Improve Your Dating Self-Confidence Right Now — Powerfully Small Tip #1

Confidence isn’t about what you have, it’s about what you believe.

May Pang
Hello, Love
Published in
6 min readOct 8, 2022


Image by Florin Radu from Pixabay

“I mean, it’s not like I’ve ever been a beauty queen or anything so with everything that happened this year, my confidence is at an all time low,” my client, Sheena, expressed to me.

Sheena has objectively had the worst year of her life. Her husband of fifteen years left her for someone else and the stress of coping with it led her to gain thirty pounds. To add insult to injury, the stress also resulted in seemingly endless bouts of cold sore outbreaks that were highly visible around her lip.

She was so distraught that she could not go to work and was eventually laid off. Now, living with her parents at the age of forty-five, she was feeling incredibly lonely but just could not see how anyone could find her attractive.

To work her way out of her despair, Sheena had tried all kinds of self-help and self-love books. But the part she continually struggled with was the self-affirmations.

“I’ve tried telling myself that I’m beautiful and sexy. My brain immediately reminds me that I had to buy larger clothes this week and my husband left me for someone older than me. After years of my internal critic telling me I’m unattractive, it’s just such a reach to say I’m beautiful that my brain immediately just tells me I’m lying.”

What Sheena was trying to do was the equivalent of someone who hadn’t worked out ever trying to convince themselves that they could win the Boston Marathon in 12 months.

What her brain needed was a smaller step that it could actually grasp on to and believe. Just like the average person would find it easier to believe that they could do a 5-mile run in a few months rather than win a marathon right away.

So, here is the first question I asked her to meditate on every day:

Question #1 — What is the next most believable thought you could reach for?

The aim of every self-help book is to help you love and accept yourself fully. That means all of yourself — flaws and all. For most of us, that’s a tall ask. Sheena felt like she was being asked to run a marathon when she had never even run a mile.

“Maybe you don’t feel beautiful but is there a part of you that you like?” I prompted.

Sheena seemed to really struggle with this, “I really don’t have any physical attributes that I’ve ever loved about myself.”

“What about things other people have mentioned?”

“When I was younger, people used to say I have pretty eyes. My niece still says that my eyes laugh when I do.”

“Is it possible that somebody could find your eyes attractive?” I asked.

“Well, it’s possible but not probable,” she laughed.

“I’ll take it! If possibility is all you can believe right now, that’s a good step.” I grinned back.

“You know, when I was younger, I had a nice waist. I just kinda let it go when I got married,” she reflected.

“Is it possible that you may one day regain a liking for your waist?” I prompted.

“Well, I have been excited about getting back in shape. But you know what I’m going to say…”

“It’s possible but not probable?” I guessed.

Sheena smiled and nodded.

“Ok, I want to not get stuck on the physical traits. What are some things that your friends and family appreciate about you?”

“Hmmmm….I mean, I get called over all the time when people are down. I think I can say I’m a good listener. Empathetic and non-judgmental,” she responded thoughtfully.

“Is it possible for you to believe that someone might be attracted to that?”

“Well, I would be attracted to a good listener who was empathetic! So, I guess…yes!” she smiled. “Okay. I can get behind that one trait.”

I encouraged Sheena to continue for another week by constantly reaching for the next most believable thought. This is how continuing that habit played out for Sheena and how you can do it too:

How you can apply this question to slowly build your confidence

When we started, Sheena had trouble believing she was beautiful, but her next most believable thought was that she had nice eyes.

She had trouble believing she was sexy, but her next most believable thought was that she could one day have a waist she liked again even if she had to work for it.

She had trouble believing she was an awesome catch but her next most believable thought was that she is a good listener and could be good company at least for one date.

The week after our session, Sheena went on a date. She told me that she spent extra time on her eye makeup and wore a dress that she thought accentuated her waist. She also made sure to be extra present and attentive to her date.

“I don’t think men ever notice makeup!” she laughed. “But I felt different inside. I practiced looking at my eyes in the mirror and smiling before the date and I held that image in my mind while I was on the date. I’m not sure how I feel about him, but we have a second date! He mentioned that I was easy to talk to and it felt like my intention to be a good listener had paid off.”

She also said that now that she was feeling slightly better about herself, it was easier to find more things she liked about herself. She remembered that she was an excellent cook and a very reliable friend. She began paying more attention to what people complimented her on and even started asking her family. Her friends and family reminded her that she was affectionate, had a wonderful laugh, an adventurous spirit, and a fascinating mind.

Each time she went on a date, she would find ways to highlight these traits or at least hold them in her mind’s eye. Six months later, she started dating someone she is now in a serious relationship with. Sheena may have a long way to go before fully believing that she is beautiful, sexy, and an awesome catch but her self-confidence has definitely improved. More importantly, she has a simple process to keep building her confidence.


If you struggle to find even one trait, remember that the first step is the hardest and it’s normal not to be able to find one right away. Then, follow these steps:

  • Remember things you may have liked about yourself in the past when you were feeling better or that others have frequently complimented you on throughout your life.
  • Try to expand beyond physical traits to things like kindness, good communication, patience, and empathy. These are things that will draw others to you more than you know. Read this article and this article for inspiration.
  • If you feel brave enough, ask your close family, friends, and colleagues what they appreciate most about you.
  • Finally, intentionally highlight or emphasize these traits in all social interactions and not just on dates.

At the end of the day, Sheena’s eyes have not changed since we started our coaching sessions nor had her interpersonal skills. The only thing that had changed was her belief on the value of these traits. Once she could see that it was possible that she could have attractive traits, she began highlighting them and noticing them more. It turns out, all she needed was a smaller first step that her mind could grasp on to. Maybe that is true for you too.

“People are drawn to the person you think you are and who you think you are can be changed.”

This is part one of a series of questions on building self-confidence. If you want to make sure you don’t miss out on the other questions, subscribe to my mailing list. You will also get 5 questions to instantly create intimacy when you sign up and regular tips on how to connect more authentically.

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May Pang
Hello, Love

Combining Storytelling with Science. Communication & Connection Coach. Would love to hear from you!💗 💙 Based in Boulder, CO.