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Instant Messenging (Text Chatting)
Overview
OS X comes with iChat AV, while Windows XP comes with Windows Messenger. Both clients support buddy lists, the ability to chat with multiple buddies simultaneously, and "typing indicators" that show you when a buddy is typing a message to you. Both clients allow you to share files through your chat window, and both clients support "emoticons" (although XP's array is wider).
iChat is an AOL Instant Messenger (AIM) client, so it interoperates with AIM for Windows (and Mac). It also supports Jabber, allowing you to chat with anyone using any of these IM clients. .Mac users can also use their .Mac email addresses as their iChat buddy name.
Windows Messenger is a .NET client.
Mac OS X
Integration with OS X's Address Book means that your buddies are centrally managed and accessible via any other program that interacts with Address Book. This eliminates the need to maintain redundant contact lists. In addition - and perhaps more importantly - this lets you display your buddies' real names in your buddy list, as opposed to their screennames.

iChat's buddy list window, displaying contacts' real names
iChat has many display and sorting options for its buddy list window. In the buddy list, you can turn on or off:
- Audio/video status icons
- Buddy icons
- Groups
- Offline buddy display
You can also sort your buddy list according to availability, or by first/last name. Sorting by availability is convenient, as all buddies who are available for chatting (indicated with a green dot) will float to the top of the buddy list window (seen above). Idle buddies are indicated with a yellow dot, and away buddies with a red one.
iChat can also display some limited information about your buddies inline in the buddy list window. For instance, a buddy's idle time will display in grey underneath their name. Away messages also display in the same fashion, although they truncate themselves to one line due to limited space (hover over their name, however, and their full away message will pop up in a tooltip). If a contact is connected through a mobile device, it will say "Mobile" underneath their name.
In addition to being able to set a custom away message, iChat allows for an "available" message as well. This lets you display a status message without being away, to indicate that you are still available for chatting. In addition, iTunes integration lets you display the artist and name of the currently playing song as a status message. Unfortunately, these latter two features are only visible to other iChat users.
iChat relies on the buddy list as a visual notification about buddies changing their online status. If your buddy list is hidden, iChat's menu extra will display a list of your currently online buddies. iChat can optionally verbally notify you of any event: when a buddy comes on- or offline, when they send you text or audio chat invitations, etc.
Chat windows have numerous display options as well. By default, iChat uses speech bubbles to indicate who is talking (iChat calls them "balloons"):

You can display real names in addition to buddy icons, or, if you prefer, you can disable all of these options for a more traditional interface (buddy names at left, no speech bubbles). You can also set a background image for the chat window.
To set your buddy icon, you can drag-and-drop an image file directly onto the buddy list window. If you have an iSight, you can use it to take a picture of yourself. A listing of previously used icons will pop up when you click your own buddy icon in the buddy list window. Switching users/screennames can be accomplished by going to iChat > Switch To and choosing a different account. iChat can also automatically log IM conversations - their contents will be searchable through Spotlight.
Other notable interface features include:
- Cartoon-like thought bubbles indicate a buddy is typing a message to you (below)
- If your buddy list is sorted by online status, buddies will "slide" to the appropriate area in the list as their status changes
- Menu bar integration lets you see who's online without having to switch to iChat first
- When you initially receive an IM, the window is translucent; click it, and it will expand into a full window
- Expanding and collapsing of groups (if enabled) is animated
- Minimized chat windows smartly show the buddy icon of the person you're talking to, rather than a miniature version of the window
- Interface sounds (receive an IM, send an IM, etc.) are elegant and unobtrusive
- When iChat is in the background, its dock icon sprouts a badge to indicate how many messages you've received

Windows XP
XP comes with Windows Messenger, which is primarily designed for use in a business environment.

Windows Messenger's buddy list and chat windows
While Windows Messenger has an abundant array of emoticons to make chatting more fun, its business-oriented approach does not otherwise carry over well to a consumer setting. It has basic features, including grouping of contacts (both in personalized groups and online status), viewing by email address, and file transfer, but there are few outstanding features in the average home environment. For instance, Windows Messenger can't create or modify status messages (you must select from a built-in range), set a custom buddy icon, or work with multiple identities.
Because of Windows Messenger's business-oriented design, Microsoft offers MSN Messenger as a free download (though unfortunately it is ad-supported).

MSN Messenger's buddy list window
MSN Messenger is geared much more towards home users. It offers similar features to Windows Messenger, but adds:
- A more consumer-friendly interface
- Custom emoticons
- IM logging
- Custom status messages
- Buddy icons (referred to as "display pictures")
- Ability to display contacts as email addresses only
- Save and import contact lists
- Play games with your contact
- Send messages to mobile devices
MSN Messenger integrates tightly with other Microsoft services and products, such as:
- Hotmail
- MSN Spaces (you can quickly post new blog entries and view your buddies' blogs)
- The MSN Music Store
- MSN Search (a search button in every chat window displays the top results for your query in the window itself, or in a new browser window)
The most obvious consumer-oriented additions in MSN Messenger are the activities and games. Exactly which ones you can use depend on where in the world you're using it from, but common activities include MSN Calendar Sharing, File Sharing (an enhanced version of the built-in file transfer), and MSN Photo Swap (essentially a controllable slideshow). The games are all two-player (and most record your high score to compare with your buddies), although some include a one-player version for when your opponent has to return to the real world. All of these appear next to the conversation, and can only be used in a two-person conversation.

Playing a game with a buddy. The game attaches itself to the IM window, and resizes to fit the allotted space
Unfortunately, many of the better features in MSN Messenger come at a price. You can send "Winks" (short animations that cover the whole window) to other buddies, and use display pictures which react to the emoticons you use in a conversation, among other things.

"Winks" superimpose themselves over your chat window, and resize to fit the available space
But whilst you're free to make your own emoticons and buddy icons, only a handful of Winks - and no interactive display pictures at all - are included in the default download. Microsoft has ensured that the only free ones are advertisements (such as a Halo- or Adidas-themed range). Similarly, while you can send SMS messages to a mobile phone, you may be required to pay for the privilege (depending on your country or region).
Windows and MSN Messenger both allow the creation of impromptu chat rooms, simply by inviting more people into your conversation. Assuming they accept, any text messages you send, as well as winks, nudges and handwritten messages (see the Advanced Conferencing section) go to everyone present. Since anyone can invite additional people, you can easily end up talking to people who are not on your contact list. There are no "actual" chat rooms available from either Windows or MSN Messenger, and this implementation has two large issues:
- Any conversation with more than 20 people tends to experience a large amount of lag on slower connections
- The only way into the "room" is to be invited; if you exit, you can only re-enter if someone still in the room invites you back in
If your buddy list window is hidden, both Windows and MSN Messenger will spring up a notification in the corner of the screen nearest their system tray icon (next to the clock) whenever a buddy comes online (this notification style is sometimes referred to as "toast"). The buddy list, of course, is updated when it is visible. Windows Messenger can only notify you when a buddy comes online, as well as if they start a conversation or other activity with you; it uses customisable sounds for each event. MSN Messenger has a larger range of activities for which notifications will appear.

"Toast" pops up when a contact signs in
The advantage to Windows Messenger's method is that notifications will spring open in front of other applications so that you can always see when someone comes online. They disappear after a few seconds, but if such alerts are a distraction, you have some control over when they appear:
- Tools > Personal Tab > Check "Show me as 'Busy' and block my alerts when I'm running a full screen program such as a slide presentation"
- Tools > General Tab > Check "Display alert when contacts come online"
- Setting your status to "Busy" or "On The Phone" will hide any alerts that would otherwise appear
The following table summarizes and compares the features of iChat AV, Windows Messenger, and MSN Messenger:
| iChat AV 3.0 | Windows Messenger 5.1 | MSN Messenger 7.5 | Comments | |
| Supported networks | AIM, Jabber, Bonjour | .NET, SIP, Microsoft Exchange Server | .NET | |
| Ad-free | Yes | Yes | No | |
| Personal display/status | ||||
| Personal display pictures/icons | Yes | No | Yes | |
| Personal status messages | Yes | No | Yes | |
| Buddy Lists | ||||
| List buddies by real name | Yes | No | No | |
| List buddies as email addresses | No | Yes | Yes | |
| Group buddy lists | Yes | Yes | Yes | |
| View buddy's profile | Yes | Yes | Yes | |
| Address book integration | Yes | No | Yes | |
| Contact cards | No | No | Yes | Similar to buddy profiles, contact cards feature integration with MSN Spaces so you can see your buddy's latest photos and blog entries |
| Create buddy profile | Yes | Yes | Yes | |
| Chatting | ||||
| Typing indicators | Yes | Yes | Yes | |
| Cross-platform text chats | Yes | No | Yes | |
| Emoticons | 16 | 34 | 75 | |
| Custom emoticons | No | No | Yes | |
| Flash animations ("winks") | No | No | Yes | |
| Multiple simultaneous text chats | Yes | Yes | Yes | |
| Secure text chat | Yes* | Yes | No | *Via Jabber |
| Share files within chat window | Yes | Yes* | Yes | *Only one file can be transferred at a time |
| Display shared images inline | Yes | No | Yes | |
| Pen support | No | No | Yes | Write messages with a tablet and pen, or use your mouse |
| Extras | ||||
| Blog integration | No | No | Yes | Integrated with MSN Spaces |
| Chat logs | Yes | No | Yes | |
| Check email | No | Yes | Yes | Hotmail or MSN accounts only |
| Notifications | Yes | Yes | Yes | |
| Custom background images | Yes | No | Yes* | *Supports animated background images (in addition to static) |
| Background image sharing | No | No | Yes | |
| Play games with buddies | No | No | Yes | |
| Save/import contact list files | No | Yes | Yes | |
| Send SMS messages | Yes | No | Yes* | *Not free in all locations |
| Show current music playing | Yes | No | Yes | Buddies can preview the track through the iTunes Music Store and the MSN Music Store, respectively |
| Support for multiple users | Yes | No | No | |
| Attention notifications ("nudges") | No | No | Yes | |
| Parental controls | Yes | No | No | |
Conclusion
Out-of-the-box, OS X's offering (iChat) bests XP's (Windows Messenger) with more consumer-oriented features. Fortunately, Microsoft offers MSN Messenger for free download, which sports a feature set on par with iChat's.Mac OS X: 8
Windows XP: 5 (8)
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