Asking awkward questions

So I am supposed to go on a info-seeking mission to the East Bay at some point to find out if a certain guy is engaged. I guess I could just ask him point-blank, but the problem is that I don't really know him too well. Oh, and he's one of these formal, reserved, east coast types. He is also one of these serious eldest child types. (Note: I am not mocking these types. I can caricature these two types, b/c technically, I'm one of these types as well, except that I occasionally need to be frivolous as well.) In other words, he is the very sort of person that I'd have a difficult time extracting this information out of.

This could happen one of two ways:

1) The "subtle" way-- probably the method that my friend prefers, but I can see myself spending hours at this pizza joint in Oakland, half paying attention to his conversation, and half trying to find an angle to subtly work this whole engagement thing into this conversation. Hmm. What would be likely to get him to open up about his personal life and fiancees or lack thereof to someone who has hung out with him maybe all but two or three times? Maybe I need to conjure up an imaginary fiance of mine. I'll tell him that I'm engaged, and then hopefully, he'll say, "me too", or not. Oh wait. Scratch that. I don't have a ring that could even remotely pass for an engagement ring. . .. NM. :-P

Thus, I think then, I'll go with method #2:
2) The "ask point-blank" way-- I'm usually not a "point blank" asking type of person, especially if I were interested in this particular guy. However, in certain situations, and with certain people, I can be very point blank to the point of probably being rude.

For example, I once saw $120 per spoon spoons from Tiffany listed on someone's registry. I mean, wth. Granted, I know it is a registry and you are supposed to request things you wouldn't buy for yourself, but I was looking for something appropriate to give to a "sort-of-but-not-close friend" level, and I think the cheapest option were these $120 Tiffany spoons. Ok, I'm majorly digressing, b/c this $120 spoon thing really baffles me, but do people a) suddenly take up an interest in $120 per utensil place settings just b/c they are getting married? Or b) do people have these wish list of things they want-but-will-hold-out-till-they-get-married? B/c although I might upgrade from my el cheapo Ikea silverware, I don't think I will ever suddenly want $120 spoons just b/c I am getting married. But on the second possibility, again, I understand to an extent about people holding back on buying things like the cuisinart big mixer thing. But what if you don't end up getting married? I mean, if there is a $120 spoon that you really want, why don't you just get it instead of waiting for the big day?

Anyway, So I called my friend, the groom who had probably nothing to do with this registry and asked-- "So you're like 45 or so. The average life expectancy is about 87, so we'll tack on a few years and make it 90, which means that you've finished living half of your life already. And right now, you are using what sort of spoons? Oh. Mismatched from good will? Yeah, me too. So tell me. What is the rationale behind you at your halfway point in life suddenly deciding that you have to get $120 spoons. I mean, if you were going to get maximum use out of them, then shouldn't you have bought them way earlier? Or do you suddenly at 45 have a newfound appreciation for high-end spoons?" We have the sort of relationship I can get away with asking such blunt questions, b/c that is how I think we first met.

But back to Mr. eldest child/east-coast reserved type. I'm not sure how point blank I can be with him. Mr.-$120 spoon can roll with the punches and take my line of questioning/uncouthness. I'm not sure about Mr. is-he-engaged. Will he be taken aback? Get flustered? Get mad?

Since I am not asking this information for myself, but rather on behalf of someone else, I feel less inhibited. All the same, I still probably need to find a nice segue into, "so, are you engaged?" As I was telling my friend, if it were left up to me, this is how the conversation would transpire:

(Setting: hip-ish restaurant in the east bay. We are almost done eating our main meal. Actually, we could have just finished ordering appetizers, but somehow, I think, just in case this doesn't go over too well, I will save it till we are both almost done with the meal. Mr. possibly-engaged is updating me about his summer plans.)

Mr. Possibly-engaged: ". . .so I really want to summit Mt. Kilimanjaro w/o the help of Sherpas. I've been doing some conditioning and training, etc. and have been keeping myself busy."

moi: "Wow. I just did my big travel thing a month ago, so probably this summer, I will stay put. Maybe date around a little. Look for a new job. Elope. Speaking of eloping, are you engaged?"

Mr. Possibly-engaged: "shemme?"

moi: "Oh, I'm not propositioning you or anything. I'm just idly curious." (Actually, I am not really idly curious at all, but I'm asking this on behalf of a friend. I actually really don't care if you are engaged or not, other than whether the outcome will make my friend happy. I want her to be happy, so in this sense, I guess I indirectly care. However, since I can't actually tell you this, I'm feigning idle curiosity.)

Does anyone have a less overt way of asking someone if they are engaged? I mean, with females, it's a bit more obvious, but w/ guys. . . they don't go around sporting engagement rings. (They really should though. Sometimes this is very critical information.)