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Dating Never Works…Until It Does

100 Lessons from 1,000 Dates

Dating never works book

So…what’s this book about?

Why does dating never work? Because it’s not supposed to—that is, of course, until you meet the last person you’ll ever date.

It took Zack Oates over 1,000 dates to find his wife and he has 100 pieces of advice to help you do it in less time with more fun. Dating Never Works…Until it Does will help you get from first contact, to great dates, to overcoming heartache, and all the way to a happy marriage.

It is full of practical steps, crazy dating stories, and hilariously accurate pieces of wisdom to give you a boost at any stage of dating.

Pull up a chair, grab some ice cream and come have a chat with a guy who has been writing about dating since 2008. You’ll laugh, you’ll cry, and in the end, you’ll realize that for the single, dating isn’t broken it–it just hasn’t worked out…yet!


I wish I had this book when I was single. Zack is able to use his 1,000+ dates to help others to navigate the dating field from both the emotional and practical side. It is a great read. Recommend!”

Steve Young, Hall of Fame Quarterback, Married at 38

“This book is a great combination of personal experience, wit, and practical wisdom (did I mention wit?). Zack has an uncommon perspective offered to anyone who finds dating to be a challenge and would like to have a better experience. Read it, enjoy it, apply it, live it, love it.”

Klayne Rassmussen, PhD, Marriage and Family Therapist, Author of The FrogBuster

See why NFL Stars, Studio C Celebrities, Marriage and Family therapists, Award-winning Directors, Entrepreneurs and so many others (including his grandma) have endorsed Zack Oates’ breakthrough book on dating and relationships!

Read more endorsements here.

Who is this book for?


While it is great for single people, it also helps couples be grateful for what they have, gives advice for sparking the relationships, and provides tools for talking with their single friends about dating.

So who is this guy writing a book?

Zack Oates is an entrepreneur, husband, father, hot tuber, and author (but not in that order, necessarily). He went on over 1,000 dates with hundreds of women before he met his wife—and would appreciate any advice on how to make sure that his next 1,000 dates are with the same woman.

He grew up in New Jersey in a home with rockstar parents who showed him anything is possible—even a happy marriage. His dad is a three-time Super Bowl champion and his mom is a model; but admits that he was given his dad’s looks and his mom’s athletic abilities.

In addition to earning his MBA, he has started seven business, voted Top 100 Entrepreneurs, rung the NASDAQ bell, and has been featured in numerous major news publications (Wall Street Journal, NYTimes, Wired Magazine, Mashable, etc.) for his ventures. He is currently CEO of Ovation, a chat platform for restaurants and retailers. He has also started an international nonprofit working with victims of domestic violence. He has written hundreds of dating, relationship, and inspirational advice to hundreds of thousands of readers at

He has been to almost 50 countries across 6 continents, but is more proud of going to over 100 hot tubs. He has a love-hate relationship with running, in that he loves the thought of it, but hates doing it…yet somehow he has limped across the finish line for one marathon and dozens of half marathons. In his spare time he can be found on an adventure with his wife and kids or staring at a map planning the next one.

If you would like to book Zack to speak at a youth or single adult fireside, dating conference, or other event, please contact him here.