Here's a letter from Boco, via rpg.net:
I am writing a short story in which the characters go on a series of
increasingly ill-advised, illegal, and potentially dangerous dates,
starting with breaking into a Build-a-Bear Workshop after hours and
culminating in a bank robbery that goes south. I want about three other
dates in between those to casually mention and not really dwell on in
detail. What are your suggestions?
There's not a whole lot of room between breaking and entering and bank
robbery, so if you want a steady escalation, you might want to start a
little lower on the crime scale, but if you don't mind an uneven
progression, I do have some ideas.
The danger and ill-advisedness of these dates need not be directly tied
to their illegality. You could have the danger be due to the terrain, as
with a case of romantic vandalism where your characters might have to
climb a public monument to spraypaint their message of love near the
top. Alternately, the danger could come from other criminals. Gambling
in an underground casino, or even playing on a playground after hours
(when the park is taken over by drug dealers, prostitutes, and their
customers) both present certain risks.
Finally, if your characters are psychopathic enough to go for it, even
the most mundane and domestic activities can be ill-advised and
dangerous if done as part of a home invasion. Snuggling on the couch,
making fajitas from leftover chicken, or dancing to a romantic song on
the radio are downright creepy if you have a family of hostages tied up
in the other room (and, if you're going for something a little more
innocent, they are still pretty damned criminal if the homeowners are
away on vacation).
I hope that helped, and good luck with your story.