on (day) at (specific time)?" It's best to find a coffee shop, or similar, in a neighborhood convenient to your locations—just in case your meetup goes well enough to warrant a second locale.
Once you send this message out, it's highly likely you'll get a response, and you can set up your first date. Dating apps can feel endless, but having a structure like ‘three questions and a date’ gives you a clear path forward. Remember, the goal isn’t to keep chatting forever—it’s to meet in person and see if there’s a real spark. Even if every match doesn’t turn into a date, practicing this approach will help you build confidence, connection, and momentum.