As someone who makes a living staring at a blinking cursor that seems to always be a step ahead of me, I often find myself retreating to—if you’ll permit me saying so, here on this website—the analog version of Microsoft Word. Not to romanticize it, but writing is an intimate act, and that aspect is often overlooked as digitization marches on. (Well, except in Milan. The folks at Moleskineseem to get it.)

Believe it or not, technology companies seem to be aware of the problem. Microsoft, among others, is putting a lot of effort into replicating the familiarity of pen and paper on a layer of pixels below a slab of glass. It’s one reason why the company touted the Surface Pen as a primary selling point for its Surface Pro 3 tablet. As you may recall from an earlier column, I was veryimpressed with how it performed, and as I went from meeting to meeting with it during a trip to Japan, people continued to approach me and ask: “What stylus is that?” (Which was often followed by: “Does it work with the iPad?”)

The Surface Pen does not work with an iPad, of course—its proprietary software is Microsoft-compatible only. But the inquiries set me on a search to find an iPad stylus that could replicate the experience of the Surface Pen and, by extension, the conventional pencil or pen.

My search began with Pencil from FiftyThree ($60 and up). Its chiseled form is reminiscent of a carpenter’s pencil, and its walnut or graphite housing underscores the reference. On the business end you’ll find a soft rubber tip designed to glide across an iPad display; the butt of the tool offers another contact point that’s meant to duplicate an eraser. Thanks to a Bluetooth 4.0 sensor, the implement can detect tip pressure (which, through software, translates to line thickness), determine when the eraser end is in use, and eliminate any errant doodling when you rest your palm on the screen.

Writing with Pencil, it was apparent that I was using a digital tool. Instead of concentrating on what I was writing, I constantly found myself focusing on what I was writing with. How I positioned the tip of the stylus was a persistent thought because its soft material made the contact point change in shape as I wrote with it. My letters would blend together unnecessarily, not unlike the stereotype of a physician’s freehand, leaving me to decipher my own transcribed thoughts. Pencil makes for a superb sketching tool, but as a writing implement it left me wanting.

The Cosmonaut by Studio Neat ($25) was recommended to me by a reader. This stylus was thick like the Pencil but was cylindrical, designed to replicate the feel of a dry erase marker. The Cosmonaut is far simpler than its peers because it lacks internal electronics and dedicated software, instead relying on a device’s capacitive screen for interaction. The rubber tip of the stylus is firm and made for a consistent contact point on the iPad’s screen. Despite the tool’s girth, I felt like I had more control over my handwriting than the Pencil—I could indeed read my own handwriting. Unfortunately, it stops there: because the stylus lacks its own software, it offers little in the way of pressure detection or quick-erase smarts.

Is simple better for a stylus? I walked out of a Best Buy with a slim model made by Targus ($9) to find out. The implement has a soft rubber nib on one end and most closely resembles the shape and size of a traditional pen. Like the Cosmonaut, the Targus stylus lacks internal components or accompanying software. Unlike the Cosmonaut (but quite like the Pencil), it was a complete distraction during use. It quickly became clear to me that this stylus was better suited to acute tasks, such as selecting icons or buttons in an interface, rather than free-form writing.

To the other end of the price spectrum, then. The Adonit Jot Touch ($120) was by far the most expensive stylus I tested, and like most of the models I used, it had a thicker profile, akin to a full-size Sharpie (but with two buttons where your thumb might rest). Like the Pencil, the Jot Touch uses software to facilitate interaction with an iPad. The two buttons can be assigned actions, depending on your composition app of preference; during my testing, I set the bottom one as an “Undo” action and the top one as a “Redo.” (What can I say, I’m an indecisive writer.) Though the Jot Touch’s body is thicker than a traditional pen, its “Pixelpoint” tip isn’t, and I found it suitable for writing at length.

The world of styluses is surprisingly large, and I in no way claim to have tested every size, shape, or type available on the market. (In Best Buy alone, there was a four-foot section of them.) I evaluated the implements above on the advice of readers and personal research, using the Noteshelf app as my digital paper of choice. (Which, I should note, explicitly supports the Pencil and Jot Touch.)

After a week of staring at my embarrassing penmanship—at times laughing at the fact that it could actually get worse than what’s already become of it in this keyboard-first world we live in—I came to an obvious conclusion. The Jot Touch, with help from Noteshelf, is the iPad stylus that best replicates the pen and paper experience so many covet.

But a facsimile is not the real thing. If you’re looking for an intimate, creative, even romantic way to put pen to paper—well, you know what to do. Let the mind wander. Doodle in the margins. There’s a time to be efficient. This isn’t it.