There is enormous value in us continuing to face moments of difficulty, over and over again in our lives. Having to deal with rude messages from a man on a dating app or disappointment about ghosting aren't just important because they're necessary steps toward what we're looking or (“you have to kiss a lot of frogs until you find your prince”).

The uncertainty, which can come with disappointments like ghosting or a “meh” date, is a sign that we're putting ourselves in a situation with the potential for upside. But if we charge our dating life with too much unknown (betting big to win big, looking for our person), it's like we're day trading - not likely to succeed in the long run! 

Many times in conversations with clients, I will hear, “But how am I supposed to be sure that he's right for me?” This is usually in reference to a guy that they've gone on a few dates with and things are starting to look like they're moving in a good direction. 

If there's one thing I've learned since becoming a coach - what themes I start to notice in my clients or even in the comments I get on my most recent TikTok always seem to the things that everybody (and especially I) need to hear myself. 

When something bad happens - you get ghosted, dumped, fired, rejected, ignored, forgotten - the feelings are painful. It's normal to reckon with, “how did this happen? why did this happen?” and then the follow up I hear most from clients or in the comments of videos on TikToks (whether explicitly or more subtly): “what did I do to cause this?” or in other words, “is this my fault?”

I know you have something in your life that you're suppressing right now. Whether it's anger, guilt, fatigue, sadness. There's something in your life, a feeling that when you start to feel that wave hit you, you immediately go to work pushing it away.

When did you learn that you can't be yourself? When did you learn that asking for consistent effort from someone your dating is “too much”? When did you learn that things don't work out for you? Or that the only way to get wealthy is by marrying rich? Or if it's easy to get, it's not worth having?

Are you in an early dating scenario and want to get closer to him/her/them? Are you feeling stuck in your job and feel like there's something more out there for you but you can't get yourself to apply for new things? Are you swiping on the apps and disappointed with what you're seeing?

Dating is hard because it's vulnerable. Our emotions are involved and it's almost inevitable that we get hurt. But avoiding hurt isn't the goal of dating, finding connection is.

What step might you need to take right now that feels risky and scary because you don't know if you'll succeed or get what you want?

Why do we care so much about confidence to begin with? Why is this a concept that matters to so many people? If I had to guess, because we’ve seen over and over again that confident people seem to get better outcomes.

If you want to be confident at work, magnetic in your dating life, secure in your interpersonal relationships, the game is not to look for proof from the princes on the dating apps (lol) because that would be like Cinderella walking into the ball still in rags and asking someone to tell her she looks like a princess. The game is to find all the whispers of the evil stepmothers and stepsisters of your past and show them the door.  

The biggest thing our brain perceives as danger (even if sometimes unfairly)? Change. 

Are you saying to yourself: I'll be so happy once I'm in a relationship, I'll be so proud when I get to lead a project by myself, I'll be so confident when I can afford a better wardrobe, I'll be so calm when I can stop overthinking my texts. If so, you need to read this

When you're in the early stages of dating (we're talking dates 1-5), do you find yourself constantly analyzing the text conversation, thinking in great detail on the right thing to say, how frequently to text, etc.?

I've been thinking a lot about this concept of “earning a break.” I find some weeks I am completely comfortable completing some list of tasks and then giving myself time to rest. Other weeks, sometimes even when I've been objectively more productive, I feel guilty stopping to rest when there's objectively more to do (or so I tell myself).

When we act delusional, when we start to experience the world as we want it to be rather than what it is, we offer ourselves a new experience before the proof is there.

If you pause for a second and really get honest, is there an area of your life where you're being really hard on yourself? Given you ended up here, there's obviously a higher probability that dating is one but are you really hard on yourself about why you aren't already making six figures or why you said that awkward thing at your dinner last night?

If there's one thing you have probably heard over and over again if you are even a tiny bit in the personal development/self-help space, it's some version of “you have to love yourself first” or “what you want will come to you when you feel worthy of it.”  

Dating is not a test to pass. Why does dating seem to be such a kryptonite for the confidence of high-achieving women?