How to Survive the Grey Area of Dating.

How to Survive the Grey Area of Dating

I have been obsessed with all of Clara’s posts so far (especially her post on why dating should be messy) but this one may be my all time favorite things she’s written here. Because the grey area of dating is the absolute worst. When you like someone but aren’t sure if they like you back, when you want to have a talk but don’t want to “scare them” away, and so on and so forth. As always, Clara delivers beautiful, thoughtful advice that I think we can all relate to/learn something from.

This past Sunday morning, as I was frosting a massive coconut cake for my family Easter celebration (as one does), I had Brené’s new Netflix special keeping me company in the background. She dropped knowledge bomb after knowledge bomb (as she does), but the one that really stuck with me was the following:

One of the biggest barriers to courageous leadership is tough conversations.

Swap out leadership with dating or relationships, and it rings just as true.

I have a wonderful crew of single gal pals who are always chirping at me about what I should write about next when it comes to dating in the digital age. It’s wonderful. I consider them my muses. But the one area they’ve repeatedly referenced that I’ve consistently avoided is the grey area. The in between. That period in dating when things are going well but you’re not sure what you are or where things stand or where they’re going.

Your first few dates have been great but the days in between are agonizing.

There’s no next hang on the calendar. You’re feverishly analyzing every single text — the timing, the frequency, the substance. More often than not it makes you feel even less certain about the situation. You want to have a conversation about where the other person’s head is at, but you’re afraid it will scare them away. You’ve sent screenshots of conversations to all your besties, begging, pleading (insert all the prayer emojis) for them to magically read what’s behind his texts. Maybe they’ll somehow see his “How’s your day?” as “Btw I’m totally ready for committed partnership. Wanna do this thing?” Yeah, no. God, if only.

Living with this ambiguity can make you feel like you’re going absolutely insane. One said friend-muse was getting so anxious about a guy situation it was literally waking her up in the middle of the night.

At her wit’s end, she asked, “Can you just break down how to deal with this period with some tangible steps?” Suggesting she go to her love interest and say, “Hey, I’ve had so much fun getting to know you. I really want to see more of you. But I wanted to check in— where do you stand when it comes to us?” isn’t exactly a simple step. It’s the exact opposite. It’s a really loaded situation. (But btw, if you feel comfortable saying just that, than you most definitely should say just that. Power on. And if not, start practicing in all aspects of your life. Family. Work. Wherever.)

Unfortunately, the only way through the grey period is……(back to Brené)….tough conversations. Yep.

I can tell you that your dating life (probably entire life) will become infinitely better the more comfortable you are having the tough conversations and possessing the ability to not let them totally rock you, whatever the outcome. But as you’re warming up to the idea, here are some tactics in lieu of fully baring your soul:

1. Understand that the anxiety may be a sign that you’re giving much of your power away by thinking that the other person’s actions completely control the situation (both the reality of it and your emotions).

Start practicing reframing that narrative – you have a choice in every interaction to gain the clarity you’re seeking.  As an antidote, get honest with yourself both about how you feel about this person and how you feel about the situation. This is more than “I really like him.” It’s “I like this, this, and this specifically. This gives me pause. This I have questions about” and so forth. Just doing this (ideally writing it down, if not mustering up the courage to gain clarity on it directly) is a way of taking your agency back.

2. Acknowledge what’s really coming up is that you’re uncomfortable.

Life is an endless string of uncomfortable situations and the only thing we can do is practice getting more comfortable with discomfort. So meditate, go for a long run, unload to your bestie— do whatever it is that’s going to help warm you up to a tough conversation. It doesn’t matter the salve, just know leaning into discomfort will solve 90% of the hard stuff in life, btw.

3. Get ahead of the anxiety and discomfort altogether by setting expectations from the get go.

I did this by noting in my online dating profile that I was “seeking something meaningful.” If your first reaction is, “But what if that scares someone away?” Great! And think of it less as scaring someone away (hello scarcity mindset), and more so as creating a very valuable filter. Because that’s exactly what it is and will save you all of this grey area heartache down the line, ultimately opening you up for something better, sooner.

This period is brutal. Know you’re not alone in that. I had a client the other week brilliantly equate it to falling—like literally falling down. In the process of falling for someone you lose your equilibrium, your center— just like when you fall down.

So do your best to exercise endless compassion for yourself. You’re doing just fine.

Xx Clara

Clara Artschwager is an NYC based Modern Dating & Relationships Coach who specializes in helping career-driven women shift their approach to dating. Her work has been featured in The Cut, Well+Good, Man Repeller, Girl Boss Media, and more.

Leave a Comment

Leave a Comment


  1. Charmaine Ng | Architecture & Lifestyle Blog:

    I learn something new about dating every time I read your posts, Clara! Yes, compassion, always!

    Charmaine Ng | Architecture & Lifestyle Blog

    4.26.19 Reply
    • Clara Artschwager:

      I’m so glad! xx

      4.29.19 Reply
  2. Olga:

    Love this so much, couldn’t agree more! I’ve avoided tough conversations like this in the past and it didn’t work out well!


    4.26.19 Reply
    • Clara Artschwager:

      So glad it’s clarifying some previous experiences, Olga. xx

      4.29.19 Reply
  3. A:

    Heh, the conversations I’ve initiated are more like “I am not interested in a committed partnership. Do you want to keep doing this thing? I’m having fun.” And the only time I’ve sent screenshots to a friend was when somebody said, in a failed negging attempt, that feminists have too much baggage and are bad in bed.

    4.26.19 Reply
    • Clara Artschwager:

      At the end of the day, it’s all about communicating your needs. Major points for doing so! xx

      4.29.19 Reply
  4. Margeaux:

    Thanks so much Clara for this insight! I love reading posts like this and realizing I’m not the only one with these thoughts and feelings! So reassuring to know many of us are experiencing the same thing!!

    4.27.19 Reply
    • Clara Artschwager:

      You’re most certainly not alone. We’re very VERY much all experiencing the same things 🙂 xx

      4.29.19 Reply
  5. Lisa Autumn:

    Oh I loved this post! Such good advice 🙂

    x Lisa |

    4.28.19 Reply
    • grace at the stripe:

      Thank you Lisa!

      4.28.19 Reply
  6. Theodora:

    LOVE the point about getting comfortable having tough conversations. This is something I’ve been entirely leaning into in my life lately and embracing really and truly being OK with the outcome. As someone who completely steered clear of these convos for the first 36 years of my life, it feels SO empowering to have them and take more control over relationships with friends and family. And it really is true that the more you practice, the easier they get. Never *easy*, just easier.

    4.28.19 Reply
    • Clara Artschwager:

      ” Never *easy*, just easier.” YES!!

      4.29.19 Reply
  7. Tabitha:

    Honestly, if you’re feeling anxious don’t ignore that and give it a pass in the name of the grey area. I gave too many men this benefit of the doubt over the years. When I met my husband, there was zero grey area. It was an instant connection and we always had the next date on calendar. You deserve that, and I recommend holding out for it.

    5.4.19 Reply
  8. Dianna:

    Wow! Thank you so much! Googling, I honestly did not know if this grey area was real! I feel so stuck in it, and want so much to move out of it! It was like you wrote my heart into paper! Thank you again for giving me a way to look forward!

    1.17.20 Reply
  9. Corie Dunstan:

    Good article. I really needed this. Helped me to get clarity.

    7.31.23 Reply