Six mistakes women make in dating

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When single women compare stories about dating, inevitably the talk turns to how challenging the dating scene is. Certainly the pandemic hasn’t made meeting prospective suitors any easier. But before we throw up our hands in dismay, let’s take a look at our dating readiness.

What makes us prepared to begin mid-life dating for the first time – if never married, newly divorced or widowed – or to re-enter the dating world if we stepped away for a period of months or years? Is there a scorecard to help gauge how we could do best in the dating world?

First things first.

Decide how you define success in dating.

Is it meeting new people?

Having fun?

Enjoying new experiences?

Making friends?

Finding someone to be in a relationship with?

Depending on your answer(s), you’ll have a better roadmap to begin your dating journey.

When I first moved to New York as a long married and then newly single woman, my dating goal was not to get into a relationship. Instead, I wanted to build community for myself. That meant meeting as many people as possible, and yes, going on lots of dates.

It had been more than thirty years, and to say I was rusty was an understatement! So I needed to learn a lot about what to do and what not to do.  I hope these pointers from my experiences will be helpful to you.

Here are six common mistakes I believe women often make in mid-life dating:

1) Not believing you have anything to offer — I am amazed at the talented, accomplished women who have somehow convinced themselves that what makes them good in their professional roles won’t translate to their personal lives. I am here to tell you that men continually say that they are attracted to smart, independent women who are passionate about something, anything! Never forget that the creative, organizational, and communication skills you develop in the workplace matter outside the workplace. Take that to heart.

2) Judging before getting to know the individual – sometimes we lump people together by stereotypes and then don’t take the time to get to know them individually. If you label people by categories – the man who doesn’t have children, the man who works a lot, the man who has never been married, the man who is younger than you, the man who lives too far away, etc., you’ll first have to get past your preconceived notion before you get to know the person. I am not saying you shouldn’t have standards, but relax your strict approach to pedigree and type, and you just might meet an amazing person.

3) Not giving a date a second chance – okay, it’s true that we sometimes immediately know a second date is not of interest. But when you aren’t sure, give it a go one more time. You might be surprised to discover that the more you get to know someone, the more appealing they are.

4) Accepting the invitation, but not putting in the effort – I always approach a date like I would a job interview, keeping in mind that the first impression is made in ten seconds or less. That means what I wear, how gracious I am in saying hello, and how communicative I am is how I show up. Those signals say to my date how much I am willing to invest in our time together.  It’s all about the energy we give off that reveals how much we care to be there.

5) Thinking of dating as drudgery – if you believe that dating will be filled with tribulation and challenge, then it likely will be. However, if on the other hand, you think of dating like going on a grand adventure, you will open yourself to the possibility that it will be enjoyable. Imagine that you plan a vacation and then dread it before you go. Your negative view would surely color your experience. Instead, if you are excited to make the trip, it’s likely you will find it far more satisfying.

6) Giving up too easily – everything we do successfully in life requires effort. Looking for work, caring for children, making and keeping friends, and building dating relationships takes time, intentionality, and perseverance. It’s easy to get discouraged about any and all of these pursuits. But we know from experience that our success comes from the energy we apply to it.

So don’t be hard on yourself. Celebrate the wins. Laugh at your funny stories. I have had so many I captured fifteen of the best ones for my book Mom…You Just Need to Get Laid: The Adventures of Dating After Divorce.

I would love to hear yours. Please write to me at And best wishes to you on your dating success!





  • 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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