What’s Your Most Embarrassing Dating Moment?

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Raise your hand! If, like me, you have re-entered the dating world in mid-life, I guarantee something embarrassing has happened to you.

From cringeworthy dating conversations, to making the wrong assumption about a man, to running into former (or current) dates at grossly inconvenient moments, we’ve all been there.

My experiences run the gamut!

Of the 15 true stories I describe in my dating book “Mom…You Just Need to Get Laid”, at least half feature a moment that went awry. Sometimes it was me, sometimes it was him, and sometimes it was a third party. No matter who perpetrated the embarrassment, I am happy to say I am still alive to talk about it!


As much as I want to crawl in a hole when I find myself center stage in an awkward dating moment, I keep moving through it. And as much as I think I’ll never recover, I always do.

Here are just a few examples of what has happened to me on dates, and what I did about it:

  1. Anthony was the first man I went out with after I decided to plunge head first into the dating pond after my divorce. He and I had a flirty, almost smoldering text exchange (after a four-hour intro call!), and I just knew our first meeting would be amazing. But not only was it not amazing, he called me a few days after the date to say he just hadn’t felt an emotional connection.

WHAT HAPPENED NEXT: Although I was surprised and disappointed, I rallied and asked him for an “exit interview”. He agreed, and I learned a lot about him and myself too!

  1. Levi and I were both dating other people while we were going out with each other. It wasn’t a problem until one Friday night after he had enjoyed my homemade dinner. As he was saying his goodbyes, we made the accidental discovery that the next evening we would both be attending the same Broadway show. It was obvious from his discomfort he had a date (I didn’t) and he begrudgingly told me where his seats in the theater were. I promised to find him and say hello. The next evening, Levi went out of his way to make sure his date didn’t meet me, even leading her in and out of the theater via the alley!

WHAT HAPPENED NEXT: The following morning, Levi sent me a text as if his avoiding me was perfectly normal. I called him on it; he apologized, admitting he hadn’t known what to do. We continued to date, and he subsequently quit seeing the other woman.

  1. Nick moved in two doors from me in my large New York City apartment building. We began spending time together as friends, but I was almost sure there was also a spark there. When one of my girlfriends visited me from Texas, she was convinced that he was interested in me. When she returned home, I sent her a text describing Nick’s latest friendly overture towards me. Only the text mistakenly went to him, not her!

WHAT HAPPENED NEXT: In five seconds, my brain registered what I had done, but it was too late. I couldn’t take it back. So, I did the only possible thing I could. I messaged Nick again, explaining that my friend thought she saw something between us, and that I was texting her to follow up on that conversation. My confession didn’t motivate Nick to upgrade our platonic relationship to a romantic one. But thankfully, since we lived down the hall from each other, it also didn’t ruin our friendship either.


Whether with dating or in life, being able to pull yourself up and out of embarrassing moments is a key survival skill. I hope you’ll read my book to discover how I have learned to work through so many unexpected moments in the dating world.

Here are my top three tips for you:

  1. Laugh about it. Nothing makes us more likeable than having a sense of humor. Remember that the other person may be just as uncomfortable as you are. So, take the lead in finding what’s funny, and you will convert what’s miserable to memorable!
  2. Tease yourself. One of my favorite expressions is: “Did I really just say that?” When I momentarily think of myself as the third party, I swap a sense of shame for an observant reality check. And showing you’re vulnerable always helps others relax too.
  3. Ask the other person to forgive you. Try saying: “Wow! I can’t believe I just made you witness that crazy moment. Forgive me!”. Apologizing (if the goof is ours) immediately disarms the other party and makes our behavior authentic.

I’d love to hear your stories of embarrassing dating experiences and how you have recovered. Please share them with me at kate@katesomerset.com. Onward and upward in getting through and moving forward!


  • 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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