Food Truck Date #25: Into the Wild - 50 Food Truck Dates

Food Truck Date #25: Into the Wild

I stepped outside into the Oakland sun from within the depths of BART, the Bay Area’s underground transportation system, and turned left and right in search of a food truck parked outside to pick me up. I was a little nervous for the “production” of what was to come, and a little excited. At the time, I didn’t know I was moments away from a date that would constantly make me look back, smile, and remember why I started this whole crazy project in the first place…

For my special 25th date and commemorative halfway point, I had set up a date with someone who worked at Docs of the Bay, a burger truck in San Francisco. I wanted something different and special – the full meal deal. With my 25th date was going to come a tour of the truck - an insider’s perspective – and photographs from Behind the Food Carts to capture it all. So Docs wrangled one of their employees to agree to a date with me, and they (and he) were going to pick me up in the food truck and escort us to their Tuesday night parking spot for food service, The Kingfish Pub in North Oakland.

I squinted in the early evening sun and looked in both directions for a sign of Doc’s funky red truck with an image of a giant burger couch and the words “Serving Comfort in a Bun” splayed across the truck wrap. No sign yet of the truck, but a lanky, very bearded man sorta strut-strolled with a confident hop in his step across the crosswalk toward me with a gigantic smile on his face.

“You must be STEVE!” I proclaimed.

Steve and I had never met each other, but we linked arms and walked back across the crosswalk to climb aboard Doc’s food truck as it pulled up to the curb.

docs of the bay food truck san francisco

docs of the bay san francisco food truck

Kris, Doc’s Operations Manager, and Keith greeted me with tuxedo shirts – a little touch the truck crew likes to put together for special occasions such as catering, weddings or Food Truck Dates! How cute are they? (I want to smooch the one on the left).

docs of the bay san francisco food truck

The two of them fired up the truck for us and headed toward Kingfish. This was my VERY first time actually riding in a Food Truck (I did get a quick peek inside of Old World Food Truck on my date with Jewish Big Balls Batman), but I’ve never actually seen how these things operate. They really just are like giant tin cans on wheels with some cooking surfaces to cook the food! Squishy to ride in and rumbly when they drive – it was a hilarious start to a first date. Just me, Steve-O and two guys in tuxedo shirts listening in as we got to know each other.

docs of the bay san francisco food truck


When Steve and I arrived at the Kingfish Bar, Doc’s had rolled the red carpet out for us. In the middle of the divey Oakland beer & sports bar, they put up a little cafe table with a white tablecloth, flower napkins, a single red rose and a sign that said, “Reserved for 5:30.” They even had a sign that said, “Looking good Jeanna,” on display in the ordering window of the truck.

I was literally in awe – and felt like a real FTP. Food Truck Princess! (Not file transfer protocol). How HILARIOUS is it to see two people on a date in the middle of a dive bar with a white tablecloth and red rose. Everyone was staring and asking us questions – it’s a good thing I’m not shy! Usually I’m very anti-white tablecloth on a first date. As Behind the Food Carts captured in their interview of me, I prefer the ease of being outside and eating at a food truck on a first date to stuffy restaurants. So the ONLY way you’re going to get me sitting down at a white tablecloth with a dude on date numero uno is if you put the tablecloth in the middle of a dive bar that has old guys with beer guts belly up to the bar, and beer sloshed on the floor. ROMANCE, lovers!


It was at said white tableclothed table that Steve and I got a chance to know each other. The self-proclaimed “bad shaver,” is originally an Italian American mutt turned philosophy major, turned former organ repairman apprentice and organic trade farmer in Paris (whaaaa – is that sentence for real?!). Steve now works in Muir Woods in Marin County, cleaning up hiking trails.

I felt like he was a little nervous at first, and he admitted he had to psych himself up for a couple weeks for this date with me and all the photographers, but I immediately loved him for his easy going attitude and willingness to embark on something so odd and crazy with a stranger. There was something a little vintage hippie about him and a little wholesome, gentlemanly and young, yet inquisitive and smart as we chatted politics a bit (his favorite topic to discuss). Like me, he’s an over-analyzer who likes to dissect topics and, “but whyyyyyssss?!” Perhaps I too should have been a philosophy major… but, I digress.

I wasn’t the only girl charmed by Steve and his perfect giant white smile – there was a little girl who stood at the door of the bar, waiting for him to say hi and she shouted his name through the bar. Dressed in her pink dress, leggings and sparkle Toms, she wasn’t going to leave until she saw the guy she had a crush on who works the food truck every week near her house.

(Back off little girl, he’s MINE).

first date in dive bar

After our “getting to know you” chat and first two bevs to calm the first date jitters (I mean, some people say you shouldn’t drink on the first date, and I think that’s a BOLD FACED LIE), we moved onto my favorite part of the date – the FOOD, the tour of the food truck, and bar games!

I’ll write more about Doc’s of the Bay in my separate review post of the food truck, but I’ll start out by telling you, it is one god damn good burger. If I had one last dying meal, it’d be a comfort food cheeseburger, and I might even go so far to say, one specifically from Doc’s. They pair it with spicy green beans and/or fries covered in the best damn spicy custom seasoning I’ve ever had on fries. Steve and I tried everything on the menu and then washed it down with Doc’s fresh baked chocolate chip cookies and a couple rounds of shuffleboard. Steve had never played shuffleboard, but was a huge fan by night end, proclaiming, “I LOVE this game!”

Yeah duhhh. So glad I could pop Steve’s first food truck date and first shuffleboard game cherry. And I’m so glad he could pop my “neva been inside a food truck” cherry, giving me a tour of the truck and pointing out, “This is where we keep the green beans…”

I think our lives were both equally changed by the end of the night.

docs of the bay food truck san francisco

50 food truck dates




docs of the bay food truck

Somewhere in the middle of playing shuffleboard and drinking a few more bevs, Steve mentioned sometimes he gets told he looks like Christopher McCandless. Which cracked me, and all my friends up, when I showed them the pic. You guys, I was totally on a date with the reincarnated Christopher McCandless!!

For those of you who don’t know who Christopher McCandless is, he’s the main character featured in the book Into the Wild by John Krakauer - the biography of a young man who gave away his college scholarship and the American conventions of “graduate, then get a job, get married, then have children” to forge his own path. He packed very few belongings in a backpack and lived in the deep wilderness of Alaska, surviving only off rice, berries and what he could shoot with a rifle.

McCandless searched for a life that was different from the conventional – he wanted to change his reality, separate of what society found ideal and only centered around what he found ideal. He was seeking something that not everyone wanted, or had. He was trying to find what made him happy, traveling down his own path, making his own future.

And then I got to thinking as I traveled home from my date on BART …


It might be a super far stretch from Christopher McCandless starving in the Alaskan wilderness to me stuffing my face with cheeseburgers and cute men, but in some ways, I feel that 50 Food Truck Dates has been my own journey into the wild.

I wasn’t on the path of marrying my college sweetheart or 20-something boyfriend, and I found myself unhappy with dating in general and the process of waiting for boys to come up to me in a bar, or respond to my online messages, only to meet up for a stuffy dinner or awkward, boring date. So I moved to San Francisco, and I started this project to create my own ideal of dating and my own path to finding love. I wanted to change how dating was working for me – separate from what every other person and girl I knew was doing to meet a match. I was going to make my own way.

And here I am, a year later, being picked up by a food truck, escorted to a dive bar with a white tablecloth table and red rose, being served by two boys in tuxedo shirts and getting to know someone who was fun and interesting and adorable, who I never probably would have picked out online. It was a fun and silly and crazy date that constantly has me smile when I think of it, and I never would have discovered all of that if I wouldn’t have gone out into the wild of what dates can be.

So, I challenge you lovers – if you don’t like your dating life. If you’re single and lonely or bored. If no guys talk to you in the bar, if you can’t get a decent guy to ask you on a date or respond to your messages – take it all into your own hands. Make the future and the dating life you want, to find the love you want. And keep this in mind – you’re really only single a small portion of your life. We’re all constantly in a quest for love and the next best thing. But how long do you actually get to spend meeting strangers, and getting to know someone with a completely different background and life, and perspective than yours? You gotta make dating fun, you gotta create your own dating ideal. Because the quest for love sometimes isn’t easy, but you might as well have fun, and get to know where they store the green beans, while you do it.

docs of the bay food truck

(All photos courtesy of my good friends who have the most beautiful blog, Behind the Food Carts)

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About Jeanna

Jeanna's going on 50 Food Truck Dates - 50% for the story, 50% for the love and 25% for the food. That's more than 100%, but who's judging. Follow her food and date adventures in San Francisco and beyond by subscribing to via email or RSS.
7th November 2013
  • Behind the Food Carts

    Love it! Super fun to read your perspective on the night. Can’t wait to do another collaboration. Thanks for letting us be the third and fourth wheel for a bit.

    • the50dates

      Thanks guys. :) That was a SUPER fun collaboration. I wish I had your pics for all my dates!! xo

  • Mel

    Um, I don’t like bearded men (sorry, dude!), but this guy is extremely good lookin’ (is it the charisma?! haha). I also like the message that you learned and send out about dating. I hope that you feel recharged again on this project. Cheers! :)

    • the50dates

      NO WAYYY. Bearded dudes are the number one thing me and my girl friends hunt for on the west coast. That and Jews. ;) He’s pretty cute, huh! I am feeling recharged … now I just need to stop traveling for work so I can start doing some dates again!!