Dating Advice: 100 Bad Dates

100 bad dates? That doesn’t sound encouraging, does it? If you’ll read a bit more, you will understand why I start with that phrase and how it grew to organically form the basis of my dating image advice.

I am a media and public relations expert by trade and for years my friends and I (guys and girls) have applied my marketing, branding, media and communications experience to our dating lives. We have lots of stories! We call them Cock Tales. It has been a rollercoaster of marriages, divorces, affairs, break-ups, heartbreak, love, laughter, fun, great sex, horrible sex, silly sex, and lots and lots of first dates. My advice has always been based on my business experience in working for public relations firms, for corporate communications teams, and in consulting with over 100 small business clients.

When you launch a product or business, you have to plan on marketing that product to the appropriate target audience, because the goal is to build a brand that naturally resonates with customers and surprisingly that does not actually happen naturally. It never happens overnight and it never happens in a vacuum. The most sublime, subtle, quite brands have expended tremendous energy, money, and creativity in cultivating their look and feel. Why would you spend any less time cultivating your authentic self when looking for the love of your life?

Blame it on my MBA, but I know match-making takes both the art of human interaction and the science of experience to work. That’s why my advice has always been that you have to assume when you start dating that you will go on 100 bad dates. It takes time to perfect your authentic personal brand.

I went on 57 average-to-great dates the third time I found myself single and alone in the world until I met the one. I went on a couple dates after our first date but I knew the second we met (which I obviously did not say out loud for months because I know that makes me sound crazy!) even though I had dated so many other men that just did not quite fit.

I’m not dating anymore but I still give great advice to my friends. Now, I want to give great advice to anyone who wants to learn how our communications styles and skills are impacting our romantic lives in ways that we rarely notice. Your pictures, your social media posts, your texts tell a story – whether you are dating online or simply socializing with friends in the digital world.

People are not helpless in finding love and there are tons of dating and relationship gurus online. I love several of them and have learned a lot from a few of my favorite authors, bloggers, and dating experts over the years. You can check out my Dating Coach Resources page for free online content and advice and I will share my thoughts on why these free online resources are so important. Yes, they will likely pitch you some products and services if you sign up for their newsletters and if you have the money, I would say go for it! If I could I would spare no expense in cultivating my authentic self when looking for the love of my life.

The reason I am different than the others is that I know how to market and I know how to tell stories and I know how people communicate – especially when they want to influence others. The art of human interaction and the science of experience works in business and it works in real life. And as callous and brash and cold as that sounds, we have to understand that we live in a visual, technology-driven world. Even though our relationship happens in real life, the first connections, introductions, and conversations will most likely start on a digital platform and that experience will form the basis of that relationship. If you can master the art and science of cultivating your authentic self and your most sincere desires online, you will increase your shot at being lucky in love.

Izaak Walton said, “Good company in a journey makes the way seem shorter.” I would love to be your good company on this journey. Not because I know where the journey will end, but because I know that spending time cultivating your authentic self when looking for the love of your life is so worth it. Yes, even your soul mate needs some marketing to get things started and a great coach can help you believe in yourself and thrive in the dating world!

You probably have lots of questions and I would love to answer all of them. Sign up for a 15-minute phone consultation using the Get Coached form or you can review my brief Dating FAQ. I get lots of interesting questions, so check back for updates.

When a great coach is available to help you develop your talents and skills and to create an environment where you believe in yourself and thrive, anything is possible. If I can find someone that I call “the one” you can too. If I can say with confidence that I never want to date again, you can too. If I can know for sure, that if something horrible happened and I did end up single again, I would be ok. I would just start again someday (after drinking it out with my girls) and begin the process of 100 bad dates.

With kindness, humor, tact, and honesty, I will help you to set goals, make practical and tactical decisions, identify your strengths, tell your authentic stories, help you focus on having fun and ensure that you master the art and science of cultivating your authentic self and your most sincere desires online – all while navigating the often wild and ridiculous dating scene.

My gift is shaping stories and with 25 years of marketing, merchandising, and publicity experience, I can help you develop your individual communications style and walk with you on your journey to find love, taking the time to educate you on the relevant tools (online dating can be so confusing!) and social options while listening to your specific challenges, experiences, and needs.

While understanding that “winning isn’t everything” and dating is not a game, I can work with you to put in place a helpful process to get through the technology and sometimes silly or stressful parts of dating while understanding what motivates you to connect with others or to find The One.

Know that as a coach I am tough! If you’re just looking for hook-ups and lie about it, or are looking to cheat, you will not be supported and you will get cut from my program. However, if you are genuinely interested in meeting new friends, finding dates, dating seriously, or getting married, I truly believe that my insights to communication, engagement, presentation, event planning, branding, public relations and marketing (yes, even your soulmate needs some PR to get things started!) will get you closer to your ideal scenario.

If we get a chance to work together, I can assist you with the following:

  • Custom Communications
  • Dating Conversation Skills
  • Dating Etiquette
  • Event Planning
  • Image Consulting
  • Online Profile Development
  • Social Media Skills

I would love to hear your thoughts! If this all sounds awesome to you, let’s connect! You can sign up for a 15-minute phone consultation using the Get Coached form and we’ll get you dating better tonight! 

If you have a great dating story, I would love to hear it! Send me a note via email at and we can post it on the blog.

~ Coach JJ



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