Not Engaged Yet

How to have "The Hint" chat (or whether to do it at all)

How, if at all, do you have the discussion with your longterm partner about how you'd like to get engaged and proposed to in a more traditional way, with it still being surprising? I'm worried about giving him anxiety or pressure, but I don't want to not give him any idea what my timeline or hopes are either. I see those ads occasionally on social media with prompts to "drop a hint!" and send a literal link to ring designs. Do women actually do this?! I asked my mother for advice, and it wasn't of much help, as she is of the generation when any discussion of marriage was, in her words, "your father and I 'discussed' marriage when he got down on one knee and asked me to marry him and I said 'yes!'"

Background: My boyfriend are in our mid-30s, and have been serious for about a year and a half. Our anniversary of our first date is in the fall. We've had explicit clear chats in the past about wanting the same things with each other (marriage, kids, area to live, even what our last names will be when married), and he's previously stated he'd want to be married "by 2025." But I've no idea how to initiate any discussion of when we ought to get engaged, how I'd want that to happen, rings, method of proposal, etc. I've friends who went ring shopping months with their partners months ahead of any proposal, and even others who've discussed specific place & date of proposal. I've always wanted it to be a surprise, but my boyfriend is not the kind of guy who jumps head first into something like jewelry selection. He is gainfully employed with a very well-paying job, no debts, and we are planning to move in together and find our own placed by the end of the year. Neither of us have any plans to move, go to grad school, or any other so-called milestones in life we're waiting on completing/starting

TL;DR version In my head I just want to scream "please propose to me by [date/event]!" to him. The way everything seems to be done these days is super unique for everyone, and I'm at a loss for what's advisable and what's not for when you want to make your intentions known, but still believe in some romance and spontaneity. 

Re: How to have "The Hint" chat (or whether to do it at all)

  • The older I get (I'm 43) the more I think that a relationship is a partnership and any proposal needs to be a formal means to an agreed upon end. 

    If you want to marry him then tell him.  Be clear with what you want because this is someone you intend to live with and build a future together that has major financial implications.  This is the first conversation that you need to have and if you can't have it then you're not ready to be engaged.
  • I'm probably about your mom's age (I have a 36 year old daughter). My H and I talked about marriage and even looked at rings. I didn't know if he bought one or not until he proposed a year and a half later. I didn't give him a timeline but we did have some major milestones to reach first and I was aware of that.
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