Dating On The Rocks Of San Francisco

Dating in San Francisco sucks with most first dates being like Groundhog’s Day. We meet at a bar, grab a drink and then have that awkward “so why are you single?” conversation. So when Gavin* asked me to go hiking at Lands End for our first date I was game ready for something different.


Excerpted from Trails of San Francisco map

Shamefully I had heard of Lands End, but had never been nor did I have a clue exactly where it was located in the city. Whatever, I figured I am an adventurous gal, he was super cute and we hit it off immediately when chatting online so what did I have to lose? Well, my life according to
the Safeway employee who helped me pick out snacks for the hike. Granted he had a good point, the possibility that I may have found a decent guy on OkCupid outweighed the risk.

We met at the Legion of Honor where he guided me down a very long stairway to our urban adventure. Halfway down what seemed like over 100 steps, we discovered a hidden labyrinth. Jokingly I said it was created by aliens, but was quickly corrected by a random stranger that it was actually Eduardo Aguilera.

After a quick attempt to solve the maze, we continued down the steps until we reached Mile Rock Beach. This rocky beach with its crashing waves has breathtaking views of the Golden Gate Bridge and remnants of previous shipwrecks. I liked that Mile Rock Beach was deserted giving us time to stop and chat as we hiked. The one thing that was a bit odd is that we kept stumbling across pieces of an abandoned building with some interesting graffiti throughout our hike.

Mile Rock Beach, San Francisco

location where I almost fell

If you are going to adventure out to Mile Rock Beach I recommend coming right before sunset to get some great pictures. The only caution I give is to stay on the paths and my #1 dating rule — Always Follow Your Instincts. Gavin, an avid rock climber, suggested we go off the beaten path to leave the beach and we hit a small stretch where the ground was not stable. When I attempted to cross this section I momentarily lost my footing and courage to move. Convinced that falling to my death would definitely be my worst first date and embarrassing, I found the will to move and finish what ended up being one of the best first dates.


*Name changed to keep his identity private



An eclectic, world traveling sista from San Francisco expressing 'Rogue-Thoughts' on food, travel, music, fashion and living an authentic life unapologetically.


  • Reply May 15, 2014


    Sounds like a great first date. It even encourages me to get back on OKCupid!

    • Reply May 15, 2014

      Danielle Washington

      I think online dating is like the lottery, you hate wasting a dollar or more each week, but you gotta be in it to win it. Good luck Rachel in your dating adventures and thanks for commenting on this post!

  • Reply May 15, 2014


    Nice post! Sounds like a great date and you came out of it with a cool perspective. I read somewhere that psychologists say doing heart-pounding activities together helps two people bond. It’s that adeline thing.

    • Reply May 15, 2014

      Danielle Washington

      If that’s true, we are destined to have a strong bond as both of our hearts were pounding when I almost fell. :-/

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