How to Date Yourself : Solo Trip In Charleston

How to Date Yourself

Dating yourself can be a hard concept for some, however it is necessary to really discover who you are and what you want in your life.

This is how I dated myself, and discovered some amazing things along the way.

First, pick a location that will inspire you. I chose Charleston, and there so many things to do there when you are on a solo trip. 

This has been a season in my life where I have had to learn how to treat myself/ date myself the way I would want to be treated/dated. Like Iyanla Vanzant always says –“Child you have to do your own work!” I am doing my work, and enjoying the process.

Solo Trip to Charleston

After coming out of a relationship that I thought would be my last, it is hard to face the fact that I have to start from square one. But, the great part about it is that I now know what it is I need to do to get in that space where I am open to receiving the type of love I want and deserve.

First, I have to deal with my own insecurities. I had to have that ugly cry, ask God why a couple of times, and then begin to pay attention to the messages He was delivering to me that I wasn’t paying attention to, and begin to live life the way it was meant to be.

I realized that I couldn’t force what I knew He had for me, and I couldn’t go looking for it either. I had to get busy in the fields like Ruth. I had to live life… I had to be Kyla and be comfortable being Kyla… by herself in her own lane… doing what I love to do. So, I decided that I was going to go the Charleston for a solo trip and do whatever it is I wanted to do –shop, eat, job, take pictures, or just plan sleep in! I thought it would be a little awkward, but it turned out to be an amazing time!

The Perfect Place

Charleston is a familiar place for me. I used to go there when I was a child growing up in Atlanta, but never as an adult. It’s a laid back town with great food, culture, and shopping. A great place to have my first solo trip.

The Perfect Hotel

The historical Kings Courtyard Inn

I knew I had to stay somewhere that spoke to my soul, and I booked an amazing room that was just perfect for me… Kings Courtyard Inn, a historical hotel, located right on the strip with all the action and shopping. It has so much personality and it just made me light up a little on the inside. It was the perfect for an “Eat, Pray, Love” kind of adventure — free breakfast in bed, garden seating areas, and peace.

Find The Perfect Outing

The great thing about dating yourself, is that you don’t have to weigh in another person’s opinion. You can truly do the things you want to do without feeling like you are dragging someone along unwillingly. It is important to find an activity that is a bucket list for yourself. Big or small, planned or spontaneous — find something that will give your heart joy.

Mines was stopping by the Carolina Polo & Carriage Company in Charleston, South Carolina.

Carolina Polo & Carriage Co.

I was there for two days and one night, and I made sure to make the most of it. I indulged in ice cream on a stroll through the city, visited the local shops, went for a nightly jog, and caught a carriage ride around the town.

How to Date Yourself

I have learned a few things through this experience.

1. Pick a place that you know you would really enjoy. Be honest with yourself about what you like — If you like history go somewhere historical, if the spa is your thing go somewhere peaceful, etc.
2. Keep an open mind! Traveling by yourself is a little different then traveling with others, but it’s not bad. Once you realize no one knows you are by yourself, you will be just fine.
3. Try Something New. It could be a new restaurant or an activity. For the first time, I jogged while on vacation at sunset. It was so peaceful, and I am happy that I was able to have that moment with myself.
4. Stay Safe. Let someone you care about know where you are going especially if you are a female. I did my FaceTime check-ins with my family (mainly to show them what they were missing).
5. Take Lots of Pictures. You are going to want to remember this journey. Get a selfie stick or ask someone to snap a quick pic of you along the way. Safety is always key! I would usually ask a couple or two ladies trying to take pictures if they would like a picture together and most times they are happy to return the favor.
6. Work Your Way Up to a Trip. If going on a solo trip still sounds a little difficult, try taking yourself out for a day, a quick movie, or spa visit first. Get use to you in your current surroundings first and ease into a trip. There is nothing wrong with taking baby steps.

This experience was the start of me Affirming the Life I wanted for myself. If you are looking for ways to intentionally live the life you want for yourself, the Affirming the Life You Want Checklist is a great place to start!