dating success

It's relational self-awareness.

I looked over at my third date and thought, “Something is going terribly wrong.” Why wasn’t I having greater dating success?

But what?

Here was an attractive, successful man — an intellectual, who was talkative, and had a variety of interests. He was widely read, and his musical tastes were broad. His children were grown with flourishing careers.

Yet, as we took turns learning more about each other, I found myself feeling increasingly uncomfortable. My date debated and challenged the accuracy of my comments. I felt showed up as if this was a competition. He seemed to need to educate me. I wished he could have relaxed and shared himself with me.

I grew embarrassed by my seeming lack of knowledge. All of which, I found odd since I’d earned a doctorate in psychology, once had a thriving private practice, had traveled extensively, and now was growing a writing platform. I knew my knowledge was diverse, so what was going on?

The Importance of Relational Self-Awareness

Dating expert Dr. Alexandra Solomon points out that to achieve a happy and healthy dating relationship, we need to learn to use what she calls “relational self-awareness.”

She defines this as “paying attention to your patterns, pain points, strengths, and blind spots,” and says, “it’s the essential foundation of a healthy intimate relationship.” She advises those of us dating to “stay curious about why you do what you do, feel what you feel, and think the way you think” as you choose your future partner. This information is critical in selecting the right person to navigate the usual bumps of life we all experience.

According to Dr. Solomon, relational self-awareness is more important than attractiveness, having compatible hobbies, or coming from a similar cultural background. She says, “Real love starts with you. Understanding who you are and what you ‘bring to the table’ lays the foundation for loving someone else.”

What Effect Am I Having on My Date?

She suggests we begin this process by asking ourselves,

“What effect is the way I am presenting myself having on my date?”

So, thinking back to that evening, I believe I stayed engaged. I think I exuded warmth and respect throughout our time together. I used eye contact and smiling to show interest. I listened as he talked and asked follow-up questions.

But was I successful?

Since this was an arranged date, I texted my matchmaker and asked if the post-date feedback indicated I came across warm and friendly. Her response was, “Absolutely!”

Great! Okay, so my intentional dating behavior gave off the vibes I’d wanted.

Did my date ask himself this same question?

Most of us don’t seem to know the importance of doing this. It’s easier to focus on what we are looking for in our desired match rather than how we make this person feel.

This man didn’t seem to pay attention to how I might experience being challenged on several of my answers. Plus, he looked down at his plate several times in such a way I suddenly felt alone in the room. Like he’d disappeared. I’m doubtful he was aware of the effect he was having on me.

How Does It Feel To Be With This Person?

Dr. Solomon then encourages us to ask ourselves:

“How do I feel in this person’s presence?”

This question is the reverse of the previous one. We shift the focus from how we are presenting ourselves to how our date is making us feel about ourselves.

Being with our date should make it feel good to be in our own bodies. We should feel free to be open, which increases our connection to the other person.

Yes, it’s true that each of us brings our history of past experiences, emotional baggage, and our unique take on the world. But, it’s important to ask ourselves:

  • Do I feel free to be me when I am with this person?
  • Does he or she create an environment that’s inviting and accepting?

Throughout the date, I remained tense. I was beginning to feel oddly less than my partner. It was as if I wasn’t enough and had to work hard to be more. The right person should make it easy for me to be me.

What Do I Want from This Relationship?

Dr. Solomon suggests we next ask ourselves:

“What do I desire?”

Everyone wonders if our date likes us. It’s natural to be preoccupied with thoughts of does he or she think I’m attractive? But, we mustn’t overlook these essential questions:

  • How do I feel about this other person?
  • Can I see myself hanging out with this individual?
  • And, can I imagine having a long-term relationship with him or her?

The first date isn’t too soon to ask these questions. They will give guidance on whether it’s worthwhile to schedule a second date or if it’s better to move on.

Throughout our time together, it was clear this guy liked me. Midway, he asked me for my number and suggested we have a follow-up date. Interestingly, I don’t think he realized I didn’t feel the same. I wished I had had the courage to have been bolder about how I was feeling. Maybe we could have talked about it.

As I drove home, I realized this type of relationship was nowhere near what I wanted. I couldn’t imagine the stress of having to fight for every opinion. Of not feeling safe enough to be me.

I felt ashamed, though, that I hadn’t been more open about my side of the experience. Maybe my date wouldn’t have listened, but maybe he would have. I didn’t give him a chance and missed the opportunity of greater insight for both of us.

The Importance of Checking-in

Thinking through Dr. Solomon’s advice, the outcome of any given date success needs to more than asking ourselves if he or she is cute enough or has the right career. It needs to be about us.

We need to check-in with ourselves. To ask ourselves hard questions.

We need to be curious about the impact we are having on our date. What kind of vibes are we sending? Are we acting threatened or defensive? If so, why? How would we like to be perceived? And, what can we do to make that happen?

Then we need to ask ourselves how is this date making us feel? Do I like who I am when I’m with this person? Does he or she bring out the best in me? Can I imagine a future with this person?

Jodi Picoult, in her book, My Sister’s Keeper, says it best about love: “You don’t love someone because they’re perfect, you love them in spite of the fact that they’re not.”

I’m learning that finding this kind of love isn’t about swiping left enough until I find the “just-the-right” look. It’s ironically best achieved when I slow down, tune into myself, and become more relationally self-aware.

Interested in learning who I’m using for Matchmaking Services?

Check out Tawkify!


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3 thoughts on “A Better Tool To Achieve Greater Dating Success”

  1. I’m pretty sure that I could fall in love with you, but I’m in Jacksonville, Florida which is a little too far from where you are…..for a cup of coffee and conversation.

    I live in a single-family house with a large jealous standard poodle. Do you tolerate animals? That says a lot about people.

    You need someone who will make sure that you are not ever hurt again. How can I “watch your back” from here?

    I love listening to your writing.


    • Oh, Chuck–you are the sweetest. Thank you!

      I hope you will watch for my latest post I’m putting up in a few minutes about the complexity of dating in my 50s. I’m glad you like listening to me read it. That’s a new experiment. I’ve been curious about how it is going over. Your feedback is very valuable.

      Yes, I hope to find a love who has my back and protects my heart <3.

      A jealous poodle, huh? I used to a Goldendoodle who felt the same way. I sure miss her.

      If you find yourself in the Austin area, let's have that cup of coffee.

      All the best,


  2. Kerry,

    As a 36-y/o male who has struggled to have a successful relationship, this article has been wildly helpful to help understand how asking “what” instead of “why” and checking in with yourself through the lens of your partner is so important. Thank you for sharing!


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