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Beyond Small Talk: 25 Questions to Build Real Connection in Dating
By Phoebe Rogers, Clinical Psychologist specialising in Dating & Relationships
Struggling to move beyond small talk?
It's so common to feel hesitant about getting close in dating. Maybe you’ve been hurt before—rejected, abandoned, or ghosted, and so you're now guarded.
Opening up feels like a risk, and you worry about getting hurt all over again. Or, as one client said, what if I share something vulnerable and personal, and they use it against me or have false intentions?
It's all about learning to watch out for the signs, and listening to your nervous system (I explain more about red flags and how they feel here). As I explained to her, the only way you know that you can truly trust another is by observing their response (over and over again) when you share something vulnerable.
So, the truth is: true connection starts with vulnerability. A willingness to be open, human, real, and authentic.
Connection is built step by step, through gentle self-disclosures met with understanding and reciprocity. It’s about sharing a little bit at a time and seeing how it’s received. Does your date share back? Are they interested in getting to know the real you?
When both people feel seen and valued, that’s where trust begins to grow. I shared a post recently on Instagram about connection building in dating and it got a huge response (you can see the post here). The post included 25 Questions to build real connection in dating.
What I realised is that many of you want help and support with how to actually build connection in dating; what is too much, too vulnerable, too curious? The truth is, nothing will be too much for the right person, and asking allows you to see their level of emotional openness, vulnerability and maturity.
Here’s the complete list of 25 questions to get to know your date and build connection:
What’s one thing you can’t live without and why?
What’s your best relationship quality?
What’s a self-care non-negotiable?
How do you feel about dating at the moment?
I loved this part of your profile, tell me more about it.
What’s your best and worst quality?
What has been the biggest life lesson for you?
What’s your overall philosophy on life?
What do you most want to achieve in the next 5 years?
How does fun have a place in your life?
What’s a strong value of yours?
What brings you the most joy in life?
What’s something you’re passionate about that you could talk about for hours?
If you could live anywhere in the world, where would it be and why?
What does emotional security mean to you in a relationship?
What’s a book, movie, or show that’s had a big impact on your life?
If you could master any new skill instantly, what would it be?
How do you typically deal with conflict or disagreement?
What’s your favourite way to spend a day off?
What’s the best piece of advice you’ve ever received?
If you had to describe yourself in three words, what would they be?
What do you value most in friendships?
How do you recharge when you’re feeling overwhelmed or stressed?
If money was no object, what would you do with your time?
What does vulnerability look like to you in a relationship?
These questions encourage meaningful conversation and connection, perfect for sparking deeper connections in dating. I'd love to know how these questions have worked for you.
Now is the perfect time of year to be dating, the weather is warm, people are happy, Sydney is looking beautiful; there's a certain energy in the air. So, if dating is something you're thinking of doing, now is the time.
Please also note that my books are filling up for the end of 2024, so if you're wanting to work together, please get in touch to secure your spot.
You can contact me here to explore working together to help you find love now.
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