Courage in Dating

You Can Date Better
7 min readNov 30, 2023

Boldness be my friend. Arm me, audacity, from head to foot.” — Shakespeare’s Cymbeline

Daters, you’ve gotten too comfortable. It’s time to position yourselves as brave explorers.

Dating, like any other type of social interaction with an agenda, is something that requires some extra oomph. And the first date? That’s usually the hardest push, dragging you out of inertia.

It is not easy to take time out of your precious life to brave the unknown sea of singles and face the tough headwinds of your own stubborn patterns. It is not convenient to work on secure communication, boundaries, self-growth and attachment issues while staying true to your core values. No part of acquiring dating skills is just an item you can order overnight from Amazon because you forgot to get it at the store today.

Dating is not always comfortable and reliable. It is not something that knocks on your front door and begs to be let in when you’re working from home and never socialize outside your friend circle.

Dating can be daunting, and it takes real courage — courage to get started, courage to start again, and courage to keep going, even when there are setbacks.

Courage is taking action despite fear, whether that’s seeking something out, or having your eyes open enough to know when and how to take advantage of a situation when it’s before you. When I think of what courage means to my clients, this is what I see:

Courage might mean:

  1. Finally working on yourself and healing some emotional wounds.
  2. Admitting you don’t have all the answers and need help along the journey.
  3. Trying something new, even if you feel foolish.
  4. Making eye contact or making a first move, even though it’s hard for you.
  5. Saying how you feel, why you need something, or being honest in a tough situation.
  6. Setting boundaries for the first time, or upholding them during a difficult moment.
  7. Saying no, walking away, and picking up the pieces to heal and start again.

Searching for deep emotional connection is a vulnerable act. It takes time and effort in ways that are hard to see results from, and most of us experience some form of rejection in the process, which feeds the fear that destroys our courage.

Courage on the Apps

My clients are usually out of practice with real dating, but don’t always know it. They think they’ve been “dating” on the apps. They haven’t. And when I mention something like speed dating, most of them have a long pause with fear in their eyes. Like… leaving my house and meeting with… other single people?

Courage, I say. Be brave. Have courage.

I find one of the hardest things for people to do on the apps is take a chance on a date when they don’t have all the information and show up to face a real person. My clients feel so safe on the screen, waiting until they feel some sort of certainty before making a real move. Even messaging first is starting to feel like being pushed off the diving board for many folks.

Somehow, that stepping stone from chatting online to sitting two feet from each other has transformed into a Grand Canyon-sized crossing that fewer and fewer people have the guts to trek.

Were we braver in the earlier days of app dating? Were we less scarred by the repeat ghosters? Were we having more fun with it instead of expecting so much? Were there more real profiles? I really don’t know. But it seems the app dating world is lacking some courage.

Online platforms give us the illusion of sitting back with all the control and feeling that something will just come to us if we research long enough. Signing up for an app might feel courageous at first, but if the action dies there, we have a problem.

We are not built for swipe culture. It’s crippling for many, and yet, its addictive nature is hard to rip ourselves away from. We suddenly don’t have the courage to leave the screen!

We can feel very righteous in our ability to say yes or say no as we peruse profiles, and can treat people like an episode of Desperate Housewives — enjoying judgment for a while and when it gets too annoying, just turn it off.

Courage means exploring and getting out there on real dates. I implore you to explore more and get curious with all those “maybes” in a safe, low-pressure situation. No matter how fancy the tech is, you can’t get much from a static profile and I don’t think you ever will. Humans are just too complicated and terribly unreliable narrators of their own lives. We always have to remember we have blind spots and are swayed by our bias heavily when faced with the paradox of choice. Go for the thrill of a surprise!

Trying to predict what people are going to be like from an app is the metaphorical equivalent of sitting in the boat before setting sail and looking at a map from the 1600s agonizing over how much you might like where you end up. It’s not very accurate. General idea? Maybe. Reality? Heck no.

Leave. Your. Screen.

Courage Through Rejection

Courage to brave the unknown is an underrated strength needed in dating because of our abhorrence of romantic rejection.

There is so much fear behind the possibility of emotional pain, shame or embarrassment, all of which swim through our minds as we try and predict what might happen on dates.

With online dating, “rejection” happens in unmanageably large amounts for our emotional health. Simply not matching with people we’re interested in or not getting a message back from a complete stranger hits us as a personal rejection.

I always tell my clients — our emotions aren’t actually set up for the amount of experiences we might have on an app in a day or a week. We experience dozens of flirtations and rejections that magnify feelings of unworthiness and lock us out from courage.

We’re also incredibly sensitive to social rejection because we are programmed to want to be liked (even if we don’t like the other person). What a tough gig!

So, how do you summon the courage to get out there with the possibility of rejection? Well, no one can fully protect you from hurt feelings when a real rejection happens. No one can or should force a “yes”.

But what I remind clients of is that the right partner will want to date you. In fact, that should be one of your top criteria. Someone that likes and appreciates you. Someone that wants to spend the time. Plain and simple.

What you want is someone who enthusiastically wants to date you and is available to do so. What you might perceive as rejection when someone doesn’t match, mysteriously unmatches, or stops messaging is nothing more than a stranger on a screen. You cannot assume anything about them except that they are not available or interested — and that’s enough!

Courage From a Growth Mindset

Yeah, yeah, I’ll have courage when I know more, you might think. I’m plenty brave, I just don’t want to waste my time.

I cannot tell you how hard I wince on the inside when someone uses that phrase with dating. Part of the process is spending time, and what you choose to learn from or reinforce with that time spent is entirely up to you.

If you set sail and end up landing somewhere you’ve been before accidentally, do you stop trying? If you end up in inhospitable territory, do you turn around, stay there make the best of it, or continue on to see if something better is around the corner? If you try again, do you do something new? Do you use a different starting point? Do you change your navigation system?

This is how courage serves dating — it’s the entry point of a growth mindset that tells us we can absolutely do better, achieve more, and learn from our experiences, as long as we believe that our capacity to learn and grow is not finite. It is ever expanding.

A growth mindset offers us a chance to see dating as a personal growth opportunity, where we get to know ourselves and others better, while sharpening our relationship tools.

My clients that are in the dating pool for a while make big gains for themselves in areas like conflict, self-care after setbacks, secure communication around feelings and boundaries, and how their love languages work with others. They also find that these areas of strength benefit them greatly once they get into something serious.

We don’t wait until we have a partner to learn how to communicate (or at least we shouldn’t). We need to be working on all those skills during the dating process and even using those things as a way to understand if something is working or not. How’s that for getting some courage to practice?! You’ll have a rock solid foundation to build upon!

Change the way you date. Get a coach. Get dating.

Liking the vibe? Interested in more dating tips? Looking for a dating coach? Follow @YouCanDateBetter on your social channels and check out our site at You Can Date Better where you can sign up for our newsletter.



You Can Date Better

Writing/content curation by Carrie Prince, founder & boss lady behind — coaching & consulting for the current online dating landscape.