One of the great debates about CCW is behavior modification. As with most debates, there are two extreme positions, which I define in the CCW case by the following complexes:
"Superman"- I have a CCW permit, a tricked-out custom 1911 IWB with two BUGs, and I am going to go wherever, whenever, and however I please. This is the type of person who is setting themselves up for disaster, like intentionally walking through the bad part of town (while having no business being there), simply because you can. In the most extreme case, this person may border on vigilantism by trying to provoke an encounter by "innocently" flashing money or valuables.
"Hermit"- I have a CCW permit, but NEVER leave my house or property unless absolutely necessary, because I don't wan't to expose myself (or family) to ANY increased risk. This is the type of person who gets their groceries delivered, normally spends Saturday night loading ammo in the basement, and would never contemplate getting a baby sitter and enjoying dinner and a beer (or movie) in the "trendy" part of town. Hunting would be off of this person list as well, because other people in the woods have guns too, and you never know what they might do...
Most people on this board (I hope) try to strike a proper balance between the two as their life permits. The "Superman" mentality can get you into REAL trouble REAL fast. While there is nothing legally or morally wrong with the "Hermit" mentality, people who live like that probably are a little stressed out and don't have much fun in their lives.
I believe that I have found the proper balance for my MY life and MY family. Sometimes, my wife and I will be in the "questionable" part of town (e.g. East Colfax) late at night for a concert. Is this more risky than watching an on-demand movie from ComCast while sitting on the couch? Yes, of course it is, but sometimes we need to get out of the house for a while and take in some real culture. When we do this, we try to minimize our vulnerable time by parking close, staying in groups, maintaining good situational awareness, and carrying cell phone, flashlight, CCW as required.
Your mileage may vary...
In the case of my coworker and his gf, I think their evening plans were completely reasonable, and did not represent any sort of reckless behavior.