in: Dating & Relationships

A Step-By-Step Guide to Dating Fearlessly

Step out of your comfort zone and start dating fearlessly. This month Dr. Hick shares how and it could lead you to live bigger and bolder than ever.

In last month’s installment of Fearless Living in 2015, we explored how loving yourself fearlessly—including all of your flaws, imperfections, and quirks—could change your life. I hope that taking time to reflect on a daily and ongoing basis provided new insights into your current blocks and helped you envision how life-changing loving yourself can be. Furthermore, I hope this focus got you fired up to plan and practice loving yourself fearlessly!

If you are beginning to feel a little uneasy, like your universe is being shaken up a bit—this is an excellent sign. It means that you are starting to look at the world, yourself and your relationships a little bit differently. And with difference there is often some initial discomfort.

Now that we’ve got the ball rolling on the year of Fearless Living, with an introduction and loving yourself, this month’s installment will explore dating fearlessly.

If you’re like many of the people I help and talk to, dating seems to be a revolving door of not-quite rights, let-downs and in some cases, utter disasters. Date activities seem to be of the coffee, drink or dinner varieties, with the occasional unique art walk or cooking class.

Imagine for a moment that it could be different, that you could be different, that he/she could be different. Imagine that it could be better, more interesting, more engaging.

Do you dare to imagine how it could be if you and your date approached dating with fearlessness? If you let your guard down, you were authentic and you stretched the way you dated?

Dating Fearlessly

Now, for those just tuning in, January’s edition of Living Fearless reviewed what fearlessness is and is not. Fearlessness does not involve meeting at his/her place for the first (or second) date, or flying to Vegas with someone you barely know. Nor does it mean bearing your soul to your date before the waiter even has a chance to present the dessert menu.

Fearless dating is about acknowledging your dating fears, pushing past the annoying insecurities that get in your way and challenging yourself to take growth-worthy risks in your dating adventures.

Playing it Safe?

In dating, most people lean towards the safe edge. You play it safe by frequenting your usual spots to try to meet people, by texting instead of having a conversation by phone, by planning dates at places you know well and can thus in some manner orchestrate the date to go a certain way—no surprises.

Why is everyone so afraid of surprises? Yes, surprises can be a little scary and force you to think on your toes, but they can also bring about wonderful possibilities you never considered. If I were to step out on a limb (also scary) I would say that most people are afraid of surprises, of stepping out on the ledge, because it means we have to face our fears.

What Are Your Dating Fears?

Fears. We all have them, for one reason or another. If you recall my previous piece on exposing old wounds to give love its best chance, you’ll know that regardless of how “normal” or “abnormal” your childhood was, everyone has wounds—unsettled feelings about hurtful, confusing or painful experiences—that can rear their ugly head in adult relationships. Unless you recognize what they are and address them, they typically get reenacted and can compromise what could be a wonderful relationship.

The same goes for fears—everyone has them and they typically stem from early experiences, and sometimes, later experiences, with significant people in your life. Sometimes they involve parents divorcing and having difficulty trusting that relationships can last as an adult or feeling that all conflict is always bad. They can come from being bullied for being yourself in middle school or feeling as if you always have to put on a mask to be accepted as an adult.

Regardless of the source of your fear, I’m betting that you have at least one or two and that they may be getting in the way of finding love, of dating fearlessly.

Let’s Get Honest…

Ask yourself, “How do I play it ‘safe’ in dating?”

  • Do you fear that you will be rejected so you date people who minimize your risk for rejection?
  • Do you fear that you won’t know what to say so you plan a date with little room for conversation? Or, do you have a list of topics and seldom stray from it for more authentic discussion?
  • Do you feel as if you are not worthy unless you date a certain “type” of person?
  • Do you date others with whom you feel you can easily navigate the situation, or with whom you feel in control?
  • Do you only go on dates in which you can “dress the part” and obsess about looking perfectly to impress him/her?
  • Do you go to “safe” date spots, such as a restaurant, favorite coffee shop, the bar down the street from you?
  • Do you select dates based on physical or materialistic qualities rather than looking beyond to shared interests, spiritual compatibility and emotional characteristics?
  • Do you have a “list” of 20 characteristics that you use to make dating decisions, instead of five of the most important?

Are there other fears you have about dating, love, relationships, etc. that you compensate for in some way? Could these ways be holding you back?

Conquer Your Dating Fears

The way I see it, if you take a chance to recognize and conquer your fears with the chance that you may date differently this year, why not try it? Here’s an action plan for the next step in Living Fearless in 2015.

Here’s your goals and action plan for March:

Week 1: Identify (through journaling or other medium of your choice)

  • What are your fears—list them all.
  • What practices have helped you compensate for or avoid your fears?
  • What are you willing to change to face your fears and practice differently?

Week 2: Process on your own

  • Create and work on three goals of how you would like to proceed with fearlessness in mind.
  • Write a letter to yourself—How are you going to practice fearlessness in dating? What are you looking for now that you are putting your fears aside?
  • Write a letter to your future date—How are you going to practice fearlessness in dating and what do you hope from him or her in this regard?
  • Use imagery or a visualization exercise to practice fearless dating in your thoughts.
  • Create a vision board with how it would look like to date fearlessly.

Weeks 3, 4 & Beyond: Practice with others

  • Work on the three goals you created.
  • Expand your search—look beyond your typical places and typical pool.
  • Enrich your date activities—get outside your own box.
  • Practice new ways of being and relating.

Practicing fearlessness in dating may not lead you to Mr. or Mrs. Right right off the bat, but with each small step you take to push beyond your fears, you will be dating differently and will be making internal changes that will help you become a better version of yourself—the most fearless version of yourself who can welcome the surprise of a bigger, bolder life than you have ever known before.


[Image: via J.K. Califf on Flickr]

About the Author:

Kristen Hick

Kristen Hick, Psy.D. is a Clinical Psychologist who specializes in the area of awakened dating and healthy relationships. She is the founder of Center for Shared Insight, a private psychotherapy practice in Denver where she and her clients focus on Individual Relationship Therapy. Dr. Hick’s expertise lies in helping individuals create healthy, meaningful, and loving relationships with others through healing, strengthening and transforming their most essential relationship, with themselves. When not helping clients fulfill their personal relationship goals, she enjoys the Colorado outdoors, capturing life through photography, practicing yoga and hopes to one day manage her first unassisted headstand. You can connect with Dr. Hick on her site, Facebook or Google+


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