If I Ever Get a Dog, I'll Name It Rover: A Brief Introduction to Microsoft Bob

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March 1995. Although PCs had been around for many years at this point, less than 40% of households in the US owned one. Back then, people mostly associated PCs with being a machine used at work, not a thing you’d even need at home. They were complicated and… unfriendly.

Just a few months before the launch of the all-new Windows 95, Microsoft Bob was an attempt to create a user-friendly interface that runs on top of Windows to increase the popularity of PCs at home and show how valuable a PC might be for purposes other than business.

This interface provides a virtual home inside your computer, divided into multiple rooms resembling your house’s rooms. It’s designed to be intuitive and user-friendly, so you don’t need to know what a word processor is or how the applications are named — for example, just click on the pen and paper on your virtual desk and start writing a letter.

Introduction

When starting Microsoft Bob for the first time, you are greeted by Rover Retriever, the main mascot who will guide you through the program.

While the concept of having a virtual assistant as an integrated online help was new at the time, it would later gain popularity in the form of Clippit, the virtual assistant integrated into Microsoft Office.

After telling Rover a bit about yourself, setting a password for your account, and selecting a secret room only you have access to, you will enter your virtual home for the first time.

Then, Rover will take you on a tour of your new home so you know exactly where to find the different applications Microsoft Bob offers.

But wait, there are more objects on the screen, so what do they do? At first, I was worried I’d miss an application hiding behind one of the other objects.

However, the applications Rover mentioned are really the only ones included in Microsoft Bob. Everything else is cosmetic.

If you are unsure where your application objects are located, simply press the “F1” key to reveal all clickable hotspots.

Clicking on the books on the shelf, for example, reveals that they are purely decorative and don’t add any functionality. As you can see on the screenshot, you can replace the decorative objects, but more on that later.

The applications

Time to get some tasks done! Let’s have a look at the various applications bundled with Microsoft Bob.

• The Letter Writer
• The Calendar
• The Checkbook
• The Financial Guide
• The Household Manager
• E-Mail
• The Address Book
• GeoSafari

The Letter Writer

At first glance, the Letter Writer feels like a stripped-down version of Microsoft Word. When launching the application by clicking the “Pen & Paper” object, Rover will guide you through the steps for, well, writing a letter.

The application itself looks pretty straightforward and allows for many simple customizations. You can pick from various border styles, and premade cliparts for every occasion. It even includes the famous WordArt!

Letter Writer includes numerous templates. The pre-filled address book includes politicians, airlines, travel information agencies, departments for environmental concerns, newspapers, magazines, insurance companies, and others.

Yes, it is pretty versatile and a helpful start if you never used a word processor before. However, if you have some experience with Microsoft Word, it feels slow and tedious to use in comparison.

Will the next click allow me to start typing? Ah, no, another step in the assistant. No, I don’t want to pick an address from my address book because I don’t have any addresses yet. Yes, I’d like to have a nice picture in my letter. Sure, why not? Makes things a bit more personal. Thank you!

When starting the application, you can’t skip the assistant altogether. You have to click three times to leave it and being able to work.

Rover either didn’t mention it, or I missed it when skipping through the assistant: There’s no dedicated way to save the letter (file). Just exit Letter Writer, and it will be automatically saved for later use.

The Calendar

Clicking on the calendar on your virtual wall opens the Bob Calendar application.

Since the calendar offers fewer options than the Letter Writer, Rover is also much less intrusive. You can access all options right at the beginning and don’t have to click through a lengthy guide.

Add events, set reminders, and create your To-Do list — there’s not much to say about this application.

The Checkbook

The Checkbook is the leading financial application of Microsoft Bob. First, you are introduced to another assistant: Lexi.

Considering that Checkbook is a fairly large application, having a tour makes sense and matches the philosophy of Microsoft Bob: “Explain everything”.

The application is divided into multiple sections:

• The Account Book
• The Bill Basket
• The Report Folder

In the account book, you add your various bank accounts for payments and deposits. You’ll record all your transactions there, so you see exactly where your money goes.

Next is the bill basket. It contains your upcoming bills and deposits. Thanks to the integration in the Bob Calendar, you’ll never miss a payment again. A payment or deposit will be automatically recorded in the account book when it is due.

The third and final section is the report folder. As the name implies, you can create all sorts of reports here to check your financial health.

After showcasing the different areas, Lexi continues with the initial account setup.

Ironically, one of the first options shows that Microsoft didn’t have a clear target audience for Microsoft Bob: You can import an existing Microsoft Money file. If you already have a financial application that offers more options than Checkbook and is way more sophisticated, why do you even want this… downgrade?

The tutorial itself consists of several steps. You add your accounts, your first round of upcoming bills, and your paycheck. Additionally, you can import these transactions to your personal or household calendar, the latter being shared across all users with an account in your Microsoft Bob installation.

Bob Checkbook also provided an online service: Pay On-Line. Using this (now defunct) service, you could send payments to individuals and businesses in the US - right from your computer and in the blink of an eye.

Once you manage to get past the tutorial, Lexi will not be as intrusive as Rover in Letter Writer. On subsequent starts, you can get straight to the various areas of the program without having to look at how to get rid of too much helpful advice.

The Financial Guide

Bob Financial Guide is best described as a weird mix of a tutorial on life and creating oddly specific lists.

You start with an overview covering important aspects of life: Finance, buying a house, some personal milestones, your retirement.

Here, you can either modify the premade lists or generate your own.

Sure, some things in life require quite a lot of planning, but I don’t know if Microsoft Bob is the right tool. It works, but it feels clumsy, and I had a hard time finding the lists I created — did I put them in “Buying a Home” or “My Home”? I am trying to remember.

The Household Manager

Essentially, the Household Manager is the same as the Financial Guide, with different topics. And if I said “oddly specific” for the lists in the Financial Guide, then I have to say that we are entering the “absurdly specific” territory for the Household Manager.^

It suffers from the same flaw as the Financial Guide: It is easy to add information, but finding it again is hard. I appreciate the included cat manual, though.

E-Mail

Bob E-Mail was an E-Mail service provided by MCI Mail in collaboration with Microsoft. After signing up for their service, you get a nice @bob.com address to send and receive emails. Thanks to the integration into Letter Writer and the Address Book, you could send messages directly through these applications.

Unfortunately, the service is long gone, so there’s nothing I can show except for the startup screen.

The Address Book

The Address Book integrates with Letter Writer and Bob E-Mail. You can add, modify, and find addresses and use them as recipient addresses when writing a letter or sending it electronically.

It is simple and effective - exactly what you’d expect from an address book.

GeoSafari

GeoSafari is the only educational title and thus more geared towards children. This time, Hank will replace Rover, who will guide you through the program.

The main objective of this application is to solve geographical puzzles: find capitals and countries, name monuments, have fun with flags, and visit the solar system.

Feeling at home

Microsoft Bob provides an advanced customization system. You start in your living room, but there are more rooms to explore. Functionally, the rooms do exactly the same: They contain objects that either start programs or are purely decorative. Objects can be added, replaced, or rearranged.

The only room that works slightly differently is the personal room you selected when you launched the application for the first time. It will be marked as “hidden”, so the other users won’t be able to see it. In addition to the premade rooms, you can create your very own rooms. There’s a surprisingly extensive catalog of objects to choose from, providing a high level of customization.

However, transitioning between the different rooms takes quite a lot of time, even on the Pentium with 75 MHz backed by 16 MB of RAM I’m emulating for this review.

Conclusion and legacy

Microsoft Bob is one of the most spectacular product failures the company ever experienced. Reviews and sales were so bad that they discontinued it in early 1996, giving it a lifespan of just under a year.

Microsoft Bob had high system requirements and even felt slow on PCs faster than standard hardware at the time. Combined with a retail price of $99, which adjusted for inflation equals around $200 in 2024, the limited set of included applications wasn’t helping sales either. Initially, Microsoft planned a whole software ecosystem around Bob, but in the end, only Microsoft Great Greetings, a software for creating greeting cards at home, was released specifically for Microsoft Bob.

Looking at the visuals, the number of different objects, and the written content (remember, there’s a tutorial on how to handle your cat!), you can clearly see that the development team and designers put a lot of effort into Microsoft Bob.

Do I think it is a bad product? No, but I think it is pointless. It looks nice but provides little additional value. The bundled applications are stripped down, redundant, and sometimes even hard to use. Sure, you can add your Windows programs to Bob and assign them to objects, but this will make things way slower than just starting them through the Program Manager. All in all, it feels like Microsoft Office: Preschool Edition or a weird crossover between Windows and The Sims.

My recommendation for 1995 computer users: Get a good video tutorial for Windows 3.1 instead and learn how to use the real thing.

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