Have you ever left a date feeling… well, nothing?
It wasn’t even a bad date, but the conversation never seemed to go deeper than surface-level. Yes they were funny. Yes you got on okay. But when you left the bar, you had no real sense of who that person was.It’s classic for daters to default to vague topics that feel safe. But in doing so, they miss their prime opportunity to uncover their date’s core values, emotional availability, and ultimately their compatibility.
But with a few simple techniques borrowed from psychology, you can communicate with intention, build connection, and cut through the pleasantries to unearth what really makes your date tick.
The deep questions do matter
When I advise clients to delve deeper into the conversation with their date, some shudder at the very thought: “But that’s so intense!”
Not necessarily. Not if you do it tactfully, and in the context of an already meaningful conversation. Think of it this way: dating isn’t really about whether you find the person physically attractive; you know that faster than your brain can process it! No, dating is about discerning whether your lives, goals and values could truly intertwine.
Surface-level questions are fine at the early stages; in fact they’re still vital, of course. But asking “Do you like to travel?” or “Where did you grow up?” may only get you so far. To unlock genuine compatibility, you need to probe deeper into your date’s inner world: their beliefs, their past experiences, their emotional landscape.
“Like an interrogation?” some of my clients respond. Nope, not like an interrogation! Like someone with intelligent curiosity, who’s ready to foster a space in which real romance can flourish.
Communication that works for both of you
Knowing your attachment style helps you understand how you seek and receive connection, so you can learn to observe patterns within yourself rather than simply reacting to what happens across your dating journey.
What’s more, knowing the telltale signs of each attachment style can give you a better grasp on your date’s psychology, and help you tailor your communication accordingly.
- Secure individuals tend to communicate directly and openly. They’re comfortable with both closeness and independence. They’re likely to respond to questions with interest and reciprocity.
- Anxious individuals may seek reassurance and intense closeness at an unusually fast pace. Their questions might probe for commitment or fear of abandonment. In response, you should ensure to offer consistency, but without overpromising.
- Avoidant individuals sometimes shy away from emotional depth, preferring practical or intellectual topics. They may answer questions vaguely, or deflect them altogether. If this is the case with your date, you may wish to gently create a space in which they can be vulnerable, without pushing too hard.
Understanding this fundamental psychological framework will help you interpret your date’s responses more effectively—and enable you to reflect on your own behaviour, too.
Do you know the most powerful type of question?
Yes, really. Having helped thousands of singles find love, what I’ve found is this:
The most powerful type of question on a date is both open-ended and values-based.
Closed questions are fact-based and elicit a simple yes or no. They’re handy for kicking off a conversation, but then you need to pivot to open-ended prompts that encourage reflection and reveal your date’s deeply held principles. Rather than focusing on superficial preferences, try to understand your date’s internal processing. How do they think? How do they approach challenges?
Understand their relational blueprints:
- “Do you get along with your family?”
- “What role would you say your family’s played in shaping who you are?”
Invite your date to share their passions, and what energises them:
- “What do you do for fun?”
- “What makes you feel alive?”
- “What makes you feel most like yourself?”
Explore their capacity and curiosity for growth:
- “Where do you like going on holiday?”