In Dating, Are You Stepping Up to Bat?

This is an excerpt from my book Show Up: Finding Love for Independent Women. Now available on Amazon!

After doing personal growth for a few years and feeling frustrated with my dating life, I wondered if things would ever change. Then I met a guy named Greyson. 


Greyson and I went back and forth liking each other for years and had this cute, stupid dynamic where every time we were around each other, we’d both become really shy.

We always hung out as friends, and eventually I developed a huge crush on him, though I didn’t want to say anything for fear of rejection. Also, in my head I always thought it would be more romantic if the guy made the first move. Not true!

Finally one night I picked up the phone and called him. Not gonna lie, it was awkward as fuck because I wasn’t used to talking like this, but I knew letting things organically happen between us wasn’t working. We had literally tip-toed around each other for years.

It was night time and we had just finished hanging out at a bar with mutual friends. I started to drive home and hated that I just hugged him bye like we were friends. 

I pulled over because it was a now or never moment. I got my phone out to call him.

“Hey!” I said awkwardly.

Hey…” he said with a confused tone.

I don’t remember fully what I said but it was along the lines of “I like you and would like to hang out as more than just friends. Can we do that?”

I must have said it with my eyes closed tight, barely able to breathe. Good god. He’s going to reject me solely based on how awkward I said it, I thought.

Do you know what he said?

“CC, I can’t believe you are telling me this because I’ve liked you for so long and I didn’t think you liked me back in that way. Yes I’d love to.”

Logic here. Ding dong! If I can’t tell or show someone I like them, I’m not even giving them a chance. This was the part of me that was scared to be vulnerable.

Could he have said no? Of course. In which case I would have been super bummed, but at least I went up to bat. If it was a no, it would free up space for me to move on.

He was very cute and sweet, and right for me in that moment of my life. I learned a lot about myself during this time because he and I were so emotionally similar that it kind of felt like I was dating…myself.

Huh, so that’s what I’m like.

I’m happy we dated, even though he did crush my heart into a million pieces at the time we broke up. He didn’t want to take things further when I did, but he was (and still is!) a good person. We weren’t on the same page, and after mourning it, I came to accept that.

Are you taking risks and putting yourself out there? Are you showing up, even when it means being vulnerable? Don’t close yourself off to possibility because you’re afraid to act.

2 thoughts on “In Dating, Are You Stepping Up to Bat?”

  1. Life is so simple. We make things complicated. Just close your eyes and take a deep breath. Feel the power flowing into your soul. This power is yours and it can make you so strong that you can’t imagine. Feel the serenity that touches your being and choose the next move. As in chess. So simple.

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