How to Date an Adventurer

On our first date, we crashed a wedding. We were strolling around Lake Merritt after having a couple glasses of wine. As we walked, we spotted a restaurant on the lakefront. A few well-dressed men stood out front and we realized the restaurant was hosting a wedding reception.

“We should crash it,” I joked.
She laughed and her eyes glistened. “Okay!”
“Wait, I was kidding.”
“Let’s crash it!”

She walked intently towards the door, tugging me along, and we stepped into an intimate wedding party happily dancing in a small venue the size of a hole-in-the-wall restaurant.

We passed the welcome table, went straight to the bar, and ordered a couple glasses of wine. I tried to ignore the fact that we were obviously the only Asians in the room.

“Oh shit…I think that’s the bride giving us side-eye.” I said, clenching my wine glass.
“It’s okay! Just finish your glass and we’ll leave.” She grinned.
“Oh shit, she’s talking to the groom. They are both looking over here.” — She continued to sip on her wine.
“EXCUSE me, what are you doing here?” The grooms eyes narrowed.
“Oh…uh…nothing…we’re just…friends with the owner of the venue,” I stammered.
“Okay, well I fucking paid for the venue, so leave.”
“Yeah, sure! No problem. Not a problem. Congrats Pete and Tara! You guys really look happy together.”

We bolted out of there, drunk on wine and adrenaline.


I’m not the kind of person that is naturally inclined to dive off cliffs; I need a little push. Don’t get me wrong — I know these risks are important, make me feel alive, and leave me a better person than I was before, but my heart still leaps up a bit in my throat when I think about the risks. My mind impulsively thinks of the reasons why not to jump.

Jamie first thinks about why we should jump, and that has pushed me into experiences I wouldn’t naturally pursue. Since meeting her, I’ve done so many things for the first time.

  • Finish a Spartan Race
  • Stand-up paddle board
  • Hot Yoga
  • Take a Last minute trip to see the Seahawks play
  • Finish a triathlon
  • Go to a 150 person Vegas trip
  • Shoot a shotgun

Since then, I’ve realized that in her heart, Jamie is an adventurer. It’s not easy dating an adventurer. For those of you that might be dating one, or are considering dating one, I’ve put together a survival guide.


Become a master of planning

  • Adventurers don’t have enough time in a day. Life is full of adventurers and there’s too many things to do in a lifetime. Taking a vacation isn’t relaxing — it’s an opportunity to try things you’ve never done before.
A typical itinerary for one of our trips

Be prepared to fight for the value of slowing down

  • Your adventurer will be tempted to go-go-go, but you become their barometer for knowing when to decelerate. There’s value in slowing down and just having a relaxing weekend, and sometimes you just need to provide a gentle reminder.

Learn to love your bruises

  • Your adventures will cause you to wake up with bruises you don’t know where you got. Adventuring means not being afraid to get banged up every once in a while.

Embrace the fear

  • Adventurers live for those moments where your heart jumps up into your throat. It’s never about being fearless, but instead harnessing the fear to make you feel more alive.

Carve out some “Life Maintenance” time

  • Understand that your tolerance for adventure may be different than your adventurer, and that’s okay. Make it clear to your adventurer that you need a weekend every once in a while to sit in bed with some snap peas watching Sherlock BBC.

Experiences, not gifts

  • Your adventurer isn’t interested in jewelry or flowers. Try scuba diving or ziplining. Adventurers value experiences rather than gifts.

My mom makes fun of me from time-to-time because I was a self-proclaimed ‘inside-boy’ when I was growing up.

dat pose doe

My favorite past time was relaxing on the couch and watching TV.

But, sometimes all we need is a framework, a great example of how you can live your life to inspire you to be that person who you want to be, deep down.

Before you know it, you’ll find yourself caught in the current of a freezing cold river, riding a camel, mushroom foraging, curling in Vancouver, or handstanding on mountains.

Before you know it, you might discover that you’re an adventurer.

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