I have a writing crush on a younger man

He’s funny, in his 30s, dad of two, shamelessly seeks approval, full of neuroses–just my type

I’m an

Alex Dobrenko`

fangirl.

I’m more than twice his age, so I could be his mother, or, if we timed it right, his grandmother. I’m waaay outside his target audience of cool Millennials and Gen Zers. And unlike Alex, who fearlessly spills his most self-deprecating thoughts, I second-guess myself, and then double-check with my editor¹, before revealing stuff that doesn’t make me look good (like ambivalent feelings about my dying parents). Despite all this, his writing connects with me strongly. He always makes me laugh! What’s the old saying? The best way to a woman’s heart is by making her laugh?

Alex’s absurd humor drives his riffs and rants in his bestselling newsletter, Both Are True, where he mines his life² as a young father, comedian, and TV actor. He often ends a post by unapologetically begging his reader to become a paying subscriber. (Alex, I paid!) He makes up his own spelling and writes in lowercase, which I used to find annoying but now I happily accept. And no matter how unexpectedly looney his topic, it’s not all quirks and humor—he always leans into vulnerability, revealing his underlying anxieties, fears, and neuroses.

Insecure and in good company

Even though it’s improbable that a 30-something guy and a 70-something grandmother could have something in common, I feel a strong kinship with Alex. His life is so very different from mine, yet it’s extremely relatable.

Foremost are his insecurities, of which there are many, and his ever-present need for approval and love. That resonates. That’s what’s inside my head too, now at age 73, back when I was in my 30s, and far earlier.

Actually, it’s been like that for me since I can remember. I was an only child for almost a decade and in those early years, all I wanted was to be accepted, to be liked, to fit in with the kids at school. But that never happened. I always felt like an outsider. In fact, my mother was responsible for my getting teased at school because she made me wear brown lace-up shoes that were NOT COOL. (She’d seen them in England, I think.) The other kids got to wear loafers. With pennies in them.

(Debbie) working on a puzzle at age 3… Am I doing it RIGHT? Am I good enough??

Even in my young married life as a 20-something, I still ached to GET IT RIGHT. I still yearned for approval and acceptance, maybe even accolades. Everyone else seemed to have figured things out… they all seemed popular and successful and well liked. Why not me? I’d graduated from Harvard, I’d married a doctor (although I didn’t really count that as a personal success), I’d gotten a masters degree in journalism and worked part-time for several newspapers as I began having babies, years before my peers… but it didn’t feel like ENOUGH. I still felt like I was behind (even though I was ahead in starting a family).

Peers in perfectionism

Here, maybe, is where I find the most overlap with Alex: even after getting accepted to an Ivy League school and graduating, I couldn’t rid myself of the endless internal rat race, couldn't stop myself from endless comparisons with my peers, and couldn't squelch the insatiable desire to be recognized as “successful.”

And then there is Alex’s desire to be perfect. Not just accepted or successful or cool—perfect.

I can feel this one in my core. I’m not sure if his family ever did this, but mine (aka my parents) made it clear, without saying it outright, that I wasn’t good enough. I don’t like to cook for and entertain large crowds, something my mother excelled at. I remember once she prepared a lobster dinner for 25 Japanese business associates of my father’s. This was on an island off the coast of Maine, with a rudimentary kitchen. For dessert she baked several of her famous Maine blueberry pies.

Amazing, right?! But overwhelming for me to even think about. How pitiful that I couldn’t do the same. Her judgment was clear: because I didn’t like to cook or create elaborate dinner parties, I was a failure. No chance at perfection there. I was smart, sure, but that wasn’t enough.

And then there’s Alex’s vulnerability

Despite all his insecurities and perfectionism, Alex is willing to be vulnerable. He’s willing, in his writing, to tell us the stuff that doesn’t necessarily make him look good or heroic or perfect but that is so honest. (Of course, he’s always very funny, which takes the edge off. I always giggle as I’m reading his essays.)

I have that same impulse, too. I want to be vulnerable, to tell readers about difficult, private things. The things I’m trying to work out in my head, the things that aren’t perfectly polished or resolved yet. If I dare admit it, I also try to be a little bit funny.

So, if there’s a unifying theme here that explains why I’m an Alex fangirl for life, despite the nearly 40-year age gap, it’s that we’re both trying to come to terms with who we are: our plaguing insecurities, our die-hard perfectionism, our unrelenting need for acceptance and love, for doing and being ENOUGH. And we’re willing to be vulnerable along the way.

If I could tell my writing crush one thing, it’s that I’m actually a bit envious of him. He’s got so many decades ahead of him to figure everything out, whereas I’m almost running out of time. I say that lightly but it’s bittersweet, as I look ahead 10 or 15 or 20 years from now. I may not be wearing those brown lace-up shoes anymore, but I have the same desire to be accepted.

Questions for readers

1. Do you think anxiety and insecurity are hard-wired into a person? No matter how hard I try, I can never seem to get rid of these demons. What about you?

2. If you could tell Alex Dobrenko one thing to make him feel better about himself, what would it be? Oh, and tell me that one thing too, while you’re at it!

3. ³

4. Do you have a crush on a Substack writer that you’re willing to divulge?

This post was first published on Dec.15, 2023.

1. Coincidentally, Erin Shetron, my editor, is one of Alex’s editors too.

2. A typical post from Alex is 2025 recap: what a year it’s been (ha ha published on Jan. 7, 2025). Or this one: can everyone kindly shut the fuck up about AI (includes his deliberately awkward, childish drawings) or this: parenting as improv: yes and yes and yes and (so endearing; about playing make-believe with his young son).

3. Leaving one question blank, like Alex does.