Just keep it calm and steady and do it when you both have all the time in the world to chat about it. Like at home relaxing on the couch.
Something like, ” Hey we have talked here and there about marriage and kids but havnen’t gotten specific. Id really like to be engaged by our third anniversary. How do you feel about that? “
Think of this chat as the first of a series of chats.
The first chat gives you an idea of where his head is at in general, after 2 years he should at least be open to talking about it, and if you are lucky excited and on board 100% But don’t worry if he isn’t commiting to a timeline right away. Just gently probe for information in the chat.
The next chat you can do 2 months later, “Hey remember we talked a few months ago about getting engaged. I would really like to be engaged by (this time say month of your 3rd anniversary) Are we on the same page with that? At this point he should have thought about it more since your first conversation and have stepped toward the idea way more. Again maybe he is 100% on board. If he is hesitating you can ask him what makes him hesitate? Ask when he would be ready.
The third chat do 1 month later. “Hey, just checking in about the last conversation we had about getting engaged. Are we on the same page with being engaged by ( month of 3rd anniversary)? If he still hesitates a lot, or makes up excuses that don’t seem right you are going to have to be more direct. For example, he makes an excuse, you ask him what he is doing to overcome that excuse. Because an excuse with no plan to correct it is just that a bullcrap excuse. You should expect if he has a reason why not, that you deserve an answer on what he is planning to do about that. If you still get all kinds of push back or vague answers you gotta end with something like this. ” Ok, I hear what you are saying. For me I am not willing to give an unlimited amount of time to a relationship that isn’t moving forward. That wouldn’t be right for either of us to waste our time. If we get to ( you pick a month where if he hasn’t proposed you will walk out) August and there is no proposal we are going to have to talk about what we are doing and if this relationship is serving both our needs.”
THen you drop it until the walk date. He doesn’t propose you walk. You made yourself perfectly clear on what you needed. You openly discussed it and tried to address all concerns.
Here is the key to this process. Between conversations about engagement you DO NOT drop hints, nag about it, make little side comments etc. If he brings it up great, if not you save it for the serious conversations.
* If during any of these conversations he gets angry, defensive, doesn’t want to discuss it at all, leaves the room etc. than you have your HUGE RED FLAG. If he loves you he will be open to discussing it calmly and respectfully. If he can’t do that he is telling you he resents you asking. People don’t resent other people for discussing something they want to do, even if it is someday. He should be open to it, and at best excited.
Keep us updated!!