First dates can go one of two ways. Either you connect so naturally that you lose track of time, or you’re awkwardly watching the ice in your drink melt.
What’s the difference between the two, you ask? A good conversation.
If you want to connect with someone, you need to ask the kind of questions that reveal personality, values, and emotions without making it feel like an interrogation.
Whether you’re meeting someone from an app or trying out dating for the first time, here are some meaningful questions you can ask.
What’s Something You’re Excited About?
This one is great because it’s open-ended, but also positive. You get to learn about their hobbies, passions, or even just how they’re really looking forward to an upcoming concert.
It also gives you insight into what they really enjoy doing, which is way more effective than asking, “So… what do you do?” It’s a great way to keep the conversation interesting and insightful.
What’s Your Version of a Perfect Day?
If you want to understand someone’s vibe without directly asking, this is what you ask. Their ideal day says a lot about their energy level, lifestyle, and personality.
And if you’re doing something fast-paced like speed dating, this question can help move past the small talk and into something more engaging right away.
What Do You Value Most in a Relationship?
This question lets you see how someone approaches relationships and what they’re looking for.
It could be:
- Emotional availability
- Communication
- Shared humour or interests
You don’t have to agree on everything, but alignment here is key if you’re hoping for something more than just a superficial relationship.
Who Has Shaped Your Personality the Most?
It could be a parent, a mentor, or a teacher. This question can bring out stories that are deeply personal, but not too intense. Plus, it shows you who and what they admire, which says a lot about their character.
What’s Something People Misunderstand About You?
This one gives the other person the space to be real. Maybe they’ll tell you how they always appear serious but are a fun person in reality, or that others think they’re an extrovert when they’re really not.
This kind of honesty builds a connection that small talk can’t.
What Do You Think Makes a Relationship Last?
Their answer to this can reveal what they believe works (or doesn’t) in a relationship. Whether that’s teamwork, shared goals, growth, or just laughing a lot.
This question is great for situations where you’re trying to figure out if you both would be compatible for the long term in a short window.
If You Could Live Anywhere, Where Would It Be?
This question can tell you about their dreams, goals, cultural interests, and even their energy and personality.
Someone who answers “Tokyo” is probably different from someone who says “a quiet cabin in the woods” for obvious reasons. It also reveals whether your idea of fun is aligned, without asking if you two could get along on a vacation.
