Addison Walker

It’s 1 a.m., and instead of sleeping, you’re at a cocktail bar sitting with an old British friend talking about your childhood, exes, and your existential crisis over a mezcal negroni. Somehow, this has become the new definition of intimacy, confessing everything to someone we already know won’t be around for the ending.

Too specific? Yeah, this was how I spent my Thursday night.

Somehow, casual meetups have turned into late-night therapy sessions, and nowadays we seem to measure connection by how many secrets we can tell each other by morning. But are these conversations genuine intimacy or just emotional oversharing dressed up with clever banter and a bar tab?

Photo courtesy of Gabby Lalonde

I realized this after meeting with someone I hadn’t seen in a year (the British guy of course). I thought I had tucked him neatly into the “past flings” file of my brain, but within minutes we were back in our old rhythm. Exchanging stories about work, relationships, travel and everything in between. It was comfortable and dare I say, intoxicating. However, by the time I got home, I found myself wondering: were we building intimacy, or just falling back into our old habit of filling the night with confessions because we didn’t know what else to do?

The line between intimacy and oversharing is thin. Authentic intimacy takes time, it’s earned slowly, like trust. Oversharing, on the other hand, can be impulsive, like listing every dessert on the menu before you even remember if they have a sweet tooth. (Thankfully he did, we had crème brulé.)

And it feels good. Those late-night conversations release oxytocin, the same hormone that is released during a hug or a kiss. It fires into your brain like an emotional shot of espresso. No wonder we keep coming back, even when the relationship itself is undefined.

But oversharing is not the same as getting to know someone. Getting to know someone is mutual and gradual, sharing interests, opinions, dreams, while oversharing drops heavy truths too early on. It can turn a night of “fun catching up” into an accidental therapy session.

The difference is timing, intent, and reciprocity. Intimacy builds connection while oversharing seeks relief. And while intimacy is shared, oversharing can feel one-sided.

The danger is that vulnerability can trick us into thinking we’re closer than we are. Just because someone lets you cry on their shoulder does not mean they signed up to hold your heart.

Part of this is because our generation is emotionally fluent in a way our parents weren’t, we know our love languages, attachment styles and emotional habits. We care about mental health, and that’s a good thing. But we also seem to be lonelier. Many of us are delaying long-term relationships and committed dating. We let our friends, flings and hook-ups shoulder the emotional labor.

The result? Nights that feel like a mix of therapy, romance and a TED Talk. We leave feeling seen in the moment, but oddly hollow by morning.

The answer isn’t to avoid these kinds of talks altogether. Being vulnerable is beautiful, but maybe we should think about what we’re actually hoping to get out of it. Are we trying to figure things out or for someone to hold our feelings for a night so we can feel lighter?

After my Thursday night, I felt both anchored and adrift. Maybe these late-night sessions are meant to be checkpoints rather than destinations. They don’t always mean love and intimacy. Sometimes, they just show us where we need to grow.