in: dating + single

Riding on to Romance: The Road Trip Date

Guest Contributor

Why hit the a coffee shop when you can hit the road? The road trip date may not have been your first idea, but here are some excellent reasons it should.


Here’s a paradigmatically ‘50s image: a cute couple gliding down the road in a shiny red sports car. Rolling green hills can be seen all around them as the wind gently whips their hair about. The idea of the road trip date is one as old as the automobile and romance in the countryside predates even that. Yet, in this era of modern speed dating and the rush to plow through potential partners’ profiles as quickly as possible, looking for that one magic match, we’re starting to lose touch with our dating past.

There’s no doubt that some old courtship traditions are best left in ancient history, but the road trip date is definitely not one of them. Here’s everything that you need to know to have a killer road trip date of your own.

Prepping a Road Trip

A question that comes before any date is “where do we go?” One great thing about a road trip date is that you can go just about anywhere. The only limits on where you can go are the roads and your patience in the car (or your interest in your date). Don’t be afraid to get in the car and just start driving.

For example, I didn’t know until a few years ago that not 30 minutes out of my city there was this great little campground settled in the sandy banks of a small river.

Here’s a road trip date: get in the car without knowing where you’re going, discover this charming little campground, and break out the food for an impromptu picnic.

If you want something a little more predictable, you can always try some classic road trips. Tried and true routes are going to be full of interesting destinations and tons of great romantic opportunities. Be sure to pick your route with a mind for how long you’ve been dating. Eight hours in the car with your romantic partner of two years is one thing, but try to keep things a little shorter for third or fourth dates.

What you should bring with you depends a lot on where you think you’ll be going and what you plan on doing there. However, there are definitely some standbys that every road trip date needs.

  • Try to bring something light to eat so you’re ready for action no matter what the date throws at you. Fruit is always great and trail mix is something that can be passed between the two of you while you drive.
  • Bring something to listen to—it could be music, a book on tape, or a few episodes of a good podcast. I would lean towards the latter two unless you and your date have similar tastes in music. Not only are these less likely to spark conflict, they’ll also give you something to talk about in the car and afterwards.
  • The best places to cuddle are always going to be on the couch or in bed, but neither of those are going to fit in your car. With a little creativity you can hang a hammock pretty much anywhere. Plus, the shape of a hammock turns it into an automatic snuggle machine as you and your date will both slide to the center.
  • Keep a mental list of questions to ask your date. A road trip date is no different than any other insofar as it’s an opportunity for you and your date to discover more about each other and get a feel for the match that you two make.

How to Road Trip

There’s no one right way to do a road trip date. In fact, trying to force yourself into one set schedule is probably the only wrong way to do it. One of the great things about a road trip date is its open-endedness.

What you should do is come up with a general route that you and your date want to follow. You can swing by local hotspots, connecting the dots in a “greatest hits” type tour, or just pick a road and say “You know, I’ve always wondered where this goes…” You never know what you might find on a road trip. It’s easy to stumble across new vistas, free food, or even concerts.

Music festivals can make great road trip destinations, planned or otherwise.

For those in-between moments, playing road trip games is a good way to pass the time and a great way to get to know more about your date. What kind of words do they gravitate towards in Mad Libs? Would they rather spend the evening inside reading or out on the town?

The Magic of Road Trips

In the end what makes a road trip date so special is that it’s just you and your partner against the open road. Not only is it a great bonding experience, but it’s also a great chance to learn more about yourself. After all, we don’t grow as people in a vacuum; it’s only when we’re challenged by the people around us and the situations that we find ourselves in that we the truth about ourselves and each other.


About the Author

Nick CesareNick Cesare is a freelance writer and violist. After a long break he is getting back into the dating world along with all its mysteries and joys.

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