We’ve all heard the advice: Be vulnerable. Open up. Share more of yourself.
Sounds great in theory, but what does that even mean? You can sit across from your date and start spilling your deepest fears and biggest dreams, or share about that time you were two and threw a tantrum in a grocery store because they ran out of your favorite ice cream. (For the record, understandable.)
But will that actually create a connection? Not necessarily.
I hear this from clients all the time:
“I really put myself out there. I shared so much, but somehow, it still felt like something was missing.”
Or,
“I thought we had a deep conversation—I thought I opened up, but then I got feedback that they didn’t feel a connection, and I don’t get why.”
And my response is always the same:
“Did you just tell them the basics or did you share your feelings and the impact it has on you?”
Very often, daters will genuinely believe they are being vulnerable and opening up, but they are doing it all wrong.
Real sharing, when done right, doesn’t just help the listener get to know you. It creates a bond between both of you. When you share in a way that lets someone step into your world and feel what you feel, it draws you closer to each other. That’s the difference between simply telling someone something and truly connecting with them.
Sharing is important—it’s how we build trust and form real relationships. But there’s a right way to do it. It’s not just about listing off your life’s challenges like a verbal résumé of struggles. It’s about sharing in a way that brings someone into your experience, making them feel what you felt, and showing them who you are—not just what happened to you.
So how do you do that? The secret is in the how. It’s not just about what you share but how you share it. Are you giving just the facts, or are you sharing the story behind them? Are you letting someone see how an experience shaped you, changed you or still affects you today?
When you do this right, it’s no longer just about you sharing—it becomes something that connects both of you in a way that facts alone never could.
Here are some examples to show how to move from just telling to connecting.
When Life Took an Unexpected Turn
Fact-Only:
“My parents got divorced when I was ten.”
Sharing with Meaning:
“When my parents got divorced when I was ten, I didn’t really understand what was happening—I just knew my world felt like it had split in half. Once a week and every other Friday, I packed a bag to switch houses, and for years, I felt like I never fully belonged in one place. But looking back, I think it made me more adaptable, and it also made me really conscious about communication in relationships. I don’t take things for granted, and I know that love takes effort.”
Why this works: Instead of just stating a fact, you’re bringing your date into the emotional impact of the experience. You’re showing what it meant to you and how it still influences you today.
A Personal Challenge
Fact-Only:
“I take medication for anxiety.”
Sharing with Meaning:
“I take medication for anxiety, and honestly, it took me a long time to accept that I needed it. At first, I felt like it meant something was wrong with me, like I should be able to just push through on my own. But once I got past that, I realized it’s no different from taking medicine for any other condition. It’s actually made me more aware of my mental health and how important it is to take care of myself. And you know what? Life feels so much better now.”
Why this works: Instead of just stating the fact, this version shares the internal journey—struggles, realizations, and growth—which is what builds connection.
A Life-Changing Moment
Fact-Only:
“My grandmother passed away last year.”
Sharing with Meaning:
“My grandmother passed away last year, and it hit me harder than I expected. She was the person who always believed in me, no matter what. I still remember sitting on her porch as a teenager, venting about my life, and she’d just nod and say, ‘It’ll all make sense one day.’ And the crazy thing is… she was right. Losing her made me appreciate the people in my life more, and I try to carry her kindness with me every day.”
Why this works: Instead of just stating a loss, you’re sharing what this person meant to you and how their presence (and absence) shaped you. That’s what creates connection.
Career Choices & Pressure
Fact-Only:
“I don’t really like my job.”
Sharing with Meaning:
“I work in accounting, but if I’m being honest, it’s not my dream job. My parents really pushed me into it because it’s stable and practical, and I get why—they just wanted me to have a secure future. But lately, I’ve been thinking a lot about what I actually want to do. I’m not making any crazy moves yet, but I’ve been exploring other interests, and it’s exciting to finally give myself permission to think beyond just ‘what makes sense.’”
Why this works: Instead of just complaining about a job, this version gives insight into family dynamics, personal struggles, and a current journey of self-discovery—making it much more engaging and relatable.
Overcoming Shyness
Fact-Only:
“I used to be really shy.”
Sharing with Meaning:
“I used to be the kid who practiced what I would say before answering the phone. If someone called and I wasn’t expecting it? Straight to voicemail. I still have a little of that in me, but over the years, I’ve pushed myself to step out of my comfort zone—because I realized I don’t want to be the person watching life from the sidelines. And honestly? I’m proud of that growth.”
Why this works: It’s relatable and shows transformation. Instead of just stating you were shy, you’re giving a mini-story that paints a picture of what that looked like and how you overcame it.
These are a few examples. Use this idea when you are sharing vulnerable, important or deep parts of yourself. This does not mean you have to turn each conversation into a therapy session or talk about feelings when talking about what you had for dinner last night.
When to Share Deeper Things
Opening up is not just about what you share and how you share but also about timing. Some things are great to share early on, while others are better for later in the relationship. If a moment presents itself where sharing would make the conversation more meaningful, trust your gut and go for it.
That being said, timing isn’t just about how many dates in you are. It’s also about when and how you bring something up. You don’t want to share something deeply personal right at the beginning of a date—when the mood is still light, and you’re making small talk about your day.
You also don’t want to drop something vulnerable at the very end of the date, when she is about to get out of the car.
And definitely avoid bringing up something important when:
- The restaurant has gotten really loud, and your deep emotional moment is being drowned out by the guy at the next table explaining crypto.
- Your date looks tired, distracted, or just had a bad day—they might not be in the right headspace to fully hear and absorb what you’re saying.
- They’re hungry (this is a public service announcement: nobody is emotionally available before food).
The goal is to share when the moment feels natural—when there’s space in the conversation, when your date is engaged and present, and when it doesn’t feel forced or rushed.
Because sharing vulnerably is powerful, but only when the other person is truly able to listen.
The Right Person Will Appreciate the Real You
Sharing personal things can feel scary, but the right person won’t see your experiences as baggage—they’ll see them as part of what makes you you. And if they don’t? That’s valuable information, too.
At the end of the day, real connection doesn’t come from exchanging fun facts about our lives. It comes from sharing the experiences, emotions, and lessons that shape us.
So don’t just share the headline of your story—let them into the behind the scenes.
