The Wimpy Texter*


Kenneth and I, circa March 2007, when we started dating.

I discovered a secret. Shame dissipates when you throw the vile details of the things that torture you out into the open. Like a fish you’ve finally caught, floundering on the ground at the end of a line, gasping for air, its fate uncertain. Just put it right out in the open for everyone to see. Transparency. There is something you can trust about transparency. The vulnerability. It’s like a gateway for us to connect with each other, a reminder that we are all human.

When I’m transparent about the details of my awful experience with grief and starting over, I feel better. Better in the sense that a load has been lifted off my shoulders. It’s hard work to carry around shame.

Today, I’m going to give you my gory, boring details about another little baby step I’ve had to take. I hope you don’t fall asleep. It’s actually not that interesting. It’s even kind of stupid.

I feel a lot of shame about starting over in the relationship department. I’m basically a Buddhist-atheist with the family values of a textbook Catholic, or maybe a Mormon. I thought I’d be married until the very end, through rain storms and sunshine, with a large family. A gaggle of kids. That’s what I wanted. I definitely wasn’t supposed to become a 34 year old widow with three young children. I most definitely wasn’t supposed to have to try to date again in my lifetime, at least not until I was at least in my 60s. I knew I’d have to eventually venture into that murky water since my husband was much older than me. But not anytime soon. Not soon enough to even begin thinking about. Someday. It’s always someday.

My husband has been dead for almost 15 months. The idea of dating again terrifies me, but buried beneath all of the angsty emotions is a tiny bit of excitement for what might happen. I’ve never believed in having only one great love. The potential for meeting somebody new, somebody maybe even completely different from anything I’ve experienced before, is the kind of potential that gives me something to look forward to in a life that can feel overwhelming and dismally unfair.

I don’t want to be alone forever. I don’t think most humans really want to be alone, unless it is a better alternative to their other options. I didn’t choose to be alone. It was forced on me. So, in my mind, I have to force my way out. Somehow.

I’m not 24 anymore, which is the last time I had to bother with dating. And let’s be honest. That kind of changes the terms of the game. I know. It could be worse. I could be 54 and starting over. I could have an infinite number of odds stacked against me that would make this worse, but this is MY worst.

My first attempt at doing “this” again was an abysmal waste of time.

This is the story. I’m warning you: it’s embarrassingly boring and uneventful.

My friends, an anonymous husband and wife team, with all of the best intentions in the world (I think…?), thought it would be a good idea to attempt to set me up. My sister informed me that this is an effective way of meeting people. Social circles. Since I don’t seem to be procuring any better strategies, I figured I might as well go with the flow.

The man in question was friends with them. A widower. My first thought was: great, we can reside on the island of the misfits together. How pathetic and sad.

It was 8AM and I was still in bed on my last week in Europe (Copenhagen, to be exact), when I received a text informing me of this potential match. The text read like a mini novel first thing in the morning and included a picture of the man and his daughter. I rubbed my eyes, wondering why my friend would randomly text me a picture of a man. It made sense the further I read. This is _____. He’s so great. Blah blah. I gave him your number. (I’m paraphrasing here.) And some stuff in the middle, sounding like a personal ad written by an optimistic and well-meaning friend.

I literally replied “OMG” and laughed out loud. I didn’t know what else to say, or think. I wasn’t offended that my phone number was given out. I just never considered it. I was finally in a place where I had convinced myself that I was okay with being alone (for now) and would just stay busy focusing on my projects. Workaholic mode, I convinced myself. Better than sad mode. Better than licking my wounds mode. Workaholic is a respectable alternative to lonely, right?

After finally reaching this point of zen-hood after many agonizing months of trying to reconcile the emptiness inside of me, the idea of meeting somebody was unexpected.

I didn’t say yes. I didn’t say no. I decided to just wait and see what would happen.

So I waited to be contacted.

And waited.

And waited.

It kind of bothered the feminist in me. Why did I have to wait like a helpless animal ready to be preyed on? It didn’t seem very 21st century. But what did I know?

I waited some more.

Now I was wondering if there was something wrong with me before I even had a chance to speak to or meet this man. Did I seriously strike out before I even went up to bat? Before I even picked up the bat?

Was this my grand re-entry into dating?

There I was: smack in the middle of familiar memories of singlehood. The uncertainty of meeting somebody new. Worrying about everything they could possibly hate about me. Feeling inadequate. Wondering if I would ever even meet someone. Maybe I’d end up like my Great-Aunt Victoria, eternally single, collecting useless crap in suitcases every time she visited from overseas and scaring the children.

I was stuck in a pit of self-doubt. It had been so many years since I had to dwell in these swamps. I hated it then, and I hate it now. When I met Kenneth, it was so easy. He side-swiped me before I knew what was happening. I hadn’t thought twice about him. He was the teacher in the classroom next door to mine. He wasn’t even an option in my mind. And then one day he decided to win me over, and he did, before I had time to think about it. I liked that. There was no dwelling on not being good enough. There was just one day a man who thought I was the best thing he had ever seen and met. That’s what I want. Not these yucky negative thoughts. Something easy. Why can’t one thing be easy in my life????????

After waiting and waiting wondering what I would say if/when this man would finally call, we discovered that he was given the wrong phone number, which explained why I wasn’t contacted.

Thanks, Friends. Way to increase the awkwardness.

In my mind I thought this was a sign. A really bad sign. This couldn’t turn out well.

But I was going to shut up. See how it went. I had to try, my friends told me. I knew I had to try, but it didn’t mean I liked it. But try I would.

Correct number was given, and I waited a few more days.

Finally, a text, not a call.

Okay. Text messaging. That’s what they do today, right? I consulted my 18 year old friends just to be sure. Yes, they confirmed. It’s all about texting. Nobody calls. I just wanted reassurance that this wasn’t weird. I can text. It’s not what I experienced the last time I dated, but you know. I’m okay with embracing changing times if it leads to something interesting.

Conflicting schedules meant there were no phone calls or meet-ups for the first several weeks. I was out of town. He was out of town. I was out of town. You know. These are apparently the problems of grown ups when they try to meet new people. It certainly wasn’t a problem for early-20s me.

I’m an impatient person. I already know this about myself. That’s why being side-swiped works much better for a brat like me. Turns out side-swiped isn’t on a menu for take-out, so I have to get what I get. I’ve been trying to have an open mind about what “older” dating looks like. Or let’s not even make it that serious. How about just “meeting people.” I’m just willing to meet people. No high stakes anything. Just meeting. Still, meeting people looks a lot different once you’re out of your twenties.

Meeting people when you have children.

Meeting people when you have a career.

Meeting people when you have a 9PM bedtime.

Meeting people when you have a hell of a lot more at stake than when you were 24 years old.

Meeting people when you have had your heart broken into tiny shards in the worst possible way.

Meeting people when you feel like a castaway.

I know that I need to have a sense of humor. I know that I need to be patient. I know I need an open-mind. I know I need to have flexible expectations. I know, I know, I know.

But in reality, it’s only been 15 months since my husband died. I’m still angry as hell at him for leaving me behind. Why would anyone want to stop wearing their yoga pants and start shaving their legs again on a regular basis? I want to file a grievance. How dare he make me start using facial creams and caring about my thigh gap. I feel like he would be laughing at me, somewhere, somehow, as I bungle my way through this crap. I know he’d be very amused. And very sorry, so that makes me a little less angry.

I’m not 24 anymore. It’s hard to forget that, even though I know I have to. I already know what I have to do, but it’s always easier said than done. And this still feels so patently unfair.

I can see the wrinkles on my face.

I’m definitely more cynical. Guys like stupid 18 year olds. 18 year olds don’t ask questions. I should know. I was that 18 year old before.

My body has changed. I could spend time thinking about how it’s changed for the better, like how I’m thinner than I was at 24 and more fit, but nah. That ruins the pity party.

I drive an f-ing minivan. How am I supposed to “meet” someone when I pull up in my goddamn minivan? (I am so angry at my husband for this one. He’s the one who wanted the minivan!!!)

I have three young children. THREE. I might as well have herpes all over my lips to deter potential man friends. I mean, seriously. I waited my entire life to be a mother and have a family, even opting to not go to law school because I didn’t think the career would be conducive to the vision I had in my mind of the kind of mother I wanted to be. But now, single and widowed, being a mother sometimes feels like the bane of my existence, and I feel horribly guilty for feeling this way. It just wasn’t supposed to be this way. I was supposed to be with my husband, marveling together over the way Peter strings sentences together now, or how cute Ethan looks with his missing teeth, or the way Ellie changes outfits 50x/day. This was a team sport. This wasn’t supposed to be me playing all positions in the infield and outfield.

It’s not just about missing my husband. That has come to be the easiest part of all of this. The part I’m having the most difficulty with is the ruination of my life expectations and plans. I’m having trouble believing that I won’t be lonely forever.

Okay, so I go along with this texting guy. He is completely boring at first. The conversation is more polite than how I would talk to the parents of my students. I mean, totally generic. But that’s okay. My husband used to be really into the psychology of dating, and he taught me all about how hard it is for men to be their true selves around women. I could put up with some bungling, and maybe help ease more personality out of the conversation. Besides, I could empathize with him. He lost his wife. I get it. This sucks for everyone. He gets a couple free cards.

Older-Meeting-People-Me has convinced herself that she needs to practice patience, so I complain to my friend about how boring it is but I continue to go along with the texts. She assures me how wonderful he is. I wonder if I’m scaring him off, but he appears to keep texting back, so who knows. I hate how I went from confident wife to puddle of uncertainty literally overnight. Who am I? This is not who I am, and yet the vulnerability of the situation is enough to unravel the person I had spent a lifetime building. I have to find the lost me, somehow. I know she still exists inside of me. Somewhere.

After a while, after what feels like pulling some conversational teeth, real conversation begins to happen. I decide that I like him. Yes, this could have potential. He’s different than what I thought I’d go for. But I like him. I’m a great judge of character; I just need to meet him to confirm with my trusty gut feeling. I am cautiously optimistic.

Several late nights of texting occur. Interesting conversations. Now it was messing with my rigid, workaholic schedule. But…I could make exceptions, I decided. I needed to get into this “meeting people” game. I couldn’t jump into the game by being rigid and telling guys that it’s past my bedtime. I needed to be open-minded. Flexible. Patient. Go with the flow. Everything I’m not by nature, but I would force it. I don’t have any other options, I think.

This goes on through a couple of (separate) vacations. I’m starting to wonder if I’ve bored him with my conversation skills (but I mean, the nerve if that’s true, because he bored me first!).

I kept wondering if he’s going to suggest meeting.




In the beginning, he’d text these ridiculously corny, generic things. Like…

“Good morning! I hope you have a great day!”

First of all, stop with the exclamation points. It’s like you’re laughing at your own jokes. Just stop. Secondly, I just “met” you. Let’s slow down on the niceties. Why don’t you tell me your zodiac sign first, and maybe a little something from your resume? And if I like you, you can tell me good morning and hopefully bring a cup of coffee with it.

Maybe I just suck at being a human being. It’s entirely possible.

The evenings got even cornier. The same text, daily, saying something about good night, sleep well, have sweet dreams.

*rolls eyes*

And yet, after a while, this ridiculousness started to grow on me. I kind of liked it. I’ll admit that I don’t always know what’s good for me, so I try to be open-minded so I can participate in unexpected goodness. It was these stupid little greetings, or lack thereof, that alerted me that something was wrong. They stopped coming.

Did that mean something? Why aren’t I getting these corny messages anymore?

That’s it, I thought. I finally scared him off. It’s done. I knew from the beginning this was doomed.

Why did I care? I mean, this dude goes to mass every Sunday. An altar boy. Practically a Boy Scout. There is no logical reason why I should care if he texts me or not. I’M NOT SUPPOSED TO CARE.

As it turns out, I’m not completely a cold-hearted robot, and I find myself caring more than I’m comfortable with, even though I’ve never even met this dude. And it’s kind of disappointing, because I actually liked him. You know, as much as you can like somebody from text messages. It was entirely possible that his pheromones would have been a dealbreaker. But that’s still a big question mark.

I guess I could have been a feminist about all of this and escalated the situation myself instead of waiting around for him to do it. But…no. I decided to go ahead and deem this a man’s job. I’m not going to do it. We women deal with a lifetime of having a vagina. You, Men, have to deal with initiating and escalating relationships. Sorry.

Instead of being proactive, I decided to dwell in chick logic and behavior, which includes: putting oneself under a microscope and identifying every possible flaw, whining about it, complaining about your dismal options, moping about your state of affairs, and thoroughly envisioning every detail of the convent you will soon reside in when you begin your life of exile as a nun.

That was definitely the route I was going to take. A glutton for misery. I could just beat myself over the head with all of the reasons I could invent about why somebody would never, ever want to actually call me and meet me in person. I’ve got this long, long, nasty list of why I must be untouchably horrid. Don’t even mention any of my positive attributes. It would ruin the mood.

The swamp. I was sticky with its grossness, drowning in the quicksand of self-loathing. I must be too fat. Too ugly. Too many kids. Too boring. Too mean. Too everything horrible under the sun for anybody to possibly like.

Why the hell didn’t I just stick to Workaholic Mode??

Finally, the writing was on the wall. This wasn’t going anywhere with Wimpy Texter. I literally wasted a month of my time. I let my guard down. Just when I was in a blissfully happy stage, content in workaholic mode and happy to focus exclusively on my goals and my children, I decided to go along with someone giving out my phone number.

And I couldn’t even make it to the phone call stage. Seriously, it can’t get worse than that, right?

It’s kind of funny. And kind of sad.

Basically, this is all proof that I suck at all of this and will die a nun. And that my friends should never, ever attempt to set me up again, unless they are giving me a referral to a comfortable convent for me to begin my life as a nun.

Goddamn Kenneth. He did this to me. This is all because of him. I could be in yoga pants and messy hair and not caring at all what I look like, and instead, I’ve been thrust into this alternate universe of meeting people at a time when most people are married with kids or getting divorced and going to therapy. Basically, a time in my life when the pool of what I would consider to be suitable potential candidates is very, very shallow and tiny. I need a Plan B, but not a Plan Desperation. I’d rather be alone than go with Plan Desperation.

So that’s my story. Embarrassingly boring, and I’m back to the drawing board. I will figure this out (and grow thicker skin). I hope.

I’m not happy about the time that I wasted on this, but at least I got some essay fodder out of it. Thanks, Wimpy Texter. I hope we can sustain eye contact when we meet again at our friend’s annual holiday party, perhaps standing over the lemon cookies, when we happen to both look up at the same time and notice each other across the table. Maybe we’ll divert our eyes and pretend not to know who the other person is.

Or maybe I’ll just stay home, “sick.” After all, I’m really just a big baby under my tough exterior.

*I don’t really think he’s wimpy. He probably has excellent reasons to stay away from me. Who knows. I’ve never actually talked to him.


  1. Never boreing! Always insightful funny and sad because you’re telling a real life story of grief and triumph.


  2. Hi Theresa. I’ve read all of your blogposts after I found you on tinybuddha, and think you are such an inspiration in so many ways. I’ve especially admired your feminist message (particularly to your students), and how it is so important to stay true to yourself and your identity as a woman and individual, even after becoming a wife and a mom. (For me, a (happily) single 27 year old, this is of course far from my reality at the moment, but I found your thoughts on this so inspirational). That is why I am rather taken aback – and fascinated – by your thoughts on dating and dealing with this situation in particular.

    I just don’t understand why a strong, independent, smart, and attrative woman like you, would give this man (and stranger) the power to spiral you into self-doubt and restless waiting for so long, because of some notion that “men, have to deal with initiating and escalating relationships”. To me this is so contradictory to many of your other thoughts on being a woman.

    I understand that you are in an extremely vulnerable situation and that these gender based stereotypes of being pursued by a man might be more deeply rooted in the US (I’m from Norway), but as you venture into the dating waters again, I hope that you carry with you what I see so clearly; that any man who ends up with you (or even just meets you for a coffee) is extremely lucky, and if they don’t see that – figure it out as soon as possible (e.g. shut down bullshit like this) and carry onward.

    Wishing you all the best, always looking forward to your writings.


    1. Hi Line, I really appreciate your comment. Thanks for taking the time to leave one. I think being a strong female is not about lacking feelings of self-doubt. Those are what make us human and not robots. I think it’s more about not getting stuck in the feelings. While I wrote an essay about the couple of days of frustration I had over this issue, I most definitely have moved past it. 🙂 Feel it, then let it go. That’s my motto.


      1. Thank you so much for your kind reply to my (in hindsight somewhat naive) comment TEresa***. You are of course perfectly right, and I certainly feel and (try to) let go of self-doubt all the time. x


  3. Hi Teresa,

    Not boring at all. I know why you started with that, you think ‘well if they think it’s boring, at least I already predicted that’, as if that kind of cancels it out straight away if somebody does find it boring, which they wouldn’t.

    I’m just wondering, did you consider that this guy was also feeling all the things you were feeling? Maybe he was also having a crisis of self-confidence and thinking that he wasn’t good enough. Maybe he is still feeling all the raw emotions that you are feeling, and he is afraid of getting hurt, of being rejected, so he didn’t want to take too much of a risk and put himself more forward in case you recoiled and thought ‘what a weirdo’ or ‘gosh he’s too forward’. Maybe he was worried that you would stop replying, which would reinforce any feelings of ‘I’m boring’ that he might have had.

    I think possibly you both missed a chance for healing, you have both been afflicted by the same fate. I’m not saying that you could both wallow in some pity party together, but I think you could have had a deeper connection with this guy because at least he knows what you are going through.

    Speaking from a man’s perspective (we are unfortunately very shallow creatures), we need to feel that a girl is interested before we proceed further, there needs to be some kind of flirtation, which is kind of like a positive reinforcer, so we continue to indulge in ‘the chase’. If the scent goes cold, we give up. Yes we are basic creatures deep down, we just have a neo-cortex.

    I know it’s easy for me to type this drivel and post it but try to think ‘I’ll give this a go, if it works out, great, if not, also great, so what’. I don’t think there’s any need to wholeheartedly put your entire soul into it.


  4. Fantastic insight into what it means to be human. There’s a lot of fight in this dog. PLEASE START YOUR POLITICAL CAREER. Are exclamation points really that bad?


  5. Hello Theresa,

    I can see why Mr. Shimogawa “side-swiped” you as you had mentioned. The thing is there was a moment where you question your ability to be human. This is where I believe you are above and beyond the ones who don’t have the thoughts that you have had. You allow yourself to feel and by doing this you are inevitably learning from everything that you feel. Those who choose to opt out on the feelings game are static human beings. (Of course no offense to those who don’t feel). I admire your resilience. I know it isn’t much… but I have this gut feeling you will get what you want. You WILL have to be flexible just as you mentioned, but your mind is so unbelievably beautiful you will never have to bend over backwards. Then again, what do I know? Either way, don’t stop writing, you have definitely given me strength, and I am guilty of spending my whole morning dedicated to your blog. Sending all the love in the world to you.


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