30 Dates with Yourself – Date #20
“Eureka! California here I come!”

It’s been 7 months since I took myself on a date to California.  I can hardly remember what I did yesterday, let alone 7 months ago, but I’m not giving up on this journey.  I’ll have to do some back-tracking, but with 8 more dates to go, I’m almost there!  I will complete this experiment.

I saw every episode of “The OC” when I was in my early 20’s so all I can hear is the song “California” by Phantom Planet in my head as I fly across the country to the famous state of California.

I’ve always wanted to go to California.  I’ve always been in love with the state even though I have never visited.  So as when December 31st rolled around and I was writing my 2017 goals, I finally put it in writing.

“Go to California for the first time.”

November 2017 came and still had not been to California.

It was time to make it happen. I had a little over 30 days to complete this goal by the end of 2017.

Pitch Night

I had signed up for a 2-Day Launch Camp in November, called Seed Spot, to pitch my “30-dates with Yourself” concept and explore the idea of turning it into a business idea.

I worked tirelessly for 2-days coming up with a concept and pitch.  It was exhilarating and something I have never done before.

I figured a trip to California immediately after Seed Spot would be the perfect time.  I’d be inspired by the entrepreneur camp and could use the momentum to keep working on my new idea in California.

On the airplane!

I didn’t sleep for 2-days working on my concept at Seed Spot and the next morning, I headed off to the Golden State.

California here I come!

I booked a vacation through Southwest Airlines Vacations and found a fantastic deal to stay at Paradise Point, a San Diego Island Resort. This was a unique resort with little bungalows spread out throughout the entire island.

A cute California dude drove me in a golf cart to my bungalow and I could feel the windy California wind on my face and taste the Pacific vibe.

I sat on the edge of my bed in the bright bungalow that faced a lagoon filled with lily pads.  I did it.  I made it to California!

Traveling with yourself is a great way to see what you like to do on vacation.  Often, we get caught up in what we’re supposed to do on vacation or what those with us want to do.

We listen to the bartender tell us what restaurants to eat at.  We listen to the concierge tell us what adventures to sign up for.  We dust off the big book of “Things to Do in…” in the hotel room and let it decide where to go.

But what do we want to do?


I’ll never be that person who has an itinerary on vacation. I wish I could give you an elaborate report about all the amazing trips I planned and the adventures I completed while visiting San Diego, but the truth is, I just putz around.

It’s what I do best and it’s what I enjoy.

I explored what the city had to offer and took it in, moment by moment.

I had breakfast on the water every morning, I enjoyed nature with no intentions, I read by the pool for hours, I went for walks, I drove around Coronado, walked the boardwalk in Pacific Beach, drove by the obstacle courses at the Naval Amphibious Base, had dinner with an EOD specialist in Imperial Beach, met a retired navy rescue swimmer who opened a store that only sold WATER, yes just water!  I watched hippies walk a tightrope at the park in Ocean Beach, enjoyed wine late night on the docks, bought a touristy California sweatshirt, and many other little adventures.






One of the gifts of staying up for 2 days and then packing for a trip to California is being delirious.  For some reason, I packed my suitcase like I was going to Florida in August.  Not a trip to California in November. My suitcase was filled with swimsuits, a few sleeveless dresses, tank tops, shorts and flip-flops.

It was 40 degrees.

It was pretty much freezing the entire time I was there.  On top of it being November, they had gotten a cold front. I somehow packed a snow hat, so at least my head was warm.

I wore the same sweatshirt and black Lululemon yoga pants the whole time.  Thank goodness I get cold on airplanes because that outfit saved me.

My favorite day was a windy day in Pacific Beach.  After breakfast, I opened up my good ‘ol Tinder app and said I was looking for someone to show me around town for the day.  30 minutes later, I met Dominick, a local who was the perfect gentleman in showing me a California adventure.  I told him I wanted to do a few touristy things on the boardwalk and wanted to see California bluffs.

But Anna, I thought you were dating yourself?  I am.  And I also get to do whatever I want to do.  That’s the beauty of dating yourself 😉

I wanted some company and I wanted someone to show me around.  We rented skateboards and scooted around as I admired the oceanside boardwalk.  We parked our boards after working up a sweat and he suggested I try the famous Vodka RedBull Slushy at Pacific Beach Shore Club.

Day drinking?  Sure why not!  I’m on vacation!

But my day was made after we left PB Shore Club and Uber’d to La Jolla, CA.  We headed to Torrey Pines Gliderport to hike down to Black’s beach. 


This hike down the California Bluff was exactly what I was looking for. Challenging, yet simple enough to do out of the blue, it was perfect. The view itself took my breath away. And later, the hike did as well.

Once you accomplish the steep hike down a winding path of natural and manmade steps along the cliff face, it feels like you have landed on an untouched secret beach. 

But this beach has definitely been touched and Black’s Beach is best known for being a nude beach.  It was cold so there were only a handful of people exploring the beach, but it was such a cool spot.  And for the record, my sweatshirt and yoga pants that I had been wearing for 2 days, stayed on 😊.

I told Dominick about the dating experiment I was doing and wrote Date #20 in the sand.  I took a few pictures, soaked in the water, and we headed back up the bluffs.

Half-way up the climb, I filmed a live video of myself doing burpees on the bluffs and completed the rest of the hike.

I thanked Dominick for a perfect day and was happy to officially made my first friend in California.

I did a little shopping that night looking for souvenirs for my daughter and headed back to Paradise Point.

I had the Uber driver stop at CVS so I could pick up a bottle of wine and some sweet potato chips.  After he dropped me off, a classic Anna moment happened as I realized I locked myself out of my bungalow.

So, there I stood in the middle of the night, with no key, on an island with a bag of chips, a bottle of wine and no wine opener. The resort was huge, so it was about a half-mile to walk to the main office to get a key.  I laughed at the situation, opened my bag of chips and walked across the street to enjoy the water view from the resort’s shoreline.  I just sat there and smiled, eating my gigantic bag of CVS chips and breathed it in.  When I was ready, I headed to the front desk to get a key.

When you’re dating yourself, you get to fall in love with your quirks.  Noone is there to roll their eyes and tell you, “I can’t believe you lost the keys….again.”  So what?  It’s not a big deal to me.  I enjoyed being locked out for a little while.  I had a bag of chips and a million dollar view!  What else can you ask for?

This is how you fall in love with yourself.  So next time you do go to a resort with a date and lock yourself out, you won’t be embarrassed or let someone put you down.  You now know yourself a little better.  You accept your oddities and love yourself anyway.  And if someone hates that part of you, well then, …it’s Bye Felicia.  (I’m laughing because that is the first time I have ever used that slang term!  It’s funny, but I don’t think it’s my jam.  Seemed to fit there though 😊)

This trip taught me how I like to vacation.  I’m not a planner and I like to wing it while I’m visiting somewhere.  It also taught me that I’ll probably need a partner that is a planner.  There were many things I wanted to do, but I couldn’t seem to wrap my head around the logistics.

Next time I come to California, I’ll come with a date so he can plan out some amazing adventures we can do together!  I’ll stay in charge of not-planning the spontaneous mini-day-trips and of course, losing our hotel key.

If you haven’t traveled to a city you’ve never been to on your own, I highly recommend it.  You learn a ton about yourself and how you like to travel.  And that’s the whole point!

What if all this time you have traveled a certain way just because that’s the way your partner or family has traveled?  Maybe you hate hotels and would rather stay at a bed & breakfast.  Maybe you prefer ordering room service over 5-star dinners.  Maybe you like historical site-seeing instead of outdoor activities.  You’ll never know till you try it all, so get out there and see what YOU like!

Until next time…

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