Why Dating Should Be Messy!

Why Dating Should Be Messy!

Okay guys I swear I’m going to write that post about online dating but life has been so crazy that I haven’t even looked at my dating apps in weeks let alone managed to go on a date. Dating is not top of mind at the moment!  Lucky for us, Clara, our (sometimes) resident dating expert is back for another post. I really took a lot away from her post as I definitely have fallen into pretty much all of the traps she mentions. My dad also drilled it into my head that dating should always be easy in the beginning. And it never is. So it’s nice to have someone recognize that things aren’t always easy and messy is okay… good, even! Thank you Clara, for a wonderful post!

There’s this wonderful passage in Sherry Turkle’s latest book, Reclaiming Conversation: The Power of Talk in the Digital Age, where she describes dating apps as “bringing the promise of a business-like crispness to falling in love.” It goes hand in hand with the idea that when something works, it just works. It’s the notion that when a relationship is meant to be it just flows….effortlessly. No one’s really talking about the hard but inevitable challenges that are inherent to building intimacy and connection in any relationship.

One of the main philosophies that informs my work and dating strategy is the following:

Dating isn’t hard because men are inherently assholes. Dating isn’t hard because the apps are bullshit. Dating isn’t hard because men don’t want to settle down. Dating is hard because it’s an emotionally complicated endeavor, the ultimate goal of which is no small feat: A deep and meaningful connection with a person you respect, admire, and love, and the desire to build something great together. It takes grit, courage, humility, forgiveness, vulnerability and endless self-compassion. No tip, trick or rule will trump that reality.

As career-driven, hard working, generally badass women (which I know Grace’s crew to be), we often find fault in any kind of messiness. We pride ourselves on finding the most efficient and effective way of figuring something out—whether it be our careers, working collagen protein into our diets, or making it to our 6 am spin class on the regular. So naturally, we apply this some mode of thinking to our dating lives. That’s why I love Sherry’s wording. We try to to-do list our way through dating. Get on app. Create profile. Start swiping. Go on first date. Rinse. Repeat.

They’re also positioned to us in this way.

Your pathway to meeting someone special sits amongst your calendar, online banking portal, Mind Body app, and everything else you use to organize and optimize your life. It’s implied that this whole meeting people thing? It should be easy. It should just flow. And if it isn’t, it’s something you’re doing wrong.

I really don’t mean to vilify the apps. I merely point this out to reflect on the environment and expectation we’ve created around dating in the digital age. And awareness is always the first step in creating change. So if we start to warm to that awareness – the idea that dating should be messy, how can we start to work with that? How can we have it support our dating endeavors, rather than make us feel like we’re doing something wrong?

First and foremost, we can remove the pressure we’re placing on ourselves.

If dating feels hard, scary, unpredictable, confusing, or any other emotion you’re feeling guilty about, know that’s normal. It’s more than normal! It’s to be expected! Especially if you’re seeking something long term and meaningful (as most of my clients are), this is a significant thing. It’ll be a little odd if it just went all according to plan, no? Ask anyone who’s entered a serious relationship and there’s likely a clunky story of how the relationship got there, but we so often focus on the more magical elements because we tend to romanticize the past.

Next, get curious.

What behind the messiness of dating makes you most uncomfortable? Is it the fear of rejection, the inability to control an outcome, the larger fear of getting hurt? What’s really there? That’s the more valuable piece of information. That’s the thing you can start to work with and explore (what I call “root problems”) that’s acting as a block in your dating life. It’s not the apps. It’s not men in general. It is not your nagging family member…and so on.

In short, find freedom in the messiness. Don’t equate a smooth dating process with success, or the lack thereof with the idea that you’re inherently bad at dating.

Alrighty, I hope that relieves some stress! For my local gals, I’m giving a talk tonight on a healthier approach to dating. The event is technically sold out. But if you’d like to come, I have a few spots to squeeze some people in :). Just message me over on Insta. Xx Clara

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  1. Emma:

    This was SO refreshing and just what I needed to hear. Thank you Clara! And Grace 🙂

    4.12.19 Reply
  2. I love these posts by Clara! I’m in a long term relationship but it’s nice to read up on what the dating scene is like now.

    Charmaine Ng | Architecture & Lifestyle Blog

    4.12.19 Reply
  3. DAMN this was good. Especially the part in how we are so quick to find fault in any messiness—so true, especially in how we (I?) judge ourselves.

    4.12.19 Reply
  4. Ashley:

    Dating someone should not be scary!!! I went through horrible dating experiences, being verbally and sexually abused by guys. Eventually I learned how to quickly spot abusive people, and I avoided them. I found a sweet, kind, and humble guy on Facebook and went overseas to marry him! We now have twin babies and are incredibly happy. Yes, we had a few issues to work through as far as cultural differences, but I’m so thankful I didn’t settle for anyone who was an overall angry person.

    4.12.19 Reply
  5. Melissa:

    I needed to hear this today! Great read!

    4.12.19 Reply
  6. Denise:

    So true! It’s not easy but when it works it kind if is, such a balance but not easy to figure out, not helpful but if it feels right go with it and you will know. With age I have finals realized if the feeling isn’t there you move on with everything not just dating! Trust your Self.

    4.12.19 Reply
  7. Lisa Autumn:

    Girl this was an amazing post! Well done!

    x Lisa | lisaautumn.com

    4.13.19 Reply
  8. This was such an interesting read! Thank-you both for sharing this, so refreshing!

    I hope you have a great Saturday!

    4.13.19 Reply
  9. Deb:

    Hello my name is Debbie. I am a new 56 year-old widow. I am average weight attractive dress youthful outgoing have hobbies even a small dog. Yet I am very lonely. I joined our time and all I do is talk to men via text and haven’t gone out in the date yet? I also joined meetup groups mostly women having fun but haven’t met anyone to date. What am I doing wrong?

    4.14.19 Reply
  10. Octavia:

    When you’re in a relationship there are always going to be hard days, weeks… But if it’s hard at the beginning forget it. It’s not going to get better. Sorry, but youre Dad is right.

    4.15.19 Reply
  11. MarciaMarciaMarcia:

    I got married eight years ago, at age 40. I still remember in our premarital counseling (required by our church) our therapist noting that even though our connection may feel very right, we ultimately come from different tribes, and there will come a point where it becomes starkly clear that our tribes do some things differently. This isn’t good or bad, just different, but if we don’t deal with the differences and accept and acknowledge them and figure out a way to merge or get around those difference, problems will result. It was SO TRUE. And it took some hard work and lots of honest communication to figure that stuff out. I’ve heard it said often that the first year of marriage is the hardest, and I think if you’re doing it right, it should be. I’m so grateful for the stuff we hashed out early on, because it led to so much less messiness now. I love this post, even though it’s talking about dating and not marriage – I think the point is the same. Real honesty and intimacy, the kind that leads to lasting connection (or the realization that lasting connection isn’t in the cards) is messy. And that’s not a bad thing, that’s just part of the journey.

    4.15.19 Reply
    • “Real honesty and intimacy, the kind that leads to lasting connection (or the realization that lasting connection isn’t in the cards) is messy. And that’s not a bad thing, that’s just part of the journey.”

      Full body YES to all of this Marcia! xx

      4.25.19 Reply
  12. I love the ending of this article where you find the root cause of the issue and find freedom and embrace the messiness. I think that you can apply this beyond dating


    4.16.19 Reply