We recently connected with Jesenia Caracciolo-Clayton and have shared our conversation below.

Jesenia , looking forward to hearing all of your stories today. Do you think folks should manage their own social media or hire a professional? What do you do?

I manage my own social media

Jesenia , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

The calendar reminder he’d set for her birthday popped up on his phone, “her birthday is in a month, I’ve got time”. In the blink of an eye, he was staring at his phone at a notification that was telling him that her birthday was in two days. He hadn’t done ANYTHING and didn’t even give it thought. He thought he had plenty of time to put something together but with the presentation due at work and the kid’s sporting events, he had run out of time, and now he had to come up with something good, and fast!

And from this and so many situations like it is how The Date Night was born.

I’m Jesenia and for the majority of my adult life, I had been in Corporate America working as a Project Manager in the Contingent Labor space going about life climbing that corporate ladder. 15 years had come and gone and while I was comfortable, making a good living and acquiring new skills every day, I wasn’t fulfilled. I was very good a what I did but what was the drive? What was my purpose? In 2018, I gave birth to my 3rd child and immediately after ended up unexpectedly pregnant with my 4th. My then husband and I had just opened our brick-and-mortar flooring store 1 week before we found out we were expecting again. Once we got over the initial shock, we took it all in stride and kept it moving until I went into labor at 25 weeks. I’d go on to spend the greater part of 2019 in the hospital NICU with my son, who was released home in December 2019 which gave us 3 solid months of “freedom” before the COVID lockdowns. Such intimate time to yourself gives you the opportunity and space to do some thinking, a lot of it. I had been the “go-to” for my friends and family for their date nights, anniversary plans, and birthday dinners for the last 15 years but It wasn’t until COVID struck that I recognized the problem- people were busy and convenience was in high demand. Apply that to planning dates and you have a solution that I don’t think a lot of people knew they needed; until we tell them about us.

The Date Night provides convenience and removes the hassle and logistics of planning elaborate dates but creating a done-for-you experience. We offer custom dates that we cater to you and your partner or pre-curated experiences that you can select from when you’re looking for a good date idea in a pinch.

We are pioneering this idea of a full-service date concierge service and we are full of so much energy and excitement for what the future holds for The Date Night. All of our dates are planned by Orlando locals and experts on the latest and most exclusive places and happenings in Central Florida. We have a weekly newsletter (sign up at thedatenightorlando.com) that delivers weekly events, concerts, shows, and festivals right to your inbox along with restaurant recommendations and what’s newly opened or coming soon to Orlando. We also post a monthly blog with events all around Central Florida for that month.

My team is made up of Florida natives who have a deep seeded love for the City of Orlando and want to share the magic of this city through each curated experience.

Have you ever had to pivot?

In 2018 I was working full time in my corporate career of 15 years. I had just given birth to my 3rd child and my then-husband was opening up a brick-and-mortar flooring store in our city. Oh, it gets better. In order to support him and his dream of business ownership, I leave my career to work in the store full time with my infant daughter in tow. One week after we open the doors we find out we are unexpectedly expecting and at 25 weeks pregnant, I go into labor with my 4th child.

I spent most of 2019 in the hospital with my son and most of 2019 at home due to COVID. During this time, life illustrated some pretty clear points:

1. The trajectory of your entire life can change in a split second – learn to be adaptable
2. The world around us is changing at an unprecedented pace – learn to be creative
3. Health is #1 – without that you’ve got nothing else – learn to care for your WHOLE body (mind, body and soul)

In 2020, we had to sit down and make some quick assessments of the current status of the world and adapt quickly and creatively to ensure the success of our business. We did and by 2022 we were named “Best in South Lake [County]”.
Also in 2020 I had a huge wake-up call. With everything that I had just gone through in the prior years with my son’s health, I knew that I needed to focus on what inspired me and lit me up inside rather than doing a job simply for the security of a paycheck. From 2019-2020 I used any time that I could get to myself to find a way to use my strengths in a way that would light me up inside. I had been the “go-to planner for dates, anniversaries, and events for family and friends for over 15 years when in 2020 I recognized that there was a problem to solve for couples looking for date experiences that coincided with something I had been doing for the greater part of my adult life that I really loved. The rest is history.

How did you build your audience on social media?

When it came to social media I knew that this was something I wanted to manage in order to connect with my audience and potential customers. I want to be the face of my company and create a connection that shows that there are real people behind the brand.

In building my audience on social media my biggest piece of advice would be consistency. Show up every day and let people in to see what you’re doing. Even if it isn’t the most perfect or polished content, your audience is there to see you. They want to hear how you can solve their problems and how you can make their lives better with your solution. Tap into the emotion behind their problems and how they’ll feel once you solve them, Honestly, don’t put too much pressure on yourself – they can smell the fear. Just be authentic and connect regularly and the growth will come.

Contact Info:

• Website: https://www.thedatenightorlando.com/
• Instagram: https://www.instagram.com/thedatenightorlando/
• Facebook: https://www.facebook.com/thedatenightorlando
• Linkedin: https://www.linkedin.com/company/84000598/admin/
• Twitter: https://twitter.com/TheDateNight1
• Other: https://www.tiktok.com/@thedatenightorlando