October 12, 2020: You Gotta Kiss A Lot of Frogs... or Not
- Courtney Gaylord
- Oct 12, 2020
- 8 min read
Updated: Oct 12, 2020

Hi, Friends.
As I am writing this out, I am sipping on my Welches sparking Rosé in my fancy Tiffanys wine glass with old T-Swift in the background. I am really wishing my glass was actually filled with a delicious glass of red because of the vulnerability in this blog post today. I feel like I am opening up my diary to the world. Even though this may be a little unnerving, I am hopeful that it can shine some light on what could possibly be a tough time in your beautiful life.
Today, I hope this post reaches all of you as always, but especially the younger crowd. You know, the kids that are starting to figure it all out. To my loves that are dealing with their first heartbreak, the feeling of being lost in uncharted territory, or the pain of what you thought your future would look like being ripped out from underneath you, I have been there. This one's for you.
"You Gotta Kiss A Lot Of Frogs"
So, now that I am officially expecting our first little girl, I have thought about this over and over and often gone to my mom for advice. I have asked her so many times if she could go back in time and not let me date in high school, would she? She always says the same thing,
"Court, first of all, there was NO telling you 'No' when it came to staying away from boys. (shocker..) Second, you needed to figure it all out on your own. It was important."
While I totally agreed with my mama, thinking about my future daughter having her precious baby heart broken in high school (or at all) brings immediate tears to my eyes and sickness to my stomach. Even though I know some couples get super lucky and their high school sweetheart ends up being their "Prince Charming", let's be honest, these relationships usually end in heartbreak. If you have gone through this kind of breakup in your life, you know that high school heartbreak is ROUGH. To quote Sheryl Crowe, "The first cut is the deepest." If you know, you know.
If you are reading this and you are currently experiencing this heartbreak, please know that you are NOT alone. Everyone, and I mean, EVERYONE hates it when people say, "There are other fish in the sea." So, I am not going to say that. All I am going to say is that I know that it sucks and that it hurts more than you ever thought humanly possible. You're not sure how you can handle the loss of not only a boyfriend or girlfriend, but also a best friend. I get it. I am actually getting a little teary right now thinking back to that time in my life and thinking back to that pain and that you have to feel it, too. But please continue to read on and know that you have SO many things headed your way. So many. You won't even believe it!
This leads me to my second point about these first relationships. They are life changing in the way that they help you learn SO many things about yourself and how to navigate through future relationships. (Yes, believe me, precious one, there will be future relationships) You learn how you like to be treated and how you don't like to be treated. Before you know it, you're in college and if you're anything like me, you are terrified, but EXCITED about all of the people (AKA, boys) you will meet.
My issue in this next phase of my life (college) was that I was always looking for "THE ONE". This isn't always a bad thing, but to quote my brother, "They can't all be 'THE ONE', Court." The bad thing about this mindset is that believe it or not, most college boys aren't looking for "The One", unfortunately. This mindset would cause me to fall too fast and trust too quickly which then led to more heartbreaks. Over and over again, actually. I would even go back to that high school sweetheart thinking maybe he was actually "it". Nope. I kept trying to make that one work, but in the end, he was just meant to be part of a special time in my life.
I wish that I could say that was the end of my streak of heartbreaks, but it wasn't. As I was ending my college career, a friend from a former college I went to resurfaced. Loves, this was one of my more serious "frogs". I was recently 21 and could have SWORN this frog was going to turn into my final "Prince Charming", but low and behold, a year and a half later, it just wasn't going to work out. We decided to call it quits. Is that ok? YES. Does that mean he was bad? Absolutely not. Our stars just weren't aligned. If you are going through this break up, the one that would have made your plans come true, I promise you, your time WILL come. You will cry it out and move on to the next frog because you have now learned even more about yourself and what you want for your future.
Flash forward to my to mid twenties and I was still single. My plans of getting married at 23 and kids at 25 were quickly becoming a distant dream. Guess what, that "plan" I had when I was 15 hardly works out for anyone anyways. I needed time to GROW and learn to be who I was without ANYONE else. Not everyone gets this special time alone, but I did and I wouldn't trade it for ANYTHING. I had my own place, started teaching, and started dating on my own terms.
Did I still have some heartbreak? Yes. There was another time when I thought I found my "Prince Charming" (actually another former frog) yet again, but the timing just wasn't right. My dreams with that frog didn't come to fruition and that's okay. It turns out, you can give yourself heartbreak, too. That special frog and I stayed friends and for that I am forever grateful. After him, I continued to date other froggies, but nothing serious came along and that was okay! I focused on being the best ME I could be. I ran my first half marathon with my sister and just loved living my life for ME!
Looking back to these times in my life, I ask myself..
Was there growth? YES.
Did it take time to understand my worth? ABSOLUTELY.
Did I make mistakes along the way? You bet. Who didn't?!
Even though there was hurt, loss, and mistakes, I would not trade ANY of these stops along my journey because it actually did lead me to "the one". My very own true "Prince Charming".
William Christopher Gaylord. He was the one I didn't see coming. Seriously. After every break up, my sister would always say “That guy was pretty sweet, but I can’t WAIT to see how great the one you end up with will be” and boy was she right. I was no longer looking for "THE ONE" when Will stumbled into my life. I was still casually meeting people and deciding as an adult, what I saw was compatible for my future and what wasn't. With Will, it was steady. He called when he said he would call and he showed up when he said he would show up. He was sweet. He was kind. He LISTENED. He was interested in me and my life. With him, I always felt loved and wanted. I felt cared for. I felt beautiful. I felt unstoppable. It was and still is just an easy love with him. Don't get me wrong, we have an adventurous life together, but it doesn't always have to be adventurous. In fact, my favorite moments together are just relaxing watching tv or playing a game. After we shared our first "I love you's" about 6 months in, we never looked back. There were things that could have torn us apart. After dating for 8 months, he had to move 5 hours away for his residency program. What could have been a deal breaker, just wasn't. I didn't care if it was halfway across the country, we would make it work. After one year of long distance, I moved away from everything I knew to be with him. Nothing could stop me from making this dream come true. I thank God for him and everything I learned along the way every single day.
You see, every love (or frog) in your life has a purpose. They all teach you things and help you grow into a mature human being. I am so grateful for each of my frogs in my life. I truly think that I was blessed with them. I still think of them fondly and don't hold any negative feelings whatsoever. You know why? Because they led me to Will. Just like they led me to the love of my life, I like to think I helped them as well. I will always be cheering them on. I love seeing them so happy with their now babies, wives, fiancés, and perfectly wonderful lives. This is proof that no matter what your heartbreak feels like now, it will be worth it in the end.
So, as you can see, you may have to kiss a couple frogs (or 20) but please believe me when I say, don't give up -- it will all be worth it one day. Your prince is out there. He is just molding himself into who you need him to be, too.

Or Not
What's all this talk about relationships and love?! Did you know that your "Prince Charming" might not be a man, girl, or human being at all?! It could be your job, starting a family by adopting a child by yourself, being perfectly happy with living your life without a spouse, becoming a priest or a nun, or any other purpose you have for YOUR life.
My journey to finding my "Prince Charming" just happened to be full of boys leading me to my dream man, but that absolutely doesn't have to be the case for you. The last thing you should ever do is fill your life with "frogs" that someone else thinks you should have.
Maybe your frogs are different life choices you make to find what you really are called to be and do.
Maybe an ex husband or wife ended up being a frog along the way to finding what or who your Prince Charming really is.
Maybe you have had failed attempts with many frogs just to find out that you are much happier with your life when all you have to worry about is yourself.
The moral of this part of the post is that your story doesn't have to end up like mine because we are NOT the same people. We have different lives and different ambitions.
Focus on what you want out of your life and who or what your specific "Prince Charming" is. Then, GO FOR IT.
Thank you for listening to my story. I hope you can take away something from the post and use it in your life. If you know someone who needs to know that they are not alone in their heartbreak, no matter what it might be, please share this message.
I love you all so stinking much!
XOXO Court
I was just telling a mama of a teenager that it’s okay to be sad, too, as the mom! You get to know the boys like they were your own, too! I love you, mama! Thanks for always being there.
Courtney, I loved your post today for two reasons. First, it brought back so many emotional memories as I went through all these breakups with you, and second, you are totally right to refer to a person's frog as just a step along the way to finding your perfect job, lifestyle, or individual happiness in whatever it may be. That is a great point for young girls trying to find their own identity and happiness.