Tips for Going on a Trip with Someone You Just Started Dating
Tips for Going on a Trip with Someone You Just Started Dating
(Without Losing Your Mind or the Spark)
So… you’ve been seeing someone new, and things are going well. Like, flirty-texts-all-day, shared-dessert-level well. And now one of you floated the idea:
“What if we took a trip together?”
Cue the excitement... and also maybe a little panic.
Because let’s be honest—traveling together is a whole new level of closeness. You’ll see each other tired, stressed, off-schedule, and possibly hangry. But you’ll also get the chance to create shared memories, laugh over ridiculous detours, and maybe even figure out if this connection has long-term legs.
1. Talk About Travel Styles Before You Go
This doesn’t have to be a full-on logistics meeting, but a quick conversation about how each of you likes to travel goes a long way.
Some things to gently explore:
Are you more of a loose, go-with-the-flow traveler or a “color-coded itinerary” person?
Do you love doing All The Things or are you more of a nap-by-the-pool type?
Do you need downtime to recharge?
What’s your budget comfort zone?
This convo can actually be kind of cute. Just stay open and honest. You’re not judging—you’re getting to know each other better.
2. Keep It Short and Sweet
If it’s your first trip together, aim for a weekend or 2–3 days max. Think: cozy cabin, nearby city, beach day, cute Airbnb in a walkable area.
Why short?
It lowers the pressure
It’s easier to manage if things feel off
It keeps the energy fun and light
You’re not stuck if you realize your vacation rhythms don’t match (yet)
Let this be a “test trip,” not a honeymoon.
3. Make Space for Alone Time (Even If You’re Sharing a Room)
When you’re still getting to know each other, 24/7 togetherness can be… a lot. It’s okay to take little breaks—even if you're in the same hotel room.
Some low-key ways to build in space:
Bring headphones for solo podcast time
Take a morning walk alone
Offer to go grab the coffee while they sleep in
Agree on some chill “scroll time” or rest before dinner
Introvert or not, mental and emotional space helps keep the vibe fresh.
4. Expect a Moment (or Two) of Tension
Yes, even if you’re really into each other. Traveling is fun—but it’s also full of little curveballs. Delays, bad weather, weird Airbnbs, or just being a little overtired can bring stuff up.
If tension happens:
Take a breath
Assume good intent
Say something like, “I think we’re both a little out of rhythm. Let’s reset.”
It’s okay to have a small disagreement. What matters more is how you handle it—and whether you can laugh about it later.
5. Decide on Money Stuff Ahead of Time
Money can be awkward in early dating, so it helps to talk about how things will be split—before the bill hits the table.
Try:
“Want to split everything 50/50?”
“I’ll cover gas if you grab dinner?”
“Let’s each handle our own activities and snacks, cool?”
No need to overcomplicate it—just make sure no one’s left guessing or feeling resentful.
6. Keep Your Expectations Grounded
It might be magical. It might be a little bumpy. It might be both. Try to stay out of all-or-nothing thinking.
A trip doesn’t need to be “perfect” to be meaningful.
Instead of asking, “Is this person The One?” try asking:
“How do we navigate things together?”
“Do we laugh easily together?”
“Do I like how I feel around them—on the good days and the messy ones?”
7. Let It Be Fun
Seriously. This is the whole point.
You don’t need to analyze everything. You don’t need to make it a relationship milestone. You’re allowed to simply enjoy the hotel snacks, hold hands while sightseeing, and share goofy inside jokes over gas station snacks.
Let this be what it is: an adventure.
8. Pack for Comfort, Not Just Cute
Okay, yes—maybe you want to impress a little. But also? You’re going to be in a car, on a plane, walking around, and maybe lounging in bed watching bad hotel TV. Prioritize comfort. Bring what makes you feel like you.
Don’t forget:
Your favorite cozy hoodie or soft tee
Shoes that won’t destroy your feet after 20 minutes
Noise-canceling headphones or a sleep mask (trust)
A book, podcast, or playlist you can zone out with if you need solo vibes
If you’re comfy, you’ll be more relaxed—and that’s way hotter than trying to hold your jeans together after a long brunch.
9. Let the Weird Moments Be Part of the Story
Something will go wrong. The restaurant will be closed. Someone will snore. Your phone will die at the exact wrong time. That’s just part of it.
The trick is to treat those moments like the memory-makers they are.
Instead of, “Ugh, that ruined the night,” try, “Okay, that was hilarious. Want to make a new plan?”
It’s not about perfection. It’s about seeing how you two roll with life together. Sometimes the inside jokes from a weird Airbnb or a wrong turn are what you’ll laugh about for years.
10. Pay Attention to How You Feel—Not Just How It Looks
Maybe the photos are great. The trip sounds dreamy on paper. But here’s the real question: How do you feel when you’re around them?
Do you feel safe? Seen? Respected? Comfortable being a little messy or tired or real?
Or are you performing a version of closeness that doesn’t quite feel like you?
The trip isn’t a test—but it’s a chance to notice:
Do we communicate well when things are off schedule?
Is there room for both of us in this connection?
Do I like who I am when I’m with them in close quarters?
That tells you more than any sunset selfie ever could.
Final Thoughts: You Learn a Lot When You Travel Together
When you go on a trip with someone new, you see things you wouldn’t notice on date nights alone—how they handle change, how they treat service workers, what their rhythm is like without a schedule.
You also learn more about yourself in relationships—your needs, your flexibility, and your non-negotiables.
So take the trip. Be curious. Pack snacks. Laugh when you miss the exit. And whether it’s your first of many or just a sweet little one-time memory, it’s still worth the experience.
Want more tips on relationships, communication, and nervous system-friendly dating?
At Sagebrush Counseling, I help individuals and couples build connections that feel safe, mutual, and grounded—without the pressure to get everything perfect. If love feels overwhelming or confusing, you don’t have to figure it out alone.
Let’s find your rhythm—one trip, one breath, one honest moment at a time.
