“Be Yourself” Doesn’t Work: Personalized Dating Strategies

1
Mar

Joanna brushed a strand of hair from her face as she surveyed the restaurant. She hadn’t expected to be dating at this stage of life, but here she was.

Catching sight of Michael by the bar, she straightened her shoulders—the same adjustment she made before client meetings. They exchanged smiles, and something about his warm eyes eased the tension she’d been carrying all day.

Conversation flowed naturally. Michael had an unpretentious charm and asked thoughtful questions. When her phone buzzed, she hesitated before silencing it.

“Important?” he asked.

“Just work,” she said, but found herself explaining anyway. “I’m leading our department’s restructuring initiative.”

Michael nodded appreciatively, but his gaze flickered briefly toward the bar.  

As dinner progressed, they touched on various topics—films, travel, neighborhood changes. Yet Joanna found herself most animated when discussing her team’s recent success.

When Michael mentioned his passion for sailing, Joanna smiled and asked a question, then found herself drawing parallels to organizational teamwork before she even realized it.

After dinner, they walked together to the parking lot. The evening air held the first hint of spring.

“This was nice,” Michael said, his smile genuine but somehow conclusive.

Driving home, she replayed the evening. Had she been too focused on work?

She was herself—engaged, interested, present. Yet something had remained just out of reach.

The Problem with “Be Yourself”

“Be yourself.” This is the dating advice most women over 40 have heard repeatedly. It sounds simple and freeing. But for many women, it simply doesn’t work.

This advice suggests that nothing else is needed – no skills to learn, no adjustments to make. It wrongly assumes you already know how to create connection and chemistry in romantic relationships.

Sometimes “being yourself” is exactly why you don’t get second dates. This advice ignores that the way you connect in one area of life doesn’t automatically work in another. Dating is different from work, friendships, or even past relationships—it requires skills and awareness that aren’t always instinctive.

What Joanna’s Date Shows Us

Like many women, Joanna thought being herself was enough for finding Mr. Right. She was being herself on her date with Michael, but this approach didn’t lead to a connection. By staying in familiar territory, Joanna inadvertently shaped the evening around her world instead of creating shared space.

Without thinking, Joanna changed the subject from Michael’s love of sailing to teamwork at work. By doing this, she missed getting to know Michael better, and he didn’t learn much about her beyond how much she loved her work.

Understanding Dating Blind Spots

Have you ever left a date feeling like you had a great conversation, yet something was missing? That’s often a dating blind spot—habits that feel natural but may quietly block deeper connection.

Dating blind spots can show up in many ways—talking more about your interests than asking about his, bringing up past relationship problems too early, or being so focused on making a good impression that you forget to evaluate if he’s right for you. These tendencies often take shape over decades, influencing relationships in ways you don’t always realize. Years of experience reinforce these patterns, making them feel natural—even when they work against you.

Repeating these same mistakes can quietly erode your relationship self-esteem. The issue isn’t about self-worth—it’s about recognizing what truly creates connection.

Recognizing blind spots can feel like seeing yourself in a new light—one that explains dynamics you never meant to repeat. It might mean facing feedback you’ve long brushed aside or realizing certain behaviors have led to the same painful endings.

Beyond Simplistic Advice

“Be yourself” ignores an important truth: dating requires specific skills that don’t come naturally to everyone. What works in your career or friendships often fails to create romantic connection.

The direct communication style that earns you respect at work can feel intimidating on a date. The problem-solving focus that moves your career forward can make dates feel like work projects, not fun.

Different situations naturally call for different approaches. You wouldn’t use the same communication style with your best friend as you would with your boss. Dating also requires its own approach – one that creates connection and chemistry rather than just interacting the same way you do in other areas of your life.

This isn’t about changing who you are. It’s about understanding how your habits and tendencies shape the energy between you and someone new. It’s like knowing which outfit fits which occasion—you’re not changing who you are, just choosing what best suits the setting.

Understanding your blind spots doesn’t instantly change ingrained habits. Awareness alone rarely transforms patterns. You might clearly see your tendency to talk about work yet still find yourself doing it on your next date. Real change comes through practice and sometimes discomfort. This isn’t failure – it’s part of growth. If you’re aware of your pattern, you can catch yourself early in the date and make a quick “flirt fix” – shifting back to more engaging conversation.

Successful daters know when they create closeness or distance. Moving beyond “be yourself” with this kind of self-awareness helps to create the chemistry and close relationships you’re truly looking for.

Next time you walk away from a date wondering why you didn’t click, ask yourself: “How did I engage with him tonight? Did it create the connection I wanted?” This simple check-in might reveal insights that open doors to more meaningful interactions.

Beyond “Be Yourself” in Dating

Many women over 40 wonder why being themselves isn’t creating the chemistry in relationships they want.

I help women identify what’s really happening in their dating interactions and develop approaches that spark meaningful chemistry with quality men who appreciate all of who they are.

If you’re ready to move past frustrating dates and create real chemistry, let’s talk. Contact me here for a complimentary consultation.

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Comments

  • Sandra says:

    I’ve been told that I needed to loose weight. Change my hair color. Go to clubs have a drink and dit st the bar is where guys notice you more. You’ll have to settle for second best since you are not good enough for the highest quality of men. You’re to stuck up is why you don’t have a good man in your life. My problem is I’ve got people who are up my butt sll the time to take care of and who do everything they can to make me look bad to the guy that I’m trying to start a relationship with. My mom has to hug and kiss everytime that she gets close to them which makes them feel uncomfortable and I try to talk to her about it but she tells the guy that I was mean to her about and then he starts backing away from me until she’s go him fully gone
    She says that she should meet them first before I start dating them to see if she likes their looks. I’ve had it with all the crap and I just want to get into a good relationship with the guy I’ve been talking to and stay away from all of my family. Got any advice for this mess?

  • Sandra says:

    I’ve been told that I needed to loose weight. Change my hair color. Go to clubs have a drink and dit st the bar is where guys notice you more. You’ll have to settle for second best since you are not good enough for the highest quality of men. You’re to stuck up is why you don’t have a good man in your life. My problem is I’ve got people who are up my butt sll the time to take care of and who do everything they can to make me look bad to the guy that I’m trying to start a relationship with. My mom has to hug and kiss everytime that she gets close to them which makes them feel uncomfortable and I try to talk to her about it but she tells the guy that I was mean to her about and then he starts backing away from me until she’s go him fully gone
    She says that she should meet them first before I start dating them to see if she likes their looks. I’ve had it with all the crap and I just want to get into a good relationship with the guy I’ve been talking to and stay away from all of my family. Got any advice for this mess?

    • Dr. Susan says:

      Hi Sandra,

      Nice to hear from you. It sounds like you are getting a lot of harmful advice.

      Don’t listen to these people who are so critical of you. They may not truly want you to find a good relationship.

      You don’t have to introduce these men to your family. It’s probably a good idea to wait to meet your family until he’s serious about you and you’ve met his family.

      Please let us know how it goes with you.

      Warmly,
      Dr. Susan

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