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.

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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.