Not sure how to proceed with my wild scheme

Is Jason an old fashioned type of guy? If so, he might be embarassed or upset that you proposed to him, instead of the other way around. I agree that dropping hints is the way to go in order to feel him out and see how he’d react to it. Here are some other hint dropping suggestions…

(this one I did to my BF)
I’m a sappy romantic and I would love to get married-I get those wedding magazines-my favorite is “The Knot” its like $11 but it only comes out quarterly I think and its big, thick, with lots of wedding party ideas. Well Ive been looking for a ring, just for fun. I found one that I just love-and I kept looking, and even after a year, it was my favorite. I cut the picture out of the magazine, included the page that listed where you can find jewlery by that designer, and sealed it in an envelope, wrote “Open when you are in a good mood” and slipped it in his nighstand. He didn’t say anything about it to me, but a few weeks later, I saw it wasn’t there anymore.

I asked my husband to marry me… and even if he is more traditional – try to keep the question popping low key (it was just me and him, lying in bed snuggling, nothing special – I just said “Hey, you wanna get married?” and that was it), it would reduce your nervousness and his awkwardness at being the ask-ee, rather then the ask-er. Also, it leaves things open if he doesn’t want to say yes at the time, rather then being pressured to in a fancy set-up.

Good luck with whatever you decide to do!

This is in response to dragonMedley: There are some practical sides to being married. I watch The View TV program and Joy Behar got married this past summer to the guy she has been with for 30+ years after stating numerous that it would NEVER happen. What changed her mind was a lesbian couple she knew that when one of them was hospitalized and died, that her partner was not allowed to visit her or have any input into her treatment including Do Not Resusitate and also not allowed any input into the funeral service. I lived with my husband for almost 10 years before we got married. 14 months after the wedding, he died. If we had not legally married, I would have not been able to prevent his ex-wife from taking over everything, or his parents which was about the same in awfulness. The will would not have made any difference, it doesn’t get read until much later, often insurance income is delayed or denied. Aside from the feelings about marriage, the legal ramifications need to be considered. Also, relationships are living things and if they don’t grow, they often die. This can happen both in and out of formal marriages, but are more likely to happen in less formal arrangements. I’m just saying….

If you have declared yourself as common-law on all applicable documents, then it is as if you were married (more or less), in Canada. Wasn’t aware that it wasn’t the same in the states. Kinda forces your hand, doesn’t it?

Well, you could do what my brother did with his girlfriend and ask while he’s on the toilet…. that was unexpected time to ask and they were alone! HAHAHA!

Whatever you do, good luck!

Haha, that is hilarious Drag0nfeathers, thanks for making me smile

Yes, I believe the exact words were “Honey, you stink, but I love you! Will you marry me?”