Life, Liberty and Tonia’s Pursuit of Happiness

Written by Paola K Amaras & Paul T. Kraly

Written by Paola K Amaras & Paul T. Kraly

The pursuit of happiness in today’s world most likely refers to love and romance. Overall we, as a society, enjoy the idea of being with someone else whom we can interact with, be intimate with, and share a life with. For some, it’s a lifelong struggle, while for others it’s a cake-walk. For Tonia DeCosimo, columnist for online dating giant Zoosk and author of her upcoming book Single and Not Settling: A Journey of Surviving the Dating World, it was somewhere in the middle. She spent a great deal of time searching for love, and in the interim dated some colorful, unique, and completely unforgettable characters.

Her new book is a memoir of adventures and misadventures in dating for the 21st century, a candid look at the do’s-and-dont’s of dating, mixed with humorous anecdotes and recollections sure to have the reader smiling — and, better still, more confident in finding true love.

We caught up to Tonia as she was sharing her new book cover with us, that of a single goldfish about to swim into a crowd of smaller fish. “It’s quite appropriate,” she laughed. “A lot of fish in the sea, and the single person is trying to sort through the waters and catch the right one.”
And that’s Tonia’s wit and wisdom shining through. We were able to sit down for an interview recently, and get her thoughts on dating, the pursuit of love, and of course her new book.

What made you write this book and what makes it unique from all the other dating books?

I woke up one morning when I was 23 expecting to spend the day shopping for an engagement ring with my long term boyfriend, who had proposed the night before. However, when I arrived at his apartment to pick him up, I overheard him on the phone making a date for that night with another girl. That’s how I began my dating life! For the next 20 years, I literally went on more than a hundred blind dates and first dates. I had highs and lows, laughs and tears. I met new men in just about every conceivable way: Internet dating, singles bars, speed dating, shares in summer houses with other singles. I had long term relationships and short term relationships. I was almost married a couple of times and ended one engagement three weeks before a planned large wedding.

I was getting dates, but I wasn’t getting the right dates. Yes, I met lots of nice guys, but none were right for me. And I also met more than a few not so nice guys — stalkers, liars, and general whackadoos. Through it all, the one thing I knew was that I didn’t want to settle and get married just so I could say I was married. When I turned 40, I realized I was a statistic, one of the millions of women who didn’t follow the traditional path set down by their mothers. I had a successful career, I owned my own home, and I had dozens of friends. But I was still single.

I wrote this book because I wanted to share my journey with other women. It’s a memoir of my own personal experiences through the dating world, but I think it will be helpful and speak to any woman who has ever searched through dozens of profiles on dating sites or cried herself to sleep because she realized that she had to end a relationship with a guy who drank too much, watched too much porn, or didn’t understand the concepts of commitment or fidelity.

In the process of writing this book, I also extensively interviewed other women, and each chapter ends with a tip section titled “Learn from My Experience.”

Image courtesy of Unsplash

How did writing this affect your personal relationship?

I started writing this book a couple of years before I met my husband. However, once we did meet, he was very supportive through the process. He knew how much it meant to me to be able to finish it. But I think the process of writing the book made me think more about relationships in general — and all the compromises and hard work that are necessary to keep them strong.

What are your favorite parts and passages in the book?

My favorite part is my beginning quote:

“There is so much talk today about ‘women power’ and women making it on their own. Listen, I knew I could make it on my own; I didn’t need a man to support me financially. But what about love! I realize that marriage may not be for everybody. I hear some women saying, “Who needs a man? I make my own money; I can go to a sperm bank.” I get it. I had some of those same thoughts when I was frustrated with the whole dating scene. But I wanted love, a connection, a family. That’s what I longed for, and I wasn’t stopping until I found it.”

What did you do to become an expert?

Let’s face it: if you do something long enough and become good at it, almost by definition you become an expert. There is no way to get a PhD in dating. But anyone who has been dating for 20 plus years is an expert. Spending years thinking about this and interviewing other women has brought my expertise to the next level. I wanted to tell my story but I also thought my experiences would help others and give them hope.

Why spend years of your life writing it and what were you trying to achieve?

In 1960, 60% of all Americans were married by the age of 29. That number is now down to 20%. I knew so many people who were searching for love and wanted a family as I did. I wanted to share my story so others could feel a connection and know they weren’t alone. I set a goal and I was not giving up until I achieved it.

What got left out in the final draft?

You can’t possibly put everything in the book. Whether you are a first time author or if you have published 20 books, there’s always going to be things that were left out and things that get edited before publishing. But I tried to leave out anything that might hurt another person.

What’s next for you? What are you working on now?

I plan on writing another book on relationships, possibly on being a step parent and/or the difficulties of being married. It’s very different from being single, and there are things that happen that you just never expect.

Is being a writer a gift or a curse?

I guess I will soon find out! There will always be people who are going to judge you and people who are going to lift you up. It is an accomplishment, no matter what way I look at it.

Is there anything you find particularly challenging in your writing?

Writing in general is a challenge, whether it’s putting your thoughts on paper and saying it the right way or editing and fussing over grammatical and proper phrasing.

Did you come across any specific challenges in writing Single and Not Settling?

My challenge was telling my story truthfully without singling out and offending people. This book was meant to be sympathetic and empathetic and to give people hope.

What inspires you to get out of bed each day?

I have a strong faith in God, and the fact that I wake up breathing is enough of an inspiration for me.

What is the first book that ever made you cry?

The first book that ever made me cry is My Sister’s Keeper

Tell us about your writing process and the way you brainstorm story ideas.

I like to jot down notes, even in the middle of the night (I am an insomniac). Most of my ideas come to my while I am lying in bed at night.

How has your environment and upbringing colored your writing?

I was born and raised in a Italian-American family on the north shore of Long Island, had a close family upbringing and always tried to look at life in a positive way even though I found myself over 40 and single. My parents taught me to always appreciate everything you have and also to realize that challenges are part of life.

If you were deserted on an island, which three people would you want to have with you? Why? 

One fictional character from your book

The characters in my book are not fictional; just the names were changed.

One fictional character from any other book

Robinson Crusoe! He knows everything

One famous person that is not a family member or friend

Channing Tatum, he is hot!

What’s something you are really good at that few people know about?

I’m a good cook, lots of Italian specialties along with others. I also teach sales and I’m told I’m a good motivational speaker.

Give us an interesting fun fact about your book.

My fun fact is that while I was writing a book about being single, I got engaged and married.

What qualities do you look for in a man?

Honesty, family oriented, hard working, respectful, fun.

Do you feel you were too picky?

Actually no, I know a lot of people who really are picky. I had one friend who wouldn’t date anybody who wasn’t drop dead gorgeous. She insisted that all her boyfriends have buns that were as hard as day-old Italian bread. I knew someone who broke up with a guy because he mispronounced a foreign item on a menu. But I think my personal problem was that I gave too many guys a chance or spent too much time with them when I should have been moving on. As we get older two things happen — we become desperate or have the “I’m fine on my own” attitude — so we can come on too strong or scare a potential mate away.

How did you know your husband was the one?

At first I actually wasn’t crazy about him because he texted me to go out. Having had some strange experiences with guys who preferred texting to real conversations, I had vowed that I was going to avoid “texters.” Then I said what the hell and we went out, had a great time, great chemistry. We both have been around the block; we were on the same page. We have respect for one another and we love each other.

What can people do to try to make meeting someone more pleasant?

· Keep an open mind. The person you think is not for you may actually be “the one”.

· Try everything available: dating sites, introductions, parties, charity events, sports.

· Singles tend to only hang with singles. Go out with your married friends.

· Don’t worry about what other people think. Remain optimistic. Remember, God helps those who help themselves, but it’s also his timing

How to survive the dating world?

· Stay true to yourself.

· Be realistic about what you want in a man. Don’t insist on the impossible.

· Have fun with everyone you meet, and remember it’s a learning experience.

The age-old question: who should pay on a date?

Women 40 and older are sandwiched between two worlds — the old world approach of the tradition dating where a man paid for everything, and the new world of dating where women now pay. If a man asks a woman out on the first date, he should pick up the tab. The women I know don’t mind paying their fair share once the relationship gets off the ground.

Tonia DeCosimo’s book Single and Not Settling: A Journey in Surviving the Dating World is available on in trade paperback currently and will be launched as an E-book on April 3. She also has a listing for her radio and book signings on her website as well.

Visit her website or follow her on Facebook and Twitter for upcoming news.

Originally published at

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