"enjoy your weekend!" -> "what weekend?"

According to dictionary.reference.com, the word "miss" has 14 definitions. Among which when it is used as a verb with an object, it could mean one of two things:

• to fail to encounter, meet, catch, etc.
• to regret the absence or loss of.
  

The two are slightly different - regret hints of emotional attachment...

When I "miss" someone, does it mean that i'm just commenting that i failed to "encounter, meet, catch, etc" that person, or is it that i "regret the absence" of that person?

Gonna be working the weekend. sigh.