The Timing Will Never, Ever Be Right - 50 Food Truck Dates

The Timing Will Never, Ever Be Right

I’ve spent the last two months thinking in my spare time a lot about 50 Food Truck Dates: where it started, who I’ve met, where I want to take it, and because I’m a perfectionist – a lot about mistakes. I have a one-year recap draft that I keep visiting and revisiting, trying to capture exactly my state of being and heart right now to share with you. Except I keep getting hung up on one person. Maybe not so much him specifically, but how he marks a pivotal turning point for me with matters of business and heart, so I thought it only best to tell you about him and how he’s led me to where I expect to go in Year Two…

I have huge hesitation in writing about this person because I get a little twinge of hurt every time I think about him. And I tend to push back hurt and failure to that part of your brain that masks really FEELING. The part that makes excuses, brushes things off and explains with a flick of hand, “Oh, I’m just burnt out.”

But, instead of pushing this back, I’m going to tell you how someone hit me particularly hard, and has left me with this overwhelming sense of burnout. It’s not necessarily what he did, as much as he was an accumulation of every man this past year, every dating disappointment for the last 5+ years. Of not getting what I want, not knowing what I want, and not knowing how to express what I want. Especially not knowing how to express what I want. Years of staying silent, playing cool, and not saying what I mean. Of getting wrapped up too many times with guys who want casual sex, or to spend all their time with me, but nothing more. Too many guys where the timing wasn’t right…

It all kinda just became too much, and caused me to step back from this project and look at what I was projecting, and the tiny non-truths I might have been telling myself and others as I try to act strong all the time, mask feelings, and brush off hurt with a flick of hand.

dating communication

He might read this, and that alone makes me cringe and hit delete, but one of the main lessons this story has helped me reach is that I’m never going to personally succeed at this project if I’m not honest with my feelings, to myself, to those I date, and to my readers. Despite seemingly running a blog about dating, being honest about my feelings is the hardest thing for me – I often don’t tell even my closest friends and family about who I love and why I love. And I especially don’t tell boys. I guess when it comes to matters of the heart, I keep them close to my heart. And when it comes to how we met, what unfolded and how he treated my heart, I guess his timing just wasn’t right.

I only spent three nights with him, but in just three nights I could tell he was a smarter, brighter star than most. A bright star who overthinks things, who wants to be the best at everything, and who therefore might be a little too hard on himself. Who is quiet and a bit introspective, but also such a great communicator that no one dislikes him because he listens when he needs to listen, and he laughs, and he’s just witty enough, just romantic enough, just nice enough. A bright star who’s creative – more creative than his job allows. So he seeks beautiful creativity in other pockets around him – in songs, in making music, in drawing in a notebook he carries around. His aspirations and drive are big and bold – of traveling, of charity, and of getting the job he wants most that he’ll stop at nothing until he gets it. I know this because he once told me a big belief he has in his life, and then quoted my own life mantra back to me – find out what’s making you unhappy, and change it. He also once took my hands and said, “How do you feel about us… I don’t get this serious with other girls.”

I laughed it off, “Us?! What do you mean.”

And then I changed the subject… after all, masking your feelings, pretending you’re not interested, keeping casual – this is the name of the game I’ve played too long to know how to play any other way.

What I should have told him is that I knew after date one that there was something between us that doesn’t come along for me very often. I know that I’ve spent years kissing boys who don’t amount to much. That I’m searching for something I can’t quite place my finger on, but I do know it is, and he is, slightly reminiscent of the someone I once loved, or will love. Slightly reminiscent of good music and books, the ability to talk about what makes you tick, frustrations and the faults in the world. About how you want to be bigger, better and brighter. Slightly reminiscent of dancing in the dark, of chemistry that makes your heart beat and floods your veins. Of words that can’t come out fast enough – a history you can’t share quick enough because you just want him to know everything about you because he understands. Reminiscent of standing on a city corner as cars and lights rush past and all you wish is for time to stand still so you could have one more conversation, one more drink, a little more time to study the way they take your hand, and seem to know you before they really know you. And how each time you let them know you a little bit more, it feels like a deep dark hole you could fall into and never out of again.


Just three nights and a few months of casual friendship texts and emails, but I still kinda ‘fell’ for this person. Whatever ‘fell’ means these days – more than liked, more than friendship, somewhere between I want to spend more time with you and all my time with you. But, this someone wasn’t right for me – but not in all the ways that “not right” usually means when your friends tell you, “That guy isn’t right for you.” Not right as in - our timing will never, ever be right.

He told me he didn’t want a relationship, that he just wanted to have fun. Nothing more than casual. The honesty is that I’m just not IT for him. I don’t know that he’s had enough time to reminisce on who he has or hasn’t loved, what he’s looking for, what he wants. Not enough years kissing girls who don’t amount to much. Maybe too many years kissing girls who do amount to much – and not enough years being careless. Age might be just a number, but it means I know when I’ve met someone you don’t let go of, and he, he might not. Or maybe I just wasn’t enough of a bright, shiny star for him. Maybe three nights weren’t enough.

Whatever it was, it’s okay. Sometimes things are a bit more one-sided. But here’s what I did wrong – I told too many non-truths to him. A big one: I’m okay with keeping it casual. And the biggest: I don’t see us getting serious.

I realized as he pushed away, and I had hurt feelings from unreturned texts, canceled plans and weeks of silence that I was never going to be a part of his life as much as I wanted him to be a part of mine. But I had lied and told him that my expectations were low, and I could deal with a casual brush in every time he felt the need. That we could talk about our lives and I’d show him a good time, and I wouldn’t care when I didn’t know what happened to him, when I didn’t see him again for months. That I’d be there for skips around bars, vodka sodas, and late night makeouts. But, I knew that every time he left, I’d want more. He was never going to give me what I wanted. And funny, I never even told him what I wanted.

I should have told him:

I can’t lie next to someone in the dark, staring at the ceiling and talk about what we do when we can’t sleep – and keep it casual. We will never be casual. I’ve been casual with those who just aren’t there for me. But you, you’re there.

But instead I told him it was best we stayed away from each other.

Three days – this is how quickly you can ‘fall’ for someone. How quickly you can ‘know’ them. And how quickly you can know that you need to walk away. Because it’s all been too much, and you need to change. Because if you’re being honest – it’ll never be casual, and the timing will never, ever be right.

timings a bitch

So there we go. Some of you ask if I’ve met someone through 50 Dates, if the project is working – and I can tell you: Yes, I met someone, he was spectacular, we had a brief fling, and it didn’t work out. But he’s helped me see more clearly what I’m looking for, and I’m no longer going to apologize or lie about the fact that I want something more. I’m tired of casual, commitment-free dating. I’ve kissed enough boys to last me a lifetime, and if I find someone I want to spend more than two hours with, then I want to hold onto that person and spend four hours with them. And I want to write openly and honest about it. I don’t want to worry about what he’ll read and how he’ll interpret it. And I want to tell him openly and honestly what I want, what I need, and if he is or isn’t there for me. So, that is the foundation of my lesson this past year… more to come. 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.
30th September 2013
  • Mel

    YES! You learned the most important lesson of all: being honest about your expectations in relationships. It also took me far too long to realize; this, after also playing the “I’m cool and taking things casually” partner.

    Believe me when I tell you that once that honesty happens, you WILL meet the right person. And yes, it can happen FOR REAL in three days. My current relationship moved VERY quickly; ahem, he packed a bag on the first date… and he’s never “unpacked” it. :)
    I KNEW something had to have happened to this 50 Dates story, and I’m glad you decided to post about it. THIS in itself is cathartic. And I’m even happier knowing you’ve now realized what’s important and necessary for YOU. <3

    • the50dates

      Why does it take so long for us to learn to be honest with our expectations?! I was talking to one of my BFFs about this – us girls are taught that we’re overly emotional, crazy, and are always trying to act cool and supress our feelings. DUMB. I’m over it.
      Thanks Mel for the confidence. I LOVE that you and your boy never left after date one! WOW. Crazy. And yes, it is all a bit cathartic and necessary, huh? :)

  • Nope

    Stop calling/thinking of them as boys and they’ll stop thinking of you as a girl.

    • the50dates

      Well appreciate your opinion, but NOPE. Boys is just a word. Men is just a word. It’s really TOMATO TAAAAMATO. They’re all adults. How about I just refer to them as adults? I met a fine adult last night, we went on a date, the adult didn’t call me later. Damn him.

      • Nope

        You’re the expert, you’ve found what you’re looking for. Don’t change a thing.

        • the50dates

          Stating that using the word BOY is keeping me from finding love is a laughable theory. Where’s you find that, the Land of Shitty Theories, right next to “the earth is flat”?

          • Chef BOY-r-dee!

            When you find your dreamboat, make sure you introduce him as your manfriend, not boyfriend.

    • BOY Crazy!!

      Nope, have a drink and enjoy our life. Make sure the glass is half full!!!

  • Sarah Alway

    Oh my gosh Je, what an amazing and honest post! It made me feel a little sad, amazingly proud, and super lucky to have such a fantastic person like you in my life. Obviously honesty is usually the best policy, but when you’re blogging or writing in any type of a public forum, it can be incredibly difficult. You feel as though you’re writing for an audience, and that audience has expectations… of a beginning, a middle, and a happy ending or something. But that’s not the way life works, and I think hearing about your struggles, vulnerabilities, and self discoveries makes you so much more REAL than so many other people I know or read about. You deserve love more than most, and when the time is right you’ll find it. Promise!

    • the50dates

      Thank you Sarah! Being honest IS the hardest part for me in all this. And I know that honesty is what readers want to read and hear, and what makes my journey most interesting. But YES, good lord – when every friend, family member, coworker and boy you’ve dating is reading along, that’s a lot of judgemental eyeballs! So it’s taken me a long time to get over it. I’m really wanting to head into the second half of this project with a focus on honesty though, so here’s hoping I continue to get the courage. Thanks for your continued support and kind words that I deserve love. Means a lot. xo

  • Kelly@Running Blonde

    I am over the moon excited for what is in store for you over the next several dates! I’ll be living vicariously through you for sure!


    How I Met Your Mother has a quote on Timing & Chemistry. And JFYI, you can learn this valuable lesson, write about it, talk to your future partner about it. . . . but practicing it is harder (for me). I literally feel like I have to write up a contract with myself to NOT participate in committment-free dating. Its an on-going challenge since I have realized the same things as you. Keep up the good work!