My putting my foot down made him realize how much he doesn't want to lose me. No we are not engaged still lots more to figure out, but at least we are starting down that path.
Be wary. After five years, if you have this talk with him and you’re not engaged within the next three or so months he’s just stringing you along. If he wanted to be married to you he would be, that’s the sad truth. And be wary too of what your goal is here, it’s not to be engaged, it’s to be married. Engagement itself is meaningless other than to the two parties involved and their feelings, in reality it’s no more being married than your first date with someone. I know many women stuck in a never ending engagement, they get the ring and have a momentarily thrill and then it dies down and nothing happens (usually their boyfriends saying they can’t afford the wedding they [he] absolutely must have, while also not doing anything to save for it and rejecting her plans for a more affordable day with ‘but it’s the most important day of our lives I just want it to be special!’) which makes it sadly evident their partners didn’t want to marry them at all. A close friend of mine got engaged two years ago, we all met for coffee to congratulate them, gave a ‘you’re getting married!’ card etc. and when she was in the toilet I said to him how excited I was for them and asked if he had thought about timescales and he said ‘no, it’s more something for the future really, for Jess’. Same guy couldn’t afford a ring so instead of saving for some of the six years they’d been together for a cheap but nice ring he blew £1k on their shared overdraft buying it then gave it to her one morning, no ‘will you marry me?’ or effort or anything. She has a nice ring but she’s no more close to being married than someone who’s single tbh.
Threads like these are always full of ‘ask him, it’s 2019!’ and ‘why do you want a ring and a piece of paper?’ as if it’s trendy or cool to be to blasé about the commitment of marriage and uncool to actually admit it’s important to you.
In terms of wanting him to propose, I think that’s very sensible after so many years together, you’ve made your desire to marry clear so if he wanted to marry you he would have done by now. In a relationship where the two of you disagree on something so fundamental it’s on the reluctant partner to take the step of showing the other that they’re ready and want this, not on the ready partner to try and stronghold the reluctant one into it. If I wanted children and my OH didn’t I wouldn’t be trying to cajole or beg or persuade him into it because having kids, like getting married, is something you need to enter into willingly or enthusiastically. Women proposing is fine but not when their partners have made it clear via words or inaction they’re not interested in marrying them. You’ll end up with a reluctant husband you have to drag to the alter at best. In your shoes having been strung along for years by a man telling me he wanted to marry me while not actually doing it damn right I’d want him to put a bit of effort into proposing to believe he’d actually changed his mind and wanted to marry me. And a proposal with a date, not a ‘shut you up’ ring! I think that’s only natural, otherwise you’d be proposing to someone you know doesn’t want to marry you. Where’s the dignity in that?
Marriage is just a piece of paper to some (in the same way a job contract, a will, a speeding fine are all just ‘pieces of paper’ which represent a legal formal contract and agreement recognised in law with the attendant expectations, responsibilities and rights) but if it matters to OP she deserves to feel okay about that. If marriage was unimportant gay couples wouldn’t have fought so hard for the right to marry. There are differences between cohabiting as boyfriend and girlfriend and marrying, practically, and there are emotional meanings to many people too.
I took the risk of getting pregnant unmarried to my OH as we’d both discussed marriage and agreed we wanted to be married before we had a baby but didn’t want to delay TTC due to health issues, we got lucky enough to fall pregnant immediately and I didn’t sorry about marriage as I knew/believed/hoped he’d step up based on what we’d previously discussed. Though I was admittedly willing to take the risk he wouldn’t, as i would rather have had a child and not married or married later than not had a child. At several months pregnant he proposed (the big romantic proposal that people don’t seem to think exists haha, not that I expected or would have needed that!) and within a week we’d set a date, before baby arrives. Short engagement, simple ceremony and celebration.
Your OH has led you down the garden path and you need to decide whether you’re willing to stay with him how things are, and if not I’d be setting a date in my own mind, if we’re not married a year from now I’m done. Don’t share it with him. You want to get married because he wants to marry you not as the least worse option open to him. As the year moves on and you’re only a few months from the deadline and not engaged it’ll be obvious it’s too late and you can decide whether to walk and find someone who will willingly and enthusiastically marry you under his own steam without needing to be cajoled into it.
Keep us posted!