How do I talk about getting engaged without making my boyfriend feel pressured to propose? (33M) & (28F)

[u/Hour-Shine-7205]

My boyfriend (33M) and I (28F) are coming up on our third anniversary next month. I love him and want to spend my life with him. He’s been open about seeing a future with me and wanting to propose, but we haven’t talked about when.

This year has been rough. We’ve dealt with job loss and a death in the family, so I understand that things may not have gone how he originally planned. We’re still strong and happy together. We live together, have traveled abroad, and met each other’s families early on. We talk about having kids and growing old together, so getting engaged feels like a natural next step to me.

I’m hoping he proposes around our anniversary, but he hasn’t said that he will. There haven’t been any obvious hints, like asking about my ring size or what I like. He offered to pay for a manicure and pedicure at one point, but that fell through after some car issues last month. I know a lack of hints doesn’t necessarily mean anything, but I’ve been wondering...

Our lease is also up in a few months, and I’m hesitant to sign another yearlong lease without knowing where we’re headed. I’m worried about staying in a relationship that isn’t going anywhere. I don’t want to spend years hoping for a commitment that never comes. Hearing that he wants to marry me is reassuring, but eventually, I need that to turn into action.

I’ve told him that I want kids by 32 and that I want to be married before having them. He’s also been very clear that he wants kids and a family. I feel like almost three years is a reasonable amount of time to know whether you want to marry someone.

He was engaged once before, about a decade ago, and they got engaged after a year. I try not to compare, but sometimes that does get in my head.

There’s also the ring. I’m worried he may still have his ex’s engagement ring and might use it to propose to me. I don’t know if he’s actually planning that, but it would really hurt to be given a ring he picked out for someone else. It’s not about wanting something expensive. I’d just want it to be something he chose for me. How do I bring that up naturally without assuming he’s about to propose?

As for the timeline, would it be reasonable to leave if we’re still not engaged a few months after our anniversary? I love him, but I don’t want to keep putting my own plans on hold indefinitely.

But the last thing I want is to tell him all this and have him propose right afterward because he feels obligated or is afraid I’ll leave. I want him to want to marry me on his own. At the same time, I know he can’t read my mind, and avoiding the conversation isn’t helping either.

How would you handle this? I’d appreciate different perspectives, especially from men who have been in a similar situation.

[u/husheveryone]

INFO: Are you ::genuinely:: worried about receiving his ex’s former ring from a decade ago that you’ve never laid eyes upon?? 😳 Seriously, is that in this man’s character to do, or are you maybe catastrophizing? Common sense suggests he probably sold it ages ago if he’s ever been strapped for cash in the last decade like a lot of folks his age, but I digress.

Thing is, your 33M hasn’t even asked for your ring size, nor has he made any type of engagement-ish plans beyond some IDLE TALK WITH ZERO ACTION, at all, after 3 years and living together. So at this point you’re not even realistically on track to even get his ex’s vaunted recycled ring that’s, again, likely long gone by now. And you’re too timid to speak up about your concerns?? Come on. Stop being a Placeholder who won’t at least speak up now about your lease renewal. He’d be happy to keep you as a forever girlfriend for as long as you’ll continue to allow it.

Make your intentions known, and find out now so you can stop wasting time in a lease where your future husband cannot find you.

Relatedly, a 32F in your shoes with a looming joint lease renewal deadline asked a very similar question here on this sub just the other day. That OP was worried about hypothetically getting a shut up ring, and acknowledged she had violated her own personal standard by moving in with a boyfriend who hasn’t asked to be her fiancé yet. She got some good answers that also apply to your situation. She seems like she’s prepared to leave though, whereas you seem like you’re willing to waste a few more years on hope if he says the right stuff…