Food Truck Date #15: Know, When to Hold 'Em & Know When To Fold ‘Em (Or, My Progressive Lyft Food Truck Dinner Date) - 50 Food Truck Dates

Food Truck Date #15: Know, When to Hold ‘Em & Know When To Fold ‘Em (Or, My Progressive Lyft Food Truck Dinner Date)

Lovers, remember this – you can literally find a date in the most random of places and times. Just when you don’t think anyone’s paying attention to you, sometimes a boy is quietly crushing and will swoop in – so I’m here to tell you to always be alert and leave the house in pants. The end.

Such a thing happened with Food Truck Boy #15, my Lyft Boo. (A swooping boy who was quietly crushing, not ‘not wearing pants’).

It’s no secret to my friends in the Bay Area, that I have an obsession with Lyft – the on-demand ride sharing service with the quirky pink mustaches on the front of cars. I take Lyft to work, I take Lyft to and from happy hour, I even take Lyft at 1:30 in the morning when I’ve had far too many glasses of sangria and then force my Lyft driver to take me through the drive-thru of McDonald’s (At gunpoint, natch. Watch out after drinking Cha Cha Cha’s sangria. I mean, everyone should have the right to bear arms in force of drunken McDonald’s trips, ammm iii riiighhtt NRA?!)

Said forced-at-gunpoint Lyft driver found my 1:30am McDonald’s trip so intriguing, that he decided I was a girl he needed to hold onto, so he asked me on a date. When does THAT ever happen. I spent at least eight months trying to whore myself out to every cute Lyft driver I had, and then all it took was a trip to McDonald’s. (Gross). I’m officially giving up trying. Also, I can’t believe I’m admitting on the Internet that I ate McDonald’s. That wasn’t really me. That was my body double. I just swoop in on the date invites she gets.

Anywhosit, of course I immediately accepted a date with my Lyft Boo, and we decided to do a ‘Progressive Lyft Food Truck Dinner’ on our date where we’d take Lyfts to different food trucks throughout the Bay Area (his idea). Here’s a little recap, lovers…

Stop One: Meet ‘n Greet at Louie’s Bar & Grill

Lyft Boo and I decided to start our date out at a great little bar in downtown San Francisco called Louie’s, which just so happens to be in the alley behind my work (easy access is my middle name, lovers).

When I showed up, Lyft Boo scored some good first-date points with me in three ways:

  • He bought me a beer
  • He showed up with a backpack of costumes he’d brought and bought to wear in each of our Lyfts. I am obsessed with costumes.
  • He also brought me a little present (a little stuffed owl to sit on my desk). Random, but really thoughtful!

After a couple beers, we called a Lyft to pick us up outside Louie’s. Our driver was a good sport when he arrived to find us dressed in weird wigs and glasses. We wrapped a yellow feather boa around his neck and asked him to take us to the second stop in our Progressive Lyft Food Truck Dinner Date … Beep beep!

Progressive Lyft Food Truck Dinner Date

Progressive Lyft Food Truck Dinner

Stop Two: Off the Grid North Beach at Joe DiMaggio Playground

off the grid north beach

The first stop our Lyft driver(s) took us to was Off the Grid North Beach – a newer market on Off the Grid’s “food truck pod” scene each week. This particular one has about eight trucks, is held at the well-lit Joe DiMaggio playground and has a great family friendly vibe in the middle of San Francisco’s ‘little Italy’ neighborhood.

Lyft Boo and I did a quick circle walk around the trucks and decided on the Cheese Gone Wild food truck for the first course in our Progressive Lyft Food Truck Dinner. Something I loved right away about Lyft Boo was how ‘down’ he was for fun and craziness on our date, and he was just as much into social media and documenting the date as I was. Usually I try to tone down the picture snapping and Tweeting on my dates, and mostly keep my phone in my purse after snapping a few pics. Lyft Boo and I, however,  spent our entire date Tweeting, Vineing, snapping pics and being silly between costumed Lyft rides. I get that social media isn’t everyone’s thing, but it definitely added to the fun for me in this date! 

Progressive Lyft Food Truck Dinner Date

I also got a chance to know Lyft Boo a little bit more while we were eating our grilled macaroni ‘n cheese sandwich with bacon (!!!) from Cheese Gone Wild. Turns out Lyft Boo is an artisan mustard maker and is starting his own mustard line! How fun is that. He gave me an entire spiel about how mustard is the superior condiment (sorry fools, but I still think ketchup and ranch sauce takes the cake), and how our grilled cheese sandwich would be made even better with a smoked jalapeño garlic mustard. Mmmm, mmmm, mmmm.

cheese gone wild golden gate melt

But enough about mustard, it was time for us to Lyft off to the next stop in our Progressive Lyft Food Truck Dinner Date…

Progressive Lyft Food Truck Dinner Date

Stop Two: SoMa StrEatFood Park

Next, Lyft Boo and I headed to a personal favorite of mine, SoMa StrEatFood Park. It’s one of the best stops for a Food Truck Date because they have a beer truck the whole time they’re open, and everyone knows dates are always more fun with some liquid courage.

We decided to skip forward to dessert for this ‘food truck course’ of our Progressive Lyft Food Truck Dinner Date and tried the newer CandyBar food truck that boasts an impressive list of desserts such as fried mochi donuts, macaron ice cream sandwiches, homemade candybars like Butterfinger (!!!) and s’mores tart with salted caramel ganache and homemade marshmallows (which is obvs what I ordered).

I die.

jeanna barrett food truck

After dessert, it was time for us to head over to Berkley to FiveTen Burger, which was parked at UC Berkeley for the California Golden Bears basketball game. Since we were taking a Lyft all the way across the Bay Bridge for the last part of our date, we were able to snag the DISCO LYFT!! (It pays to be dating a Lyft driver with a hookup on the wayyyy coolest Lyft ride that usually is just a unicorn you get if you’re lucky to be assigned him in the app).

What is a Disco Lyft you say?! Oh it’s only the coolest, most rad tricked out car with lights and a sound system (including TVs on the back of the front seats and a karaoke system in the car).


So what did we do?! Well we freakin karaoked across the Bay Bridge, DUHHH. What else would you do in the DiscoLyft. This was by far the most fun part of the night. All cars should include karaoke systems in the back!! And of course I chose, “What’s Up?” by 4 Non Blondes as a homage to 1990 Jeanna with bad hair who sang that song at the top of my lungs in the front of my burgundy Ford Taurus with crushed velvet seats. What up, popular.

Stop Three: FiveTen Burger at UCBerkeley

A half hour and a few rounds of karaoke later, the DiscoLyft dropped us off at UC Berkeley for our final course in our Progressive Lyft Food Truck Dinner Date. I mean, shouldn’t everyone start a meal with mac ‘n cheese and bacon, then move onto marshmallow desserts and end with a burger and tots?! (Ermahgerd, why am I not 700 pounds).

fiveten burger sf

We jumped in line with the mob of college kids waiting for burgers and truffle tater tots from FiveTen Burger. The line was so long that we literally had to wait probably 45 minutes for our burger and tots, but hot damn, they were worth every minute of impatience. I don’t know if it’s cause I was beer buzzed and burger + fries are always the best drunk food, or if this burger truck is really that good. I’m going to go with a combination of both.

fiveten burger truffle tater tots

fiveten burger sf

AND, lovers, as if this night couldn’t get any better – we ended the night with a little karaoked Tony Bennet, “I Left My Heart in San Francisco,” as the DiscoLyft drove us over the Bay Bridge back into the lights of San Francisco.

Now, this would have been the perfect romantic, silly, weird, fun date on the planet.

But here’s one misstep I have to be honest about for the sake of allll single and dating men in the world (and the three who read this blog): Lyft Boo knew when to hold ‘em (me), but he didn’t know when to fold ‘em.

See, when we the DiscoLyft dropped me off at my house, he got out behind me. Whahhhhhhahah?! I was tired and wanted to go home, and at no point in the night were there any, “let’s continue this back at my house” signs. And then when I said, ” What are you doing? I’m tired and want to go inside” cause at that point our date was fourish hours long, he sorta begged me to grab a drink with him somewhere, and I relunctantly agreed after more insisting I wanted to go home and more begging. Then I was just kinda annoyed through the last drink (that I didn’t want to be drinking) and all I could think about was the couch I wanted to be on (not the conversation). Which kinda annoyed me, and once the annoyed girl switch is turned on, it’s hard to turn off. Hence no second date.

Wamp, wamp, wamp.

Listen to Kenny Rogers, gents: know when to hold ‘em (asking a girl out you find intriguing, cute or quirky for even the tiniest reason, is super hot and awesome), but you gotta know when to fold ‘em (don’t overstay your welcome, don’t beg, and certainly don’t follow her outside the cab to her door if there isn’t an invitation).

*P.S. Sorry Lyft Boo – you were amazing and fun and such a good sport, but just trying to keep it real. No hard feelings. Boop. XO*

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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.
20th June 2013
  • Anonymous

    What would your dating coaches say about this? Both your failure to put your foot down and your putting the responsibility for that failure on him and not yourself? Hmmmmm…

    • the50dates

      Hahaha!! Pretty sure my dating coaches wouldn’t say I failed by not insisting we didn’t get another drink. But I’ll ask em what they think! I also don’t think it’s off base to say it’s a failure for a guy to invite himself to outside your doorstep after a date. Sticking to my guns on that one, but thanks for your thoughts! xo

  • Mel

    OMG those Lyft vehicles crack me up!
    Also: MAC n’ CHEESE SAMMICH?!?!?! Wut.

    • the50dates

      I know! They’re pretty fun, huh? Maybe they’ll be launching in your city soooon Mel! :) And um yes. Grilled mac n’ cheese – so meta. Also had BACONNNN.