Road Trip for the Holidays

Have you heard?  I’m going on a two-week road trip for Christmas with my boyfriend, Mike.  This is a far cry from the traditional Christmas, but it will be an adventure to say the least!  Traveling from central Texas to explore Louisiana along the Mississippi onto New Orleans and finally making our way to the tropical Florida coast line – this will be a holiday to remember.

I will admit the idea of spending the holidays on the road was something I had to get my head wrapped around at first.  Usually the holiday season is spent running from one Christmas party to the next, overeating a big Christmas day meal my mother had spent all day making and then of course eating leftovers for days.  But it in the spirit of keeping an open mind and trying new things, I was ready to shake things up a bit and go on this epic holiday couple’s road trip with Mike.

Although this will be an awesome way to spend the holidays together, the thought has crossed my mind – “how will we keep the holiday traditions alive on the road?”

My first thoughts were create a fun holiday play list, find a travel size Christmas tree, decorate the car with battery powered festive Christmas lights, but then I realized it’s not about the stuff.  It’s really about the person you are with and the experience of driving across country and making memories with the person or people you love.

Here are the top 5 ways Mike and I are keeping the Holiday tradition alive and creating our own traditions during our epic holiday couple’s road trip:

  1. Immerse ourselves in a culture outside of ourselves.  We will be completely open to driving down a road we have never traveled before, talking to locals about their city and making new friends along the way on our road trip.  Experiencing a holiday tradition different from our own, Bonfires on the Levee in Louisiana will kick off this goal of experiencing a new culture.
  2. Create new memories and a new tradition.  As I said this will be Mike and I’s longest road trip together and our first Christmas … that’s a lot of pressure, but going with the flow and starting our own tradition, as a new couple, will make our relationship stronger.
  3. Keep our friends and family engaged on the road.  I want to take everyone on this trip and show how traveling can open your mind and can heal your soul.  So in addition to the new norm of social media, Mike and I will be sending a post card to family members and friends at every city.  Sure we may arrive back home before anyone gets their post cards, but seriously who doesn’t like getting snail mail! (note to self…pack stamps)
  4. Tell stories.  Similar to our first road trip, reminiscing of our favorite childhood memories, Mike and I will share our favorite holiday stories.  And hey maybe one day we will be able to tell our children about the time we spent our first Christmas together.
  5. Ok ok…I’m still buying the little travel Christmas tree… but don’t tell Mike.

So, we’re hitting the road!  And we want you to follow along as Mike and I tell our Holiday travel story this December.  Some of the highlights you can look forward to are:

  • A tour and night spent at Oak Alley Plantation on the Mississippi
  • The lighting of the Bonfires on the Levee
  • A jazzy New Orleans Christmas Day
  • Ringing in the New Year on the tropical beaches of Key West

Have you ever spent the holidays on a road trip?  If so, how did you keep holiday traditions alive?  Leave me a comment, I want to hear from you!

Happy and Safe Travels, xx Jennifer

How to Go on a Road Trip Date

Leaving Texas on a plane at 5 am to go on a date in California was something that was out of my comfort zone,  my friends and family thought I was crazy – but I had decided that it was a risk I needed to take to see if this new relationship with Mike was going to work out.


I landed in Ontario, California and walked off the plane filled with excitement, hope and a stomach filled with nerves.  In my head it played out a lot like a romantic scene from every love story, as the girl runs and jumps into the arms of her lover and then they run off into the sunset happily ever after.  Let me tell you, if every relationship began that way the world would be a better place.  But it didn’t start like that – It started with both of us coming into a new relationship with some hesitation and proceeding with caution.  After all we were still getting to know each other and a California road trip was just the thing we both needed to get to know each other better.

This wasn’t just any date, it was a California road trip date, that Mike had mapped out for us.  We drove from Ontario to Santa Barbara, to the charming Danish city of Solvang and finally on to Ojai in less than 72 hours.  Knowing that we had a four hour car ride ahead of us until we made our first stop in Santa Barbara, I wanted to come up with a creative way for us to get to know each other better because I wasn’t about to let awkward silence ruin our couples road trip.

I turned to my friends as I often do for advice and direction on every aspect of my life, so naturally I got them involved on this road trip. I created a “Cali Party Line” group text… a modern day party line.  The group text was a fun way to share information, crazy gifs and the best part… what questions should I ask Mike to get to know him?  This opened the door for a so many questions that I never would have even thought to ask.

On the road trip as I started to ask Mike some of the questions my friends put together it helped keep the conversation flowing and often we found ourselves telling stories based on the answers to each question.  It definitely filled four plus hours of drive time and the best part, it allowed us to get to know each other better and inspired additional questions.

Planning a road trip date?  Hopefully I’ve inspired you to get outside of your comfort zone and on the road to building a new relationship.  Below I’ve recapped over 20 questions that my friends put together for Mike and I during our road trip around California.  Happy dating! xx Jennifer

  1. What was your favorite Halloween costume?
  2. If you were on death row, what would be your last meal?
  3. Do you like dogs?
  4. What’s your best travel story?
  5. What’s your most irrational fear?
  6. What’s your go to Karaoke song?
  7. What are your pet peeves?
  8. Do you have an unusual talent?
  9. What are you legit bad at?
  10. What’s the worst fad you ever participated in?
  11. Do you have any family traditions?
  12. What was your favorite birthday party as a kid?
  13. Are you more of a Betty or Veronica kind of guy?
  14. If you could have dinner with 3 celebrities dead or alive, who would they be?
  15. Have you ever questions (… sky dived, snow skied, zip lined, etc.)
  16. Where do you see yourself in the next 1, 5, 10 years…?
  17. What is your favorite childhood memory?
  18. What is on your traveling bucket list?
  19. What’s your favorite type of food?
  20. Do you have a favorite restaurant?
  21. If you were married, what are your thoughts on your wife working, or staying home with the children?
  22. What are your financial goals? (note: only ask this question if you feel like the other person is open to having this discussion, asking too early could be off putting)
  23. Tell me more about your extended family.

Curious about how I met Mike?  I recapped our first date and how I knew he was the one, read our love story by clicking HERE.

A Leap of Faith

I bought a plane ticket to California less than a week from takeoff, and I took a leap of faith.  My friends and family were surprised  – and maybe even a little concerned.  I’m not an impulsive person, as you get to know me you’ll find that I typically take a long time to make decisions because I have to first analyze every outcome so I can be prepared.  I am a planner, I don’t like to be caught off guard.  I have always planned my life to the minute and when things didn’t turn out like I had planned I had to make a change – and it all started with a plane ticket to California.

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Santa Barbara, California

Flash back to a month earlier, frustrated with the dating world and determined I would never meet the person God had made for me, I did what most young – single females in their mid-thirties are doing today, I jumped online.  Downloading the latest greatest apps and paying for a online dating platform, I had my bases covered and I started the online dating adventure.

Following what seemed like a really sad country song and a long line of meeting men I hoped would just drop off the planet, it was when I met Mike that my world completely changed.  In the sea of swiping left and right and the conversations that didn’t move past “Hey”, I came across a profile that made me stop and go “wow.”  Mike’s pictures told a story about him, I knew him before we even started a conversation.  I knew he had a soul for adventure, I knew he was kind, I knew that he was different.  I just knew.

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We matched – that’s an online dating term for we both swiped to the right.  So the story begins, a Texas girl meets a guy from Cali.  Out of my element and trying to stay the course of my new found passion for trying new things.

Talking for only a few weeks we decided to meet in person, you know to make sure we were actually real people.  We both had plans to be in the same state and even the same city, so why not meet up?  Making the drive to Austin I decided to call my best friend to talk to me all the way there – you know the best friend who isn’t afraid of anything and always encourages you to just go for it – yeah I called her.

Feeling confident after hanging up with my bestie, I walked into the room, potentially over confident, and I saw him.  I almost stopped breathing but hopefully he couldn’t tell that I was about to go into cardiac arrest.  A quick hello hug and off we went on our first date.

Listen up ladies – Mike made all of the plans for our first date.  He was creative and asked me two questions “are you more of a sit by the lake kind of girl? Or go out on the town kind of girl?”  I quickly answered lake because I could sit by a lake for days and never get tired of the view.  He grabbed my hand and took me to the Contemporary Museum, we sat for drinks afterwards at the Aloft Hotel rooftop bar, then made our way to the lake for dinner.

We then ended the first date with espresso and chocolate lava cake.

On the drive home, fully caffeinated and on a high from what seemed like the perfect date.  Again, I just knew…. I knew I needed to see him again.  I knew I needed to see where this was going to go.  So the second and third dates happened which were equally wonderful if not better than the first.

Mike was back in California and I was back to my normal routine of life when he invited me out to visit him.  Mind you we had only been on a handful of dates so I had to make a decision.  Flashing back to the men that should fall of the planet I thought to myself… what’s the worst that could happen?  If he turns out to be crazy, I can get an Uber and go back to the airport…. I can get an Uber and go to a hotel?


Less than a week out, I pulled up my American Airlines app and bought a plane ticket.  Yep it was that simple.  Breaking the news to my parents, besties and circle of friends was not as simple for the obvious reasons, but I did it anyway and I don’t regret any of it.

Everyday is an adventure with Mike, just like the photos I saw before we even spoke.  Everyday presents a new experience and as we plan for the future together it brings me to life, a life that I never knew was possible until now.