The best way to ensure a second date is your ability to walk away from the first date.

Let me explain this in entrepreneurship terms, as I like to do.

When I first started out in my dating coaching business, it was a challenge to get clients. When somebody did come along, I’d bend over backwards to get them to sign up with me, even if that meant compromising my methods, giving away too much for free, or putting up with less than desirable behavior.

I want nothing more than to help people create love in their lives (that’s why I do what I do!), but in order to be a living, breathing, thriving business, I learned how to create boundaries and trust in myself. When you’re just starting out in a venture, it’s natural to want to morph yourself into a pretzel to be what you think the client or customer wants you to be just so you can get their approval and get them to want to work with you.

But as I grew as an entrepreneur (and coach), I started to realize I didn’t need to be everything to everyone.

I started to draw a line in the sand about what I would do to grow my business to the next level. If that meant losing a potential client here and there, so be it. 

Of course, maturing in this way in an entrepreneurial venture doesn’t mean you don’t experiment with new ideas (you must!) or that you shouldn’t listen to feedback (you should!), but it does mean you learn that you don’t have to become someone you’re not. Ironically, I’ve found that being confident and comfortable in my own skin with prospective clients, without being paralyzed by the fear of scaring them away, has helped my business grow! And it’s also weeded out the clients who just aren’t ready for a life-changing coaching relationship.

Read everything above this line again and frame it in terms of your dating life.

You will see a powerful lesson emerge: letting go of attachment to outcome.

A lot of women bemoan the fact that they have no trouble being invited on first dates but have difficulty being asked for a second date, especially from men they like. A simple way to change that is to apply the aforementioned strategy to your dating life, which, ultimately, is a change in your mindset.

When you go into a first date experience with an attachment to outcome (“I’ll do and say whatever and be whoever to make this work; I have to, because he’s such a good catch and it’s so rare I meet men I like”), you end up not being yourself.

You morph yourself into that pretzel. date1

You can’t relax and enjoy the present moment, because you’re constantly in your head about what you need to do and say to “make the sale.”

You lose confidence in who you are and the fact that, you know what, you’re a great catch, too! So, instead of bringing to the table a woman who is confident and comfortable in her own skin, you bring forth a woman who is unsure of herself, a woman who oozes insecurity. Your dates pick up on this energy.

But what if you could shift this mindset? What if you could walk into your first date experiences without an attachment to the outcome and with the ability to walk away even if your attraction level is sky-high? What if you were to walk into a first-date situation with a different focus?: “You know what, I’m a great catch, too; I’m going to be myself and I’m going to be friendly and upbeat, and if this guy isn’t buying what I’m selling so be it, because there are plenty more fish in the sea.”

Now that is a powerful way to date – let’s call it fearless dating. Adopting this new mental model will change the way you approach early stage dating situations. And I guarantee you that shift will help ensure more second dates.

When you de-pedestalize your dates in this way, realizing that you are on the same exact level, because, after all, you’re both just human beings looking to make a connection, you’ll stop worrying about what you have to be, say, and do to land the second date.

Neely Steinberg is a dating coach and founder of The Love TREP®. Her book Skin In the Game: Unleashing Your Inner Entrepreneur to Find Love is available on Amazon.  The Workbook for Skin In the Game is also available on Amazon.




Neely Steinberg is a nationally recognized dating coach and founder of The Love TREP®. She has been featured in/on countless media outlets, including Fox-25, Huffington Post, Cosmopolitan, Men’s Fitness, Boston Magazine, the Boston Globe,, and JDate, to name a few. Her goal as a coach is to help smart, savvy, professional women of all career backgrounds become the CEO, founder, and enTREPreneur of their dating and love lives so that they are creating the relationship they truly desire, instead of waiting for some elusive Prince Charming to find them. She lives in Boston with her husband. Her first book is entitled “Skin In the Game: Unleashing Your Inner Entrepreneur to Find Love.” You can read more about her book and workbook at:


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