What exactly are the differences between a "dating" relationship and an "engagement" ?
For me? Engagement means "We're now planning the wedding" plain and simple. If you aren't ready to sit down and plan a wedding, don't get engaged, I have no tolerance for this "Let's get engaged while we're in college and wait 5 years before we actually have a wedding" stuff
Dating and Engagement are, for most people, just two different commitment levels. Dating is "getting to know you" -- Engagement is "I know you and I want to marry you."
What sort of discussion and activities belong in an engagement that don't belong in dating?
I don't personally consider any topics "off limits" per-se since dating is the phase where you really need to get to know the other person; however, the pace at which you take certain topics may be important.
If you already have a female friend that you want, do you date, or can you just skip that and propose and then get engaged? (Assuming she says yes).
Regarding proposing to a friend... If you've gotten to know each other very well, have an attraction (mental, physical, spiritual, whatever is important) and a compatibility that you clearly recognize, then sure. Why not? I will admit I hadn't thought of doing it quite like that, but since you bring it up, I see how real reason not to! As you said, assuming she says yes
I tend to think our modern dating cycle is cumbersome, annoying, far too long and at times entirely immature though, so I'm somewhat biased in favor of shorting dating cycles and getting right to the point. ("Do you want to get married or not"
)
The key is just making sure you know this other person. For some people the level of "knowing" doesn't occur during a normal friendship, and in my opinion the engagement phase should NOT be an "extension" of the dating phase. Engagement is "plan the wedding" in my book and nothing more. But if you've gotten to know this friend to a level you believe is entirely reasonable that progressing into a marriage is something you think would work, then again I don't see why not.
In a case like this though, I'd probably make a "proposal" in a less conventional way, somewhat akin to what myself and my husband did: Talk about it. Talk about your compatibility, the way you see yourselves together in the future, and make sure you're on the same page. My husband and I didn't have some "surprise" proposal... we talked about marriage. A lot. And when we were ready, we decided it was time to get engaged because we were simply ready to plan the wedding. That was about 6 months in (the engagement) and another 6 months to plan the wedding. We've been together for 5 years in total, 4 of them married, very happy just for the record
These are just my personal thoughts.