381. an unexpected (lenten) journey

Alternate title for this post: Bob redux (part 3)
Part 1
Part 2


I’ve been in a writing frenzy these past few weeks.

That little crying spell did quite a number on me – a lot broke open within me, a lot of really old, hidden longing and discontent and anger.

But in a strangely ironic way, all this outpouring of angst and bile was prompted by an initial glimmer of hope – a hope that I want to remind myself of.

And that’s the topic of this (likely last) installment of the posts about Bob.


A few weeks ago, I posted this tweet:


Honestly, I put it up as kind of a joke. I didn’t actually mean it at the time.

And then I thought about it. And then I realized that it was actually kind of a good idea. And then something really unexpected happened.

The (emotional) shit started to hit the fan.

Again, some backstory is needed here to give you some context.

For just about all of my adult life, I’ve had terrible self esteem issues when it came to dating and relationships. Back in this very early post I described myself as someone who

accepted the thought that for whatever reason, I was chronically unappealing to women. I thought that perhaps because of some genetic defect, instead of releasing come-hither pheromones when attracted to a female, my body released a subtle, toxic go-yonder scent that made it impossible to hold the attention of anyone I was remotely attracted to.

There’s low self esteem, and then there’s self loathing. I used to have a really bad case of the latter. Let me share a brief story to illustrate how deep this loathing went.

Photo by: Adam Foster

Photo by: Adam Foster

Back in 2007, I had just moved to Seattle and was just starting to attend Quest Church. And that’s when I started to notice someone I came to call Quest Girl. She was smart, pretty, funny, fun – in short, she put the rush in crush (LOL). When I joined up with one of the church’s Bible studies, I ended up going to the same one she did (not entirely coincidentally).

Like most Bible studies, after the formal study portion is done, people hang around to mingle and catch up with friends. So a few months after joining this group, during one of these social times, Quest Girl walked across the room to where I was and started small talking. To me.

This was the first real conversation I had with her, so it was all really surfacy, chit chatty conversation. But you know how in small talk there are these pauses where two people normally break off the conversation and move on to talk to other people? There were a bunch of those pauses between Quest Girl and I, but here’s the thing. She didn’t move on. Each time one of these awkward lulls in our talk would crop up, she’d just stand there – sometimes looking at me, sometimes down at the cup in her hand. But she’d stand there until she or I (it was usually her) would find some other politely bland topic to chat about. And then there’d be another pause. And she’d stay standing there. And then we’d talk about something else.

It was painfully obvious (even to someone as utterly clueless when it comes to signs of attraction as I) that she was waiting for me to do something – something like asking her out for dinner or drinks or coffee/tea or walking her out to her car or asking for her number – something, anything!

But I just stood there like a fish, opening and closing my mouth as empty, insipid bubbles floated out.

Photo by: Luca Cerabona

Photo by: Luca Cerabona

My problem? On the inside, my brain was melting down. It was a train wreck up there. In addition to the “hurricane of terror screaming at me to bolt for the door” that I talked about in this post, there was something else in play, utterly frying my synapses.

Looking back on that time now, I believe I was suffering from an extreme case of cognitive dissonance – a condition where a brain tries to hold two contradictory beliefs at the same time. It’s like this. When you try to hold two magnets together with the same poles facing one another, the poles repel and it’s impossible to get them to touch. The stronger the magnets, the stronger the repellant force. While Quest Girl was standing in front of me, almost pleading for me to ask her out, my brain was struggling to bring together two opposite and opposing ideas:

Women I’m attracted to never find me attractive or want to go out with me.
I’m attracted to Quest Girl and she’s wanting to go out with me.

As hard as it tried, my brain could not hold these two ideas together but it also couldn’t let either of them go. And so in the midst of that struggle, it’s no wonder that it wasn’t able to string together these seven simple words: “would you like to go out sometime?”

Can you see how strong my doubt about my desirability was? It was so powerful that even when this woman that I had been crushing on for weeks was standing right there in front of me, signaling in no uncertain terms that she wanted me to ask her out, I still couldn’t overcome the belief that I was unwanted, unattractive, undesirable.

That, my friends, is what a shit ton of self loathing can do to a man.


Image from PostSecret

That was six years ago. Many things in my life have changed since then. I’ve worked through copious amounts of bad theology and shallow church teaching. Years of counseling have helped me work through a number of unhealthy self-denial patterns and relational issues. But this fear and loathing attached to asking women out goes WAY back – even before the church heaped guilt and shame on top of things. I’ve simply had really shitty luck when it comes to women, a trend going all the way back to high school. (In particular, one short-lived relationship that turned out especially awful early in college left me acutely cynical about me and my self worth.)

The law of averages have not been kind to me when it comes to dating.

And so, to return to the tweet that I started this post with – “This year for lent, I’m going to give up singleness.”

That tweet was a direct result of finishing a post where I was able to identify why it was that in the past few years, I was always abandoning relationships with women just as the relationship was getting good. That was quite a breakthrough for me and I was eager to get myself back out into the dating world to see if I could do different. I started to ask women out (yeah, plural). So I sent out the tweet in a kind of triumphal, celebratory pronouncement of my newfound dating bravado.

And then…

And then all those old fears and feelings of self-loathing started to creep up again. I found myself thinking very old, very cynical thoughts – thoughts like,

“yeah, maybe she said she’ll go out with you but that’s just a sympathy date. She’s gonna dump your fat, ugly, repugnant ass the first chance she gets. I mean, why the hell would anyone want to have a relationship with you? I’m telling you, that was just a sympathy “yes,” not a real one, so get over yourself.”

And if you can’t tell from the context, thoughts like that pop into my head right after getting off the phone with someone who just agreed to go out with me.

It happens that fast.

Photo by: Leeky-Boy

Photo by: Leeky-Boy

In the following days and weeks, as doubt and fear about dating again swelled within me like a mushroom cloud, I started sending out tweets like this:

I want to believe, but… (Mark 9:24)

and this

The problem with wrestling with hope is that it doesn’t put up much of a fight, even (maybe especially) when you need it to. #whereimat


But then I started to see Quest pastors tweet things like

Lent is not meant for a 40 day challenge but a changed life. (Pastor Aaron)


When you give up something, replace it with something beautiful. Removing weeds without planting something…only produces more weeds later. (Pastor Eugene)

And then I went to Quest’s Ash Wednesday service where, upon the imposition of ashes, these words were spoken over me: “Remember that you are dust and to dust you will return.”

And all of these lenten affirmations made me realize that this season really is an opportunity for me to take this liturgical season and my tweet about giving up singleness with the utmost seriousness. I also realized that it wasn’t necessarily singleness that I was giving up for lent, it was the debilitating cynicism regarding my singleness that I needed to fast from. I could choose to silence (or ignore) the voices trying to convince me that I’m undesirable. I could choose, instead, to believe that I’m awesome – that I’m so money, I don’t even know it.

Pastor Aaron’s tweet reminded me that I could take up a new conception of life and Pastor Eugene’s tweet challenged me to replace my self-loathing with self-belief. And the Ash Wednesday liturgical phrase reminded me that “…it comes down to a simple choice, really. Get busy living or get busy dying.

This isn’t going to be an easy battle. These doubts around dating are old and entrenched. They’re reinforced by awful dating experiences and by bad church teachings. I’m not saying I’m going to emerge from this lenten season with a girlfriend, but I am saying that I am NOT going to let fear get in the way of trying. It’s me versus Clubber Lang and I’ve gotten my ass beat by him before, but that was then and this is the rematch.

Doubt is staring me down, saying, “I’m gonna bust you up.”

And I’m saying, “go for it.”


Who knows what this unexpected, unconventional lenten journey will bring. Worst case scenario, I go out on a bunch of dates with some really great women and none of these encounters blossom into a full blown relationship. In the mean time, I get to practice my swagga and gain some new confidence.

Best case scenario…

Well, let’s not get too ahead of ourselves.


5 thoughts on “381. an unexpected (lenten) journey

  1. Pingback: 380. Bob redux (part 2) | Flavor and Illumination

  2. I like the cool red “rocky” shirt I am wearing in that gif.

    Seriously though, yes. Good post. Go for it. Truth is where it’s at, and those things that you’ve been telling yourself all these years are plainly untrue. So ditch ’em. For reals.

    /pep talk

  3. Pingback: 382. what a guy wants | Flavor and Illumination

  4. Pingback: Giving Up Singleness? | LoneTomato808's Blog

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