A datum describes the model that was used to match the location of features on the ground to coordinates and locations on the map. Maps all start with some form of survey. Early maps and surveys were carried out by teams of surveyors on the ground using transits and distance measuring "chains". Surveyors start with a handful of locations in "known" positions and use them to locate other features. These methods did not span continents well. Frequently they also did not cross political borders either. The "known points" and their positions are the information that the map datum is based. As space based surveying came into use, a standardized datum based on the center of the earth was developed.
Every map that shows a geographic coordinate system such as UTM or Latitude and Longitude with any precision will also list the datum used on the map.
The Global Positioning System uses an earth centered datum called the World Geodetic System 1984 or WGS 84. WGS 84 was adopted as a world standard from a datum called the North American Datum of 1983 or NAD 83. For all practical purposes there is no difference between WGS 84 and NAD 83.
Most USGS topographic maps are based on an earlier datum called the North American Datum of 1927 or NAD 27. (Some GPS units subdivide this datum into several datums spread over the continent. In the Continental United States use NAD27 CONUS.)
In the Continental United States the difference between WGS 84 and NAD 27 can be as much as 200 meters.
You should always set your GPS unit's datum to match the datum of the map you are using.
On a USGS topographic map the datum information is in the fine print at the bottom left of the map. The datum will always be NAD 27. There may be information on how many meters to shift a position to convert it to NAD 83. Think of this as the error that will be introduced if you leave your GPS unit set to WGS 84. A dashed cross in the SW and NE corners of the map gives a visual indication of the difference between the two datums.
If you have somehow set your GPS to use the Borneo Datum of 1818, it's hard to say how far off you position may be. Let's just sat that this "datum thing" is something you need to pay attention to.
If you are coordinating with aircraft, they will likely have their datum set to WGS 84, as most aviation charts now use WGS 84. Should you worry about the difference in datums? Typically a pilot will not have any difficulty locating you on the ground if you can get them within several hundred meters of your location. If you are engaged in a mission that requires more precision, then your datums should match.