Food Truck Date #16: Twice is nice? Or...Are second dates impossible?

Food Truck Date #16: Twice is… Nice?

When’s the last time you went on a first date with someone, lovers, but then didn’t feel enough of “something” to put effort into a second date?

I find myself in a number of convos with the single and dating in my life where we agree that first dates are pretty easy – it’s the second date that seems to be the elusive holy grail a number of us singles can’t find.

Has it really become that hard for two people to connect or find someone compatible? Or have we all just become a little too picky and lazy with dating that going out with someone we feel lukewarm about is too much work in a world where sometimes we’re so busy, it feels difficult to find time to pick up bread at the grocery store…


A couple months ago, I found myself solicitating the advice of a couple fabulous dating coaches who so eloquently told me that I was waiting for the equivalent of the Halley’s Comet of Love. One of the points we touched upon in our little Google+ Hangout coaching sessions was that I’m entirely too picky and think I “know what I want,” which actually leads me to rejecting a lot of guys too quickly (after the first date) when love sometimes develops after the second, third or even fourth date!

[Wamp, wamp, wammmpppp Jeanna. Get it together.]

I’ve thought a lot about that since because some of my most favorite couples in my life didn’t actually even start to like their significant other until date two or beyond, many of them even “grew” on each other. We all have those relationships that we slightly envy and want to emulate our next love after (I mean, yours might not be Kim and Kroy Biermann, but WHATEVER).

Personally, I have a handful of friends who are so in love and such a great match with their significant other, that I can only hope and dream to find that for myself one day. One particular friend of mine confided to me that after her first date with her now husband, she neverrrrr thought they’d end up together. She thought he talked too much and was pretentious! Ha. Now, they’re one of my very favorite married couples who are the most fun to be around and recently welcomed a little boy into their lives.

What if I’ve already rejected someone who could have turned into a great love and future future baby daddy?! 

These are some of the things that keep me up at night.

i careSo, I’m trying so hard, lovers, to stop being too picky and focus on opening my mind and heart up to men who might not come across as my “perfect dream boat love match” within the first thirty minutes. I’ve started to focus on going into every date and finding what I LIKE about each guy, rather than what I DON’T like. It’s amazing what can happen with a little perspective change, right?

All this little self improvement and change in attitude was happening right around the time I met Food Truck Boy #16, The Nerd, for our St. Patrick’s Day date.

So in the interest of not being too picky or rejecting guys too early, I focused on what I LIKED about The Nerd our entire date.

First and foremost – I liked that he’s a ‘nerd.’ Big nerd love comin’ outta this girl here.

I liked that he showed up in a cute yellow zip up hoodie and Vans in a comfortable, casual and cool non-hipster way.

I liked that he works as a UX Designer because I’m a geek about apps and design, so we could wax poetically about our jobs.

I liked that he was very NICE and didn’t have anything negative to say or have overly strong opinions I didn’t agree with, even if he might be a little too shy and introverted for me. Even if I felt like I talked wayyy more than him, and EVEN if I’d probably eat him alive with my bold, brash personality.

I liked that he was willing to try the new El Calamar Peruvian food truck because he hadn’t had Peruvian food before – to me, this shows a sense of adventure. There’s nothing worse than someone unwilling to try new things. AND I liked that he was okay with splitting our food – I love trying every dish and getting down to the business of luuuvvvv over a shared meal. Also, who wouldn’t expect the best kinda love to blossom over a green beer and my favorite Peruvian dish, Lomo Saltado?!

lomo saltado peruvian

So what if there didn’t seem to be too much chemistry right from the start, that the conversation was sometimes sticky, and that it felt more like friendship than love. I was going into this with a, “YOU GET A SECOND DATE. AND YOU. AND YOU. AND YOU,” mentality.

I liked this guy enough to pull out a tiny nugget of possibility. A second date possibility. A ‘he could grow on me and we could fall in love and he could be my FUTURE FUTURE BABY DADDY” possibility.

Am I losing my marbles, lovers?

We both left the date very politely with lots of “let’s hang out agains,” and “I’d love to meet your friends,” or “let’s do beers and pool at a dive bar in the Mission.” But when it came down to brass tacks, neither of us texted after the date of followed up with email or any contact that said we had a good time.

I guess sometimes two lukewarms do not a second date make.

BUT, I’m still going to focus on keeping my mind open to second date love possibilities and toning down the quick judgement and need to reject.

Secretly though, I’m still on my quest for the holy grail of dating – the elusive second date with someone I feel gigantic, fly me to the moon, take my pants off now, let’s make babies and never leave each other again SPARKS (shhh, don’t tell my dating coaches).

Well, at least someone who sounds better than Snickers ice cream on my couch while watching Kim and Kroy on Bravo.



What do you think – would you go out again with someone you’re lukewarm about? Or should we all wait around for sparks and fireworks?

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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.
11th July 2013
  • Dougomite

    Awww, all that talk about how you were giving out second dates like candy…and still no second date for The Nerd. I am disappointed. On the bright side, I was on the fence about going for a second date, after a luke warm first earlier this week, but your post has convinced me to give it a shot. So we’ll see if two luke warms with a dash of effort makes a second date.

    • the50dates

      Well, I would have gone on a second date with him, if he would have asked me or acted interested! (Often times I shirk the invite or say, no thanks) That’s why I said a second date doesn’t work when the other person is just as lukewarm as me. :) I’m glad you’re going to go out with the lukewarm girl again! Let me know how it goes.

      • Dougomite

        Second date went great, turned into an all day and going out that night date.

        I’m thinking that I’ll start thinking of first dates as a “Can I stand being around you for more than an hour?” checks, and for no red flags. Second dates seem like the real “Can I be around you and enjoy myself” check. I feel like only the really good first dates definitively answer both questions.

        • the50dates

          Bada bing bada BOOM. That’s awesome to hear!

  • Brittany

    Love this Jeanna!!! I am about ready to marry (10 days or so) a guy that I was only lukewarm about at first! I liked him enough to agree to a second and third date but on the first, I was like… I dunno about this cat! I was super judgy and thought of all sorts of reasons why we might not work out, but he was really nice (and cute), so I figured I would see where it went. And look where we are today! Crazy. It took me while to get over my judgy baggage, but now I am about ready to marry the most wonderful man I have ever met. Seriously. I am so thankful for him.

    If I have any advice, give them a chance before you decide that they are too weird, or to pretentious or too into their work etc for ya. And sometimes you have to quiet that crazy person inside you that thinks there should be an explosion of fireworks when you hang out for the first time. Just know that sometimes, it comes later :)
    thinking good thoughts for ya :)

    • the50dates

      Seeee, I LOVE THIS Brittany!! I hear these types of stories over and over, so this is one of the major lessons from the last year that I’m trying to keep in my mind. I think there’s a bad wrap with having someone grow on you. And I actually thinks it helps when the girl just “isn’t that into” the guy at first cause it tones down the crazy that makes guys run in the opposite direction. :) Thank you so much for the kind words. I’m so excited you found your BIG love and can’t wait to see pics. I know you’re going to make a gosh dang beautiful bride (with yoga arms). ;) xoxo

      • Brittany

        Definitely toned down my crazy!! haha. I was into some other guy, and my fiance totally grew on me. My mom actually pushed me to continue to explore it (thanks ma! who would have thought!). It wasn’t until date four that I realized there could be something awesome here.
        I have loved following your journey, and am so excited for the blog post “so I think they could be something here…” : )
        Would LOVE to see your beautiful face back in Seattle sometime soon. xoxo

  • Sarah Alway

    Hello from the girl who eventually married the guy who she had no interest in, initially. So it can happen! :-) I do think that with anyone (friendship or romantic relationship) there’s something to be said about clicking immediately or not. I definitely clicked with Stew as a friend and then lucky for both of us it turned into something more. Go with your gut, Je!