Curated Questions: Conversations Celebrating the Power of Questions! Intentionally Cracking Love's Enigma Through Analytics | Tim Molnar #30
"The better question is, how am I feeling in my body at the end of or during this date? Do I feel safe? Do I feel seen? Am I energized?" - Tim Molnar
Tim Molnar isn't your typical dating coach—he's a fascinating blend of academic researcher and practical relationship strategist who's transformed how we think about finding love.
As a former Fulbright fellow with both a J.D. and Ph.D. from the University of Colorado, Tim brings analytical precision to the often chaotic world of modern dating. But what sets him apart is how he turned his own dating struggles into a systematic approach that works. After documenting his journey through 47 first dates and meticulously tracking what did and didn't work, Tim discovered patterns that became the foundation for his book, Date Smarter: A Strategic Guide for Navigating Modern Romance.
What I find most compelling about Tim's work is his emphasis on asking better questions—both of ourselves and potential partners, to create more meaningful connections. He challenges us to move beyond superficial interactions and app-swiping fatigue toward intentional relationship-building.
I met Tim at a recent conference and learned of his new book. I was in the dating game in the last millennium, and a lot has changed.
Today, we'll explore the art and science of questioning in dating—how the right questions at the right time can reveal compatibility, build intimacy, and ultimately lead to more fulfilling relationships.
In this episode, Tim shares how he developed his strategic dating framework by applying research principles to dating, emphasizing the importance of asking better questions about ourselves and potential partners. He explores how traditional metrics like "feeling a spark" can be misleading compared to questions about safety, visibility, and energy levels after being with someone. The conversation highlights how self-awareness, intentional action, and thoughtful questioning can increase the probability of building fulfilling relationships while also creating space for continued growth and evolution within partnerships.
Episode Notes
[00:00]The Misleading Spark in Dating
[00:47] Introduction to Curated Questions
[01:35] Meet Tim Molnar: The Dating Strategist
[02:21] The Power of Asking Better Questions
[06:06] The Analytical Approach to Dating
[08:34] Reverse Engineering Love
[13:35] Picking A Date Number
[15:40] Self-Awareness in Dating
[18:12] Emotional Rewards and Protections
[22:58] A Predictor of Long-Term Happiness
[30:30] Healthy Relationships and Happiness
[32:11] The Role of Dating Apps
[35:48] Evaluating Potential Partners
[38:03] Designing a Dating Process
[39:25] Proactive Dating Strategies
[40:32] Creating Rigid Implementation Intentions
[41:40] Building Confidence Through Tracking Progress
[43:05] The Role of Accountability in Taking Action
[45:09] Handling Disappointment and Rejection in Dating
[46:48] Understanding Ghosting and Its Implications
[47:51] The Impact of Digital Communication on Empathy
[48:53] Questions to Ask When Facing Rejection
[53:28] The Role of AI in Modern Dating
[54:17] Ineffective Questions in the Dating World
[01:00:25] Probing Questions to Reveal Deal Breakers
[01:02:37] Navigating Long-Term Relationship Changes
[01:03:49] Creating Space for Relationship Growth
[01:05:55] Balancing Self-Development and Dating
[01:11:32] The Importance of Growth Mindset in Relationships
[01:13:23] Hunting Field Mice or Antelope
[01:20:42] Final Thoughts and Encouragement
[01:23:07] Final Thoughts
Resources Mentioned
Date Smarter: A Strategic Guide for Navigating Modern Romance by Tim Molnar
Harvard Study of Adult Development
Questions Asked
When did you first understand the power of questions?
Would you like a cookie?
Can we please have a cookie today?
Why the switch going from all things lawyer like over to this new world?
Can you just give some background on what that looked like?
How does that academic background influence your questions about dating?
How might someone without research training develop similar analytical skills?
How can I meet someone who's gonna be a great life partner for myself?
What does my perfect day look like five years from now?
What was I eating for breakfast?
Where did I wake up?
Who did I wake up next to?
What type of books was I reading?
What was my physical health like, my emotional health, my social health?
Was I traveling?
Was I active?
What was I doing for work?
What did my finances look like?
Is there a way to reverse engineer that?
Has there been research done on this?
Would you be interested in going on a date with me?
Can I have a light for my cigarette?
Can I have directions?
Would you like to go grab a coffee, go for a walk, or grab some dinner?
What are those dating roadblocks?
Have I been getting outside of the house?
How does self-awareness inform one's approach to dating?
What do you really want out of this?
What do I actually need to get over just this next hurdle?
What are the lowest-friction actions that we can take?
What are some questions you work through with clients to help understand that?
What emotional rewards, maybe even protections, did you learn to seek in your earliest relationships?
How did I try to seek emotional reward?
Was it every time I cleaned up my room?
What kind of emotional protections did you need to develop?
If you didn't do those, were there consequences?
How do those inform what you're searching for in your current dating life?
What am I trying to optimize for?
Are there certain things that I've been trying to optimize for that are actually standing in the way of a healthy relationship?
Was that healthy?
What worked about it?
What was right and loving and just, and then what perhaps may be a little off?
How do you think about balancing that out, the feelings versus other metrics,
Was there a spark here?
Is there chemistry?
How am I feeling in my body at the end of this date or during this date? Do I feel safe? Do I feel seen? Am I energized?
Is this someone that I can make hard decisions with?
When one of my parents, who's dealing with dementia, needs to make some difficult decisions around end-of-life care, is this someone I can do that with in a productive fashion?
How does that connect with the analytical piece?
Does this person make me feel like I'm on a rollercoaster?
Is this person six feet?
Does this person make a hundred thousand dollars?
What types of questions can we be asking ourselves to suss these out earlier in the process?
How important this is to you?
When would we have met one another?
How do you get a hundred thousand swipes?
How does this person treat someone who they have nothing to gain or who they gain from?
How is this person going to show up in three months or three years when things get difficult?
How do I find my person?
How do I design a dating process that reflects my values, protects my energy, and increases my odds?
How do you proactively move that work outside of the home to some third space?
How can you be the catalyst and the change maker to really galvanize that change?
What is the behavior, when am I going to do this, and here is it going to happen?
How can I improve my chances of taking action towards those steps that I've identified as being helpful for getting me to where I want to go?
How do we encourage ourselves to get up at six in the morning and keep with our Monday, Wednesday, Friday gym schedule?
How should they think about going forward?
How do you work through that?
What's a good way to navigate that moment?
Can you tell grandma I'm not coming?
What kind of questions can we ask ourselves to remind us that what is playing out is very often not about us?
What could be going on here?
How do I say this in a way that's tactful yet honest?
What ineffective questions continue to be asked in the dating world?
What religion are you?
Do you do drugs?
Are you addicted to meth, or do the occasional edible while you're out on a camping trip?
What does that look like for you?
What are your definitions?
What are your traditions?
Was this date at least a six out of 10?
Am I willing to do this again?
What role does surprise play in the dating relationship?
What did you have here?
What deeper probing questions might reveal these potential deal breakers earlier on?
How can we investigate that?
Is this someone who could be a good partner?
Is that really what you're trying to optimize for, or can you ask thoughtful questions to determine your true values?
What am I really wanting?
How should one think about the longer term?
Are there things that we should think about in these earlier days that might help us in later years?
What kinds of questions can we ask on a day-to-day basis, or even week-to-week, month-to-month basis, to have that check-in that doesn't require three or five days?
What's been on your mind lately that we haven't talked about?
Not how much growth do you need to do before you're going to be ready to date, but who is the person that's going to help you grow, and who you're going to be able to help grow?
Have you checked out where the local courts are?
Are they looking for you to never change?
Are you gonna be able to embrace change for your partner, is your partner gonna embrace it for you, and what does that look like?
What does it look like to have some of those conversations?
What questions do you personally carry and revisit?
Am I hunting field mice or am I hunting antelope?
Am I spinning my wheels doing things that give me that false feeling of productivity, but aren't likely to hit in a bigger way?
Are you listening to anything good?
Do you want me to go on ahead, or do you wanna go ahead, or do you wanna keep chatting
Do you have any other thoughts or encouragement about questions that we haven't touched on yet?
Where's the best place for folks to track you down and see what you're excited about and understand all that you've got going on?