Ten Reasons Why the Thought of Dating In Mid-Life Is So Scary

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The thought of dating after many, many years of being married was completely overwhelming to me. In the first few months after I was divorced, when friends were urging me to meet new people, I would get a pit in the bottom of my stomach. Honestly, I couldn’t even figure out what frightened me most.

But once I dissected the idea of dating into smaller pieces, I could put words to the things that terrified me. In talking with other singles who have decided to venture back into the dating world at mid-life, most of our fears are universal.

Here is a list of ten things that rattled me (and likely you too!):

  1. Wondering how I would ever meet anyone to date
  2. Trying to decide how to present myself – my story – to men
  3. Imagining a phone or text conversation with a prospective date
  4. Puzzling over what I would say when in person on a date
  5. Figuring out what to wear
  6. Thinking about how an actual date might go
  7. Questioning how I would handle rejection
  8. Not being sure what I brought to the table
  9. Not knowing what I wanted from dating
  10. Thinking about kissing, touching, and more!

Make your own list. Once we name our fears, we are one step ahead to conquering them.

Getting Through a Divorce To The Other Side

Let’s face it. Divorce is hard. Even if both parties agree, and the terms are amicable, the experience is completely unsettling. Everything that is familiar to you – your home, your mutual friends, your routine, your work, your traditions, your possessions, parenting – can and will likely shift radically during and after a divorce. That certainly happened to me.

During the last ten years of my 24-year marriage, I had plotted an exit strategy. In my head, in my heart, and in my gut, I knew I needed more stability, emotional support, less drama, and a fighting chance at happiness. But for many reasons, I waited to exit my marriage until my daughter started college. Take it from me: Planning a divorce in your head vs. initiating it — and then going through with it — are two completely different things. The former was fraught with silent stress and constant mental calculation. The latter rips off the band aid, catapulting those internal thoughts into an overwhelming flurry of details, decisions, paperwork, meetings, a gazillion tasks, and an unrelenting whirl of emotions.

With all that activity and emotion, who even has time to think about dating?!

How My Teenager Challenged Me to Consider Dating

The game changer for seeing that dating would be worth doing came from my smart, funny, sassy 18-year-old daughter who delivered dating observations in an inimitable teenage way:

“Mom, you don’t have a life. You gotta have some fun.”

“You need to find someone to love you before you get too old!”

And her zinger…

“Mom, you know what? You just need to get laid!!”

That last one did it for me. First, I was shocked! Then laughing at her impertinence, I decided if she could make light of my dating worries, so could I. She had just taken my carefully curated list of dating fears and scooted right to #10! What a jolt! It was time to consider how my future life could be excitingly different than the one I was suffocating in.

Dating Has Helped Me Feel Alive Again

Once I made the decision to date after my divorce, I needed a tool to help guide me. So, I created a list of dating to do’s. Every time I slide back into a fear mindset, I look at my list and move forward. I hope these ten “Date Like Kate” rules resonate with you.

  1. Be approachable.
  2. Have an attitude of respect and gratitude.
  3. Don’t prejudge a person before you know them.
  4. Take yourself less seriously.
  5. Embrace dating as an adventure.
  6. Don’t be afraid to reinvent yourself.
  7. Make authentic connections.
  8. Invest in genuine relationships.
  9. Approach dating with curiosity and hope.
  10. Don’t stay home – get out there!

May this new year lead you on a new life adventure. Write to me with all your dating questions at kate@katesomerset.com. I am here for you!


  • 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 www.KateSomerset.com.

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