In the halcyon pre-COVID era — which was either a generation ago, or last year, as time’s dissolved into a hazy suspension of eternity and ephemera — I’d go on just-shy-of-romantic friend dates with a local interior designer.

We’d dress up, meet in dimly-lit haunts for luxury cocktails or artfully-crafted bites, and wax poetic for three hours about the mysteries of the cosmos, spin elliptical yarns about our impossible pasts, or present elaborate dissertations on social constructs like dating and marriage. Or, rather, I would. She’d laugh and listen, enraptured, her Mediterranean sea-foam eyes glistening in the candlelight. She called one such encounter, “the best date since I’ve been in Austin.”

On our fourth or fifth such summit, I leaned in to kiss her. She reciprocated. We made out, often, for the next hour or so — my cheesy smile irrepressibly escaping me into the ether. We kissed goodnight. I glowed all the way home.

The following morning, I woke up to a text message saying, in no uncertain terms: “I did not want to kiss you last night. I do not like you in that way. I’m okay with being friends with you, but we can’t do that again.”

I sat on my couch, mouth agape and woozy from last night’s whiskeys, stunned. Did I misinterpret her signals? Was she really not feeling me? Shit. I profusely apologized, and we eventually got back together to do it again … minus the awkward attempts at kissing.

Starting last September, I was mostly out of town, and we hadn’t had a chance to connect. We finally reconvened in February, at an Italian restaurant we’d visited before and both adore.

As we caught up, I confessed I’d come down with a bit of burnout-sparked melancholia. We made — if not small talk, then medium talk, as a reasonable amount of wine flowed, and we passed our dishes back and forth. I wasn’t at my peak, and so my default when I’m not firing on all cylinders is just to ask carefully considered questions to get the other person to open up. She did.

When we left the restaurant — me to go back home and nap, her to attend an exclusive house party at some billionaire’s mansion — she told me, “You know what? I think that was the best conversation we’ve ever had.”

Origin Story

In case you’re new here — in which case, welcome! — my history goes a little something like this: I am, physically, as unmemorable as it gets. I’m 5’7″, 175 pounds, healthy-but-not-fit, brown hair, brown eyes, olive skin, balding-but-not-bald, and I dress almost entirely in zip-up hoodies, soft v-neck tees, jeans, Pumas and beanie caps. I’m not unattractive; I’m just not gonna break your neck as I walk by.

I grew up kinda quiet and polite. Yes ma’am, yes sir. I’m pretty sensitive, although I wouldn’t quite say I’m an empath. Just … I have the capacity to feel emotions fiercely — mine and others’ — particularly joy, and express them elegantly.

I have a long fuse. Anger, for me, is exceedingly rare … and I iterate through it quickly. I’m pretty happy 85% of the time and moderately depressed the other 15% — usually in the months following a major life change.

In short: I wouldn’t be someone you’d approach on the street or give a second look to at your neighborhood watering hole. I’m unassuming and unremarkable. I can occasionally go days without speaking a word to anyone. I often got, and still get, confused for other people.

A Lifetime of Differentiation

To break through my default state of anonymity, I knew I had to add maximum value to every social interaction. I knew I had to cultivate an unreasonable amount of charisma. I poured myself into learning new skills. I said yes to every new opportunity — professional, personal, or otherwise. I got good at writing and storytelling. I started taking big, enormous risks. I lived hard. I — as they say in the movies — “done seen some things.”

As I experienced more, the content got better, and my confidence increased. I became differentiated to the point of being almost singular. That’s not my delusions of grandeur talking. That’s just facts. How many marathon-running, yarn-spinning, activist-humanitarian, globe-trekking, essay-writing singer-songwriters do you know?

My polymath tendencies and over-the-top personality weren’t really an attempt at world domination, they were a defense mechanism against being seen as disposable or interchangeable for a better, brighter, shinier model. I had to be the life of the party to justify my invitation. I had to stand out, stand apart, and be the most and best, or else I would be nothing.

I set unreasonably high standards for myself — to, in the immortal words of the Pokemon theme song, “be the very best like no one ever was”— and attributed people’s lack of interest in me as evidence that I was, in fact, not enough … and I’d convince myself I just needed to try harder and add more value.

In sum: I had to be extra just to be enough. In retrospect, this was an erroneous course.

What People Really Want

In my examinations of and explorations into the human condition, I find people generally want the same things in life: satisfaction and belonging. Most people generally just want to feel like to feel good about themselves, and feel like they’re seen, safe, and supported. Everything else — health, joy, peace, love, security, equality, purpose, truth, freedom—ladders up, in some way, to satisfaction and belonging.

That sounds so … dull and elemental, doesn’t it? Like, satisfaction? Belonging? What about the grand cosmic quest for meaning and legacy and an unshakable knowledge that life itself isn’t just one big random accident, in which humans are infinitesimal expressions of a boundless universe, created by infinite circumstantial examples of physics, math, chemistry, biology, and astronomy? That’s extra. Come on, now. When I write it like that, it sounds preposterous and comically grandiose.

We find satisfaction and belonging in others when we feel mostly safe, and occasionally thrilled by, the people we surround ourselves with. If you think of all great relationships — friendships, working relationships, domestic partnerships, life-long loves — we feel safe around them, and occasionally thrilled to be in their company.

If we think of safety like fried chicken (or, insert your favorite comfort food here) — something warm, unobtrusive, filling, and savory — then we can think of thrill as the spice that accents the dish. Not enough spice? Serviceable, but bland. Too much spice? The fuck am I gonna put that ghost-pepper wing in my mouth for? Who am I, a masochist? That’s not safe! Is there a waiver I can sign?

Satisfaction and belonging. Safety with a little bit of spice. That’s all we’re after. Everything else is just too much. Compulsive polymathy and over-the-top charisma? That’s too spicy. That’s too extra. It ain’t safe no mo’.

The Key to Lasting Captivation

I’m not saying don’t be interesting. Please, be interesting. Just … not too interesting. Not too quickly. That shit’s overwhelming. That’s dumping a whole basket of scotch bonnets in your fried chicken batter. Thrilling for some, but unpalatable for most. You don’t need all that heat. You just want that good slow burn and a savory, complex flavor profile.

As Christie Alex Costello, MBA once told me over text, “Don’t give it all away … just drop your line in the water. Don’t force the fish.” (A fucking fishing metaphor for dating … where have I heard this before …)

This isn’t just for dating, either. (Although it’s definitely for dating.) This is when trying to work any room — from the boardroom to the bedroom, from the bar to the park, from the dinner party to the fundraising gala. You don’t have to be anything more than memorable.

Longer-term, all you have to do is meet expectations. Show up when you say you will. Be consistent. Say what you mean, and do what you say. Make, and keep, promises. Extra will never be enough. Enough is always enough.

A seminal 2014 column in The Atlantic, “Always Make Promises,” summed it up thusly:

Imagine you’re a kid with a cookie and a friend who has no cookie. What happens if you eat it all? Your friend will be upset. What happens if you give all of it away? Your friend will like you a lot. What if you give away half the cookie? Your friend will be just about as happy with you as if you gave him the whole thing. His satisfaction is a pretty flat line if you give anything more than half of the cookie. People judge actions that are on the selfish side of fairness. Maybe because we denigrate do-gooders, or because we’re skeptical of too much selflessness, the research shows that, as Epley put it, “It just doesn’t get any better than giving half of the cookie.”

People feel safe when they can trust you. When they can rely on you, depend on you, and feel like they’re getting a consistent experience out of you — day after day, year after year. That’s how you keep people captivated.

People feel satisfied — and like they belong — when they’re able to share equally when they feel their emotional vulnerabilities will be taken care of, that they can laugh easily, and that there’s a certain amount of genuine reciprocation of interest and bidirectional respect and curiosity.

When I asked my friend what made our most recent friend date — in February, our last before a pandemic placed all future dinner plans on hold indefinitely — the best conversation we’d ever had, she elaborated:

“Because you were different. You were … normal. Raw. Yourself. Relaxed. You asked questions and didn’t go off on wild tangents. I mean, yes, I love learning things when I’m with you and I think you’re an amazing storyteller and incredibly entertaining, but sometimes I don’t want to unravel the mysteries of the universe when I’m with you. Sometimes, I just want to talk and enjoy an evening out.”

“Living up to a social contract is inordinately valuable, and there’s no pressure to exceed it.” — James Hamblin, “Always Make Promises,” The Atlantic, 2014

Extra Is Never Enough

Again, in the pre-COVID-era (last year? last decade? who knows?!), I’d gotten close with a woman who lives in New York. The relationship started — as they all seemed to with me — with me telling long-winded stories that invoked attachment theory, hyper-modernism, industrial agriculture, monetary policy, socioeconomic justice and jazz-like riffs about Tinder, masculinity, “the soulmate window,” and on, and on.

“This is like listening to my favorite podcast,” she told me, as she would drift off to sleep in the midst of my Kafkaesque ramblings.

Yet, we’d hit a bump in the road, and she voiced concern, talking about how she didn’t feel there was enough space for her. I totally got it.

“Mannnnn …” I told her, “I thought about that a lot.” And then I continued, “I’d be like …. ‘There’s no way she wants to hear all this. I’m talking way, way, way too much.’ And I would ask if I could stop, and you would say, ‘Please keep talking.’ So I just kept at it, because I thought that’s what you wanted.”

She replied, “And I just kept listening because I thought that’s what you wanted.”

Boom. Problem solved. And another very important lesson was learned: Sometimes, when you think someone enjoys you when you’re being extra, they’re doing it because they think you enjoy you when you’re being extra. They’re not enraptured in your immersive discourse. They’re just being quiet and polite.

You do not need to be the best date someone’s ever had. You do not need to be someone’s favorite podcast. You do not need to be the brighest star in the sky. You do not need to be the life of the party. None of that is captivating … it’s exhausting. It’s too spicy. People can’t trust it and they won’t feel safe.

If you truly want to captivate someone, just be present for them. Show up. Be consistent. Be vulnerable. Be comfortable. Be curious. Ask questions. Remember conversations from before. That’s all … and that’s enough. 

Everything additional is just that: extra.

Oh, and, if you have a cookie … maybe give ’em half. I hear it doesn’t get any better than that.

This article was brought to you by PS I Love You. Relationships Now.