How to debug boring dates | Ep 77
3 questions to ask yourself to rekindle the fire
Hi! I’m Joyce Zhang, Dating Coach for Tech Founders. I’ve been sharing weekly dating guides every Thursday since 2024. Some of my 2,500+ readers have credited it with helping them find love. Subscribe to get the next one.
When I was single, I went on ~80 dates/year. For a while, many were boring.
Like the overachiever I was, I thought, I just need to work harder: be more interesting, ask better questions, pick wackier date spots. But the conversation kept staying in what I now call “facts exchange”: where we’re from, what we do for work, what are hobbies are. I was already doing this cerebral exchange all day at work. No wonder I was bored.
Then, in 2023, I did my first T-group. I sat in a circle of 14 people for 30 hours over a weekend. There was no prompt. We were just to figure out how to connect with each other.
I’d taken time off a busy work period to go, and I’d come in with a deep sleep deficit. The first day was boring and exhausting. The conversation stayed heady, people were giving each other advice, and we were analyzing the premise of this group. I was falling asleep.
The second day, with the nudge of our facilitators, people started expressing their feelings. “I feel down about my dating life.” “I feel annoyed that we’ve made no progress in this group.” “I feel heartbroken hearing your story about your dad.” Whenever someone shared a strong emotion or, better yet, how they were feeling about me, I snapped awake.
After the experience, I realized I rarely talked about my feelings on dates. No wonder my dates were boring. I was so used to connecting intellectually (head to head) that I’d neglected what actually creates engagement: connecting emotionally (heart to heart).
How to debug boring dates
Go through these in order:
1. Are you genuinely curious about your date?
Beyond how attractive they are or how thoroughly they check your boxes, how interested are you in taking the time to discover this person as a human?
Many daters have lamented to me about dates they went on because they thought they “should” be going on more dates or because they didn’t feel confident shooting their shot with someone they were more excited about.
Your dates deserve your full attention, even if it means going on fewer dates to preserve your energy. Do what you need to take care of yourself so you can show up present and with curiosity.
2. What do you talk about on dates?
Many daters tell me they were excited to meet their date, but the conversation fell flat.
I ask them what they talked about. It’s usually some combo of work, friends, and travel.
I ask them to reflect on what they just told me. They usually say, “ok yeah that sounds pretty boring.” They were falling in the “facts exchange” trap I used to.
What about taking a small risk and getting a bit more personal? Why not ask them for the story behind why they chose each of their Hinge pictures? What about their first impression of you?
When we’re talking about each other, we’re far more engaged.
If you feel nervous to bring up the more personal topics, try naming that out loud. Which leads me to the next question…
3. Are you sharing your feelings on dates?
Even if you don’t want to talk about each other on the first date, you can still make topics as mundane as work far more interesting by sharing how you feel about it.
Example:
Sharing facts: “I’m working on this new GPU architecture project with my manager.”
I’m thinking, “Oh boy, I gotta start getting curious about GPU architecture. Here we go.”
Sharing feelings: “I’ve been so frustrated with my manager lately. I feel bashful about that because they’re genuinely so nice.”
Now, I’m invested. I have so many questions. What’s frustrating you about your manager? What does your manager do that’s nice? What makes you feel bashful? What will you do?
If you want to challenge yourself, try sharing how you feel about your date.
Example: “When you asked about my frustrating situation with my manager, I felt heard and understood.”
If you want to learn more about the framework behind this, I recommend checking out the 5 Levels of Communication from “Why your date didn’t feel a romantic connection.”
Try this
Before you commit to your next date, ask yourself: How genuinely curious am I about my date as a human?
During the date, pay attention to energy levels as you try different topics. What happens when you stay on work/friends/travel vs. what you think of each other?
For everything you share, try adding some color around how you feel about the situation. If you’re feeling bold, try sharing how you felt about something your date said or did.
What do you do to keep your dates interesting? I read every reply.
What should I break down next?
How to recover the conversational spark if you fall into “boring” topics (like work)
Deep dive on how to make work talk on dates engaging and connecting
More examples of how to share how you feel about your date
What to do if you keep picking people you’re not genuinely excited about
Love,
Joyce ❤️🔥
P.S. I’m hosting a workshop with Carole Robin, Ph.D. (Distinguished Stanford Teacher of Touchy Feely & Co-Founder of Leaders in Tech) at the AI Engineer World’s Fair on Monday, June 29 in SF. We’ll demo some of these connection skills live, then you’ll practice. Public conference passes are sold out, but you can request one here to attend the workshop.
P.P.S. If you want to debug why your dates aren’t leading to relationships and learn the skills to deepen connection with dates, I’d love to connect with you. Request a call for us to chat about coaching.
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Hi Joyce, I'd definitely be interested in your take on dating burnout.