Here’s a shortlist of the things I post about on the Internet on any given day of the week: the latest Rihanna remix, excerpts from interesting bits of writing around the Web, GIFs that made me crack up at my desk.

Digital Diary

One woman’s look at technology and life.

Here’s an even shorter list of the things I don’t post about online: death, or to be more specific, the recent death of my father.

Why is that? We know that the Internet loves a good death hoax (R.I.P. Boo) and has become the medium of choice for mourning the passing of a celebrity or famous figure. The night Steve Jobs died, for example, all of my feeds quickly transformed into a virtual wake, attended by thousands, flooded with fond words, video clips, tributes rendered in GIF and Photoshop, a loving remembrance created and shared by Mr. Jobs’s admirers in their native mediums. When Whitney Houston died suddenly, we gathered online, stunned, taking comfort in knowing that others just like us were struggling to make sense of the loss.

Eternal Flamexkcd Eternal Flame, a tribute to Steve Jobs.

As Rick Webb pointed out in a post on BetaBeat last year, the death of a public figure can bring out our oversharing tendencies in full force — often to other people’s discomfort.

“Many Americans believe strongly that grieving should be private or at least subdued,” he wrote. “We should be respectful of those who were closer and are in more pain than us. Social media throws a monkey wrench into this, and it can look ugly.”

However, when it comes to talking about death and grief in a non-abstract way — that is, when dealing with the loss of a family member, a partner or close friend — it gets much, much trickier. It doesn’t have an appropriate reaction face, a photo that you can reblog, a hashtag.

That’s because posting about a more personal loss makes people — both the poster and the readers — uncomfortable. It’s awkward enough to figure out whether to like, favorite or respond to tweets and status updates bemoaning a bad day, a breakup or a tragic news article. When it comes to death, it’s even harder. No one wants to see morbid thoughts and ruminations about death sandwiched between cheery updates about last night’s party and celebrity chatter.

The problem lies partially in the types of social sites and services that Internet entrepreneurs tend to build. There’s no Instagram to remember deceased loved ones, no Tumblr tag for death. There’s no GroupMe-like service for strangers to commiserate about sleepless nights and recurring nightmares. That shouldn’t be a surprise – what entrepreneur wants to pitch a venture capitalist on that app? What advertiser wants their products and brands sitting alongside a weepy comment or video about bereavement?

It’s endemic of a larger problem in the way we are encouraged – and discouraged – to express and present ourselves online. This is more than trying to decide how carefully polished you want your online image to be. It’s about the way social software is slyly engineered to get us to participate – we are encouraged to brag about our lives, and present ourselves as living our best lives each day and year. It’s not built to handle sadness or any deeper or more complex emotion than that. Which, in a way, makes sense — could a 140-character tweet ever fully convey the full extent of the emotion we’re trying to share? At best, we could look tasteless, thoughtless for taking to the Web instead of a more traditional outlet — like a phone call, e-mail or handwritten letter — to talk about tragedy and sympathy.

In other words, death is heavy; it’s a topic best reserved for offline conversations, in-the-flesh interactions with friends, therapists, counselors.

What the Web did have to offer me was outdated at best: archaic online forums and dusty chat boards. So in order to talk about grief, I have to do it the old-fashioned way — in a small, dimly lit office surrounded by other strangers plucked from the world. And as someone who lives out most of her life online and revels in the Web, I can tell you it feels very weird not to have an outlet for one of the biggest events of my life to date, right up there with graduating from college, getting jobs, moving to New York, all of which were shared, celebrated, praised on the Internet.

And not only does it feel weird: it gives the impression, at times mistaken, that all is well behind your screen. More than once, a friend remarked to me that it seemed things were fine based on my Instagram feed, tweets and Tumblr. That’s not their fault, far from it. It’s a perfectly adequate assumption to make — but one that reveals that we’re increasingly linking how we present ourselves online with how we are offline, even if we ourselves see the chasm between the two.

All of it has made me think: What is lost when we’re building a social Web that only caters to a select few options in the vast, vast catalog of human emotions?

Digital Diary is one woman’s look at technology and life.