The Imposter Syndrome and Dating

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So, let’s say you have decided to take the big leap of getting back into the dating world after a pause of a few — or many — years. Pat yourself on the back! It takes social courage to say yes to showing up again, whether you are looking for a relationship or not.

But just as you are convincing yourself that you are ready to spread your wings and meet new people, nagging doubts crowd your thoughts. We often use the term “imposter syndrome” to define negative messages we tell ourselves about being a fraud in the workplace.

But guess what? Negative thought patterns that derail our professional confidence can also undermine our belief in ourselves in personal situations…like dating.

If you give weight to self-doubting messages in your head, you might convince yourself that:

  • I am unlucky in relationships.
  • I have failed in the past; I will fail again.
  • No one will be interested in me.
  • I won’t be able to live up to anyone’s expectations.
  • I don’t deserve happiness.

How We Come to Believe What We Think of Ourselves

What we hold true about who we are comes from two sources:

  • what we tell ourselves about our abilities and skills, and,
  • how we receive what others say, both to us and about

In other words, we form an opinion of ourselves — not only from holding up our own mirrors — but also from paying attention to and then filtering what we learn from outside sources.

The caveat: If we listen to uninformed or unreliable sources, we can easily mislead ourselves into thinking we aren’t good enough.

When we grow up with supportive families, friends, teachers and communities, we receive frequent guidance, feedback, and compliments. We grow through life experiences. With trial and error, we learn that no one is close to perfect, but that we each have many unique and wonderful qualities. We congratulate ourselves when we succeed, and forgive ourselves when we fail.

The caveat: If we come from dysfunction, we must work harder to find role good role models who will demonstrate what healthy self-awareness is.

When we are fortunate to have workplace settings where there is regular feedback and constructive encouragement, our competence and knowledge keeps pace with our self-growth. We learn the necessity of preparation, the investment in education and training, and the value of having a workplace mentor.

The caveat: If we have unsupportive bosses or colleagues who undermine us, we must identify other sources of rational and non-judgmental thinking.

When we cultivate positive social interactions and relationships, we learn how to make and keep connections, build long-lasting friendships, and be an effective partner. Not all of our social connections will last a lifetime. But each one is an important building block in teaching us how to get better at being us!

The caveat: Especially in new dating situations, we may not get feedback at all. Absent receiving any, we make the critical mistake of inferring opinion where none exists.

Three Ways Not to Be a Dating Imposter

  1. Never tell yourself it all comes down to luck. A passive approach to dating will not give you the latitude to connect with others on your terms. Meeting new people is about confidence, approachability, and being authentic. When you demonstrate those three attributes, you are at the very best starting place to build genuine connections.


  1. Be open in your communication. If you enjoy the company of the person you are dating, say so. If you don’t, you are under no obligation to continue seeing them. If you are asked to give feedback, feel free to offer it, kindly and thoughtfully.


  1. Go with your gut and respect yourself. You know you, and when you are insincere. Behave in whatever way is appropriate for your values, your approach to life, and your short and long-term goals.


You’ll never be an imposter  — dating or otherwise — if you know who you are, and always show that person to others. I want to hear how you display your own brand of social courage! Share your stories with me at


  • Kate Somerset

    Kate Somerset is an author pen name for the book “Mom…You Just Need to Get Laid: The Adventures of Dating After Divorce”. Following a divorce after 24 years of marriage, and thirty years of being deeply rooted in professional and volunteer roles in Texas, Kate took a chance on a new life in New York City. She immediately fell in love with Manhattan and the many opportunities it offers. Kate’s book about 15 true dating experiences in New York City is an honest, humorous, and inspirational look on how to give yourself and romance a second chance. One of the most universal struggles faced by all of us – building effective social connections – is the focus of Kate’s monthly column for The Three Tomatoes. Published by Brooklyn Writer’s Press, the book and Ebook are available on Amazon. An audiobook produced by The Three Tomatoes is on Amazon and Audible. Learn more about Kate at

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