100 dates

Our romantic lives have a unique way of exposing us – our vulnerabilities, our flaws, the things we hold most precious, the frailties in our ability to love – in ways that other types of relationships just don’t. If you think too hard about this, it’s actually quite scary and easy to see why no one would move forward at all!

The problem is, that’s not how we’re designed. We are made for relationships.

I came of age in a time when an evangelical book called “I Kissed Dating Goodbye” taught that there is one right way to pursue relationships: courtship with the sole intent of marriage. I’ve seen people use this mentality as a wonderful excuse to get comfortable in their fear of romance, never trying anything and therefore never learning anything either, or simply blaming “dating” when they did try something and it didn’t work. I myself felt afraid that I would be doing something wrong by dating without knowing for certain that it would or could end in marriage, or that I would be deemed frivolous for this desire. This caused me to live a relatively risk-free existence and, consequently, one where I was always alone.

Then 2013 was the scariest year of my life. But surviving challenged me to determine my priorities. I made an important decision: Fear is not allowed to dictate my life! I committed to taking more risks and I dove in headfirst. This worked out great for my career; with romantic relationships, however, I was on shakier ground.

Having not experienced much in the past, I really felt my lack of relationship knowledge. Someone hurt me, and I hurt someone. One thing I discovered is that things surface in romantic relationships that you won’t learn in regular friendships or community. So I decided I would go on 100 dates to learn – about men, about myself, about love and its process. I’m chronicling my adventures and conclusions on a blog called, 100 Dates.

100 dates los angeles

Some wonder if I’m cheapening dating. My mother worried that maybe I was using people until she read what I wrote about the dates and understood my heart. I believe that in my execution, I’m (imperfectly) demonstrating value. My intent is to engage each man in an honest way. To me, devaluing a man looks like immediately trying to turn him into a husband, because that’s just filling a blank without regard for who he is. Yet, I am searching for a partner, so there is no bait and switch. My expectation is that I will grow closer to the woman I need to be for my future partner; my hope is that maybe I’ll meet him.

I’d like to share some of what I’ve learned so far in hopes that you’ll find it encouraging:

Dating is okay! It’s time to stop feeling guilty. Sometimes women get stuck because we don’t feel our role is to pursue, but we don’t know what else to do. A big part of our role is intentionally making it known that we are open and available, whether through apps or asking friends for set-ups or any other means. In this way, we can be active without taking the masculine role.

It gets easier! Dating has ups and downs, but as an overall trend, my nervousness has diminished significantly.

Everyone has something valuable to teach if we’re willing to pay attention.

Dating has given me a stronger sense of my own boundaries and the confidence to uphold them. And I’m learning to trust myself more. Our guts and instincts are designed to protect us and are different from fear.

Rejection can be okay. I have experienced it without feeling devastated or questioning my own worth. Rejecting someone else is also okay, so long as we do it in a way that is both honest and kind.

Dating is allowed to be fun! Sometimes fun creates a pathway to connect. While it takes time to develop a relationship and to truly know someone, there’s often joy in simply being present with another person.

Through this process, I’ve started to identify what doesn’t work for me, and I’m learning to see it more quickly and deal with it more graciously than I have in the past.

It’s helpful to let go of the idea of soul mates or any equivalent notion. Whether right or wrong, this concept absolves us from our responsibility in two ways – one, it encourages passivity in the search (and then we are left wondering why nothing ever happens), and two, it lets us avoid doing the work required of an actual relationship. We can blame “it’s not meant to be” for anything that doesn’t work instead of examining our own shortcomings. This robs us of an opportunity to grow.

 Heartache is a real possibility, and these things aren’t comfortable. But they are good.

Somewhere between “I Kissed Dating Goodbye” and Tinder rendezvous is healthy dating. Healthy dating is research that reveals who we are and what we’re looking for, which helps us to identify it when it comes along. But, just because it’s healthy doesn’t mean it’s easy. In fact, because it’s healthy, it will stretch you — it involves courage, risking, and surrendering control. Heartache is a real possibility, and these things aren’t comfortable. But they are good. While I can’t promise you a particular outcome, the one thing I know is that we have the power to transform our dating into something healthy and beautiful.

What are your thoughts on dating? How has it stretched or challenged you in a healthy way?

Images via Michelle Madsen


  1. I came across this blog article today and I appreciate your thoughts on how it helps to approach dating with open-mindedness, self-awareness, and curiosity– yes to that.

    But the language that you use in your opening paragraph is concerning: you use the phrase “chinks in our ability to love”. The word “chink” is a racial slur that’s often said in spite against Asian Americans (who look East Asian) like myself.

    Yes, the dictionary definition of “chink” means a narrow opening or crack, but out of all the other words you could’ve chosen (there are two in that definition: opening, crack, hole…) you used a racial slur. It’s quite the flattening, disempowering use of language. So disheartening to see, especially in such a positive online space like this.

    1. Hi, Evelyn —

      I’m Jen, the writer of the article. I saw your comments, and I’m so sorry that I hurt you with my use of language. That was definitely not my intention. When I wrote the article, I chose that phrase for its association with the expression “chink in the armor” and the way it connotes a certain vulnerability through weak spots, not actually realizing that in a separate context, the word is also a racial slur. The word has been replaced, and again, I am sorry for the offense that I caused.


  2. Just stumbled upon your post here, and decided to check out your 100dates blog… I’m loving it. So refreshingly honest, and I can relate to where you are coming from/what you are looking for, from a spiritual standpoint. I am learning more about myself and my own dating tendencies, just by reading your words. It’s strange and comforting to discover your own quirks and fears living in someone else, as they write about their own life experiences; it’s connecting in a way. I will definitely be following your journey!

  3. I love this article! I also was thrown “I kissed dating goodbye,” along with a few other courtship books that shamed dating, and I have many, many friends who are young and just so happened to marry one of the first people they have dated, however that isn’t everyone’s story. It often creates more heartache to put that pressure on two people, and keeps you from learning from them and growing as an individual as vulnerability pulls back the layers of your own heart and insecurities.
    One couple gave me the advise on dating, that as long as you position your heart in the relationship for the person to be a better for knowing you, than the relationship, whether it ends up in marriage or simply a nice date, it’s worth it.
    That has been my cornerstone in dating, just to to treat men honorably, live life wholeheartedly, and take risks.

  4. Dating has always seemed like a daunting experience to me, especially now in the time of Tinder and Coffee Meets Bagel, etc. I’m definitely a hopeless romantic so I put a lot of pressure on what I think it should be like. Your perspective is a refreshing way to look at dating and one that I think will lead to more meaningful relationships. I’m really looking forward to reading about your 100 dates experience!

  5. Refreshing… I’m walking through a similar journey in my own thoughts and approach to dating. Let’s be honest, I don’t want to just have an ability to date well, I do want to meet the man I will marry. But I’ve found as I approach dating [or a date] as an opportunity to meet someone new, find out about a person, their perspective, their view of the world, my life is richer and I’m impacted if I allow it. There is beauty in the pure enjoyment of another person. AND that takes pressure off anything initially. I want a foundation for a solid romantic/marriage relationship to be friendship anyway! Thanks for your honesty and sharing where you’re at. I hear ya girl!

  6. My thoughts on dating is that it’s wicked tough! Out of all of my single friends, I certainly make the most effort to put myself out there and to be open to whoever I may meet, but consequently this means I face much more rejection. I go through cycles of positivity and excitement about who I could meet and then when something doesn’t pan out I’m left wondering what in the world I did wrong. At this moment I’m in the latter, so it was great to read your encouraging post. I’ll be sure to follow along with your 100 dates blog and can’t wait to see how it goes!

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