To listen to my entire conversation with Allison Brenner, head to Apple Podcasts, Spotify, or YouTube.
There is something fundamentally frustrating about dating that we don’t talk about enough: there is almost no feedback.
You can go on a first date, think it went really well, come home excited, and then never hear from the person again.
Maybe they weren’t attracted to you. Maybe you talked about your ex too much. Maybe you came across as negative. Maybe you spent the entire date talking about work. Or maybe you did absolutely nothing wrong, and you simply weren’t their person.
The problem is, you usually never know.
And if you don’t know, how are you supposed to get better at dating?
This is one of the unique advantages of working with a matchmaker. After nearly a decade of matchmaking, I can tell you that the feedback we collect after dates is incredibly valuable. Sometimes it confirms that two people simply weren’t a match. But sometimes we start hearing the same thing over and over again.
And that’s when you have to pay attention.
If one person tells you that you talk about your ex too much on first dates, maybe it was a weird night.
If five people tell you that you talk about your ex too much on first dates, we have a pattern.
And patterns are where growth happens.
You May Be Self-Aware, But Are You Other-Aware?
On this week’s episode of Dating Rehab, I spoke with feedback expert Allison Brenner, whose background in psychotherapy and organizational psychology led her to create a system called InnerVue that allows people to receive anonymous feedback from the people in their lives.
One of the most interesting concepts Allison introduced during our conversation was the difference between self-awareness and “other awareness.”
We hear about self-awareness constantly.
Are you aware of your triggers? Your attachment style? Your strengths? Your weaknesses?
But there is another question that might matter even more when you’re dating:
Are you aware of how other people experience you?
Those are not always the same thing.
You might think you’re being confident. Your date might experience you as dismissive.
You might think you’re showing someone how accomplished you are. They might experience the conversation as you talking about yourself for two hours.
You might think you’re being discerning. They might experience you as judgmental.
You might think you’re being funny and sarcastic. They might leave wondering if you actually liked them.
Your intention matters, but so does your impact.
And sometimes we have absolutely no idea what that impact is.
Dating Apps Have Made This Even Harder
One of the problems with modern dating is that it has become incredibly easy to disappear.
You don’t have to tell someone why you don’t want a second date. You can unmatch them. Stop responding. Send a polite “I didn’t feel a romantic connection” text that tells them essentially nothing.
And then you move on to the next person.
There is very little incentive to have an uncomfortable conversation with someone you met once.
I understand why. I’m not suggesting everyone needs to send a detailed performance review after a Hinge date.
But the downside is that people can date for years without realizing they are doing something that is getting in their own way.
This is where trusted friends, coaches, matchmakers, and even former partners can be incredibly valuable, assuming you’re actually willing to hear what they have to say.
Anonymous Feedback Can Tell You What Your Friends Won’t
One of the reasons I found Allison’s approach so interesting is that the feedback can be anonymous.
Because as much as we say we want honesty, honesty has consequences.
Your best friend may have noticed that you become incredibly negative whenever you talk about dating, but she doesn’t want to hurt your feelings.
Your sibling may think your expectations are unrealistic but doesn’t want to start an argument.
Someone you dated may know exactly why the relationship didn’t progress but doesn’t want to deal with your reaction if they tell you.
Anonymity can remove some of that fear.
And again, I’m much less interested in one person’s opinion than I am in patterns.
One person’s feedback can be subjective.
When several unrelated people are telling you the same thing, that’s information.
You don’t have to agree with every piece of feedback you receive. But you should probably be curious about it.
The Other Side of This: How Do You Give Feedback Without Hurting Someone?
Receiving feedback is only half of the equation.
We also need to learn how to give it.
One thing Allison said during our conversation really stuck with me. Before giving someone difficult feedback, make your intention clear.
Something as simple as:
“I have something I want to share with you, and I want you to know I’m saying it with love and kindness.”
That changes the entire tone of the conversation.
Feedback shouldn’t be an attack.
It shouldn’t be, Here are all the things you’re doing wrong.
It should come from a place of, I care about you and I think knowing this could help you.
I’ve experienced this in my own work. I’ve had a client bring something up to me that could easily have made me defensive. But because he approached me gently and communicated what was bothering him clearly, I could actually hear him.
We addressed it. We solved it. And then we moved on.
That’s what healthy communication looks like.
Stop Letting Things Fester
This applies far beyond first dates.
In relationships, people often avoid giving feedback because they’re trying to “keep the peace.”
But avoiding an uncomfortable conversation doesn’t actually create peace.
It creates resentment.
Something small bothers you. You don’t say anything. It happens again. You still don’t say anything. Six months later, you’re furious about something your partner didn’t even realize was an issue.
Healthy relationships require two people who can say:
This bothered me.
This hurt my feelings.
I need something different from you.
And then, just as importantly, they require someone on the other side who can hear those words without immediately becoming defensive.
That doesn’t mean you have to agree with everything your partner says.
It means you’re willing to understand their experience.
If You Keep Getting the Same Result, Get Curious
If you’ve been dating for years and every relationship seems to end in the same place, it might be worth asking yourself a difficult question:
What am I not seeing?
Not, What’s wrong with me?
Not, Why doesn’t anyone want me?
But:
Is there a pattern here that I haven’t been able to recognize on my own?
Ask people you trust.
Ask the friend who will actually tell you the truth.
Think about the feedback you’ve received from past partners instead of immediately dismissing it because the relationship ended.
And if multiple people are telling you the same thing, resist the urge to explain it away.
Feedback isn’t a verdict on who you are.
It’s information.
And sometimes that one piece of information is exactly what you need to stop repeating the same dating experience and finally create a different one.
Listen to my full conversation with Allison Brenner on this week’s episode of Dating Rehab, where we go deeper into how to give feedback, receive it without becoming defensive, and use it to build stronger relationships.

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