Dating Advice from My Mother

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As a teenager, I was a slow starter in the dating department. I wasn’t one of the popular girls in my high school. An “in crowd” of my classmates were magnets for the attention of teenage boys. These girls always looked fantastic, seemed to know what to say and how to flirt, and were constantly in demand.

I was intimidated by the popular boys.  My dates were with guys who were quieter, more academic, and less experienced at dating. The “it” girls wouldn’t have been caught dead with any of them.

But I carried on. And a surprising thing happened. With each date I had, I gained more confidence. Even though I was a teenager and sometimes ignored my mother’s advice, when she talked about dating, I listened. Her wisdom took me places I wouldn’t have found on my own.

“Have courage and believe in the process, Kate,” she said. “You never know what will happen until you try. So go!” (Did your mother tell you the same thing?!)

Now What? Lessons Learned About Dating in Midlife

Now decades later, and after a marriage of almost 25 years, I found myself single and hearing my mother’s words all over again. And guess what? Her advice (mostly) still applied. Having courage and showing up has been 9/10 of the battle.

Now that I am letting myself be seen, here’s what I have learned about dating after divorce:

  • Going out with LOTS of people has built my self-esteem. (Check, Mom!) When I was first divorced, I wasn’t even sure I wanted to date. But the more I thought about it, the more it appealed to me. I liked the idea of meeting all kinds of people. Even more, I relished the chance to show up in the world as a whole new version of myself. And it I feel better about myself as a single person than I did in a marriage where I was lonely and discouraged. 
  • I get to choose who I want to see with no obligation. (Sorry, Mom! At this age, I give myself permission to say no thanks if I am not feeling it.) When you decide to date again after many years of marriage or singlehood, you have complete and total decision-making power. You pick the type of person(s) you want to spend time with, and say no to those who don’t appeal to you. The advantage you have over being a teenager is in having lived a big chunk of life and gaining wisdom along the way. You know who you are. And you not only know what you want; you know what you don’t want!

In my book Mom, You Just Need to Get Laid: The Adventures of Dating After Divorce, I share 15 true dating stories about 15 vastly different types of men. Extroverts/ introverts, intense/laid-back, younger/older, always in charge/risk-taking, and serious/happy go lucky. Dating so many different types of men has taught me how varied we all are. And that has helped clarify who I find most interesting and appealing. I like having choices, and dating many people has provided me those options.

  • Teenagers and mid-life daters equally experience feelings of nervousness, anxiety, and excitement. Before every date I go on, I still get butterflies in my stomach…just like in my teens. (My mother reassured me that was teenage normal.) I think about what to wear and what I’ll share. I imagine how the date will go. And I get excited about the new experiences I will have, even if they aren’t all as planned!  
  • It takes courage to show up. It takes courage to let ourselves be seen. It takes courage to be vulnerable. (My mother and Brene Brown agree!) There is nothing easy about getting ourselves ready to meet someone new. I psych myself up for it – each and every time. But I am never sorry I take the plunge. More times than not, I come away from a date grateful to have made a new connection.

 How Do You Show Up?

Choosing to date in mid-life is your call. The timing has to be right and you have to be ready. If you decide to date, make the decision enthusiastically. Believe in the wisdom of your decision. And show up with courage and confidence.

Both in dating and in life, the decisions we make provide us the opportunities we have.

If you give it a go, that choice could lead you to a new relationship. If you say no, the option of having that new relationship will not exist.

Think about it. And let me know what you decide. I am interested! Write me at Let yourself be seen!


  • 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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