Should I wait for him to propose?

I don't want to be pushy, but I want to have the conversation

Published December 9, 2009 11:10PM (EST)

Dear Reader,

Appointments, appointments, appointments. You'd think I was the president. Except they don't make the president pull his pants down so much. Do they?

Also getting my money stuff together for when I'm lying around in the hospital for days on end doped up silly. Lucky I have really good help with the money thing (see below). -- ct

Dear Cary,

I have been with my boyfriend for two years. For six months of that, we've been living together. We're grown-ups with enough of life behind us to know what we want from the rest of it. We're in love, compatible, and extremely happy together. Not to say we never have moments of frustration, and the stray medical issue or crappy job situation sometimes dampens the fireworks, but our life together epitomizes everything we've ever wanted in a relationship. I've been thinking I'd like to be with this man for the rest of my life, in that formal, official, traditional way that usually involves a few dozen relatives and friends, cake and quite possibly some dancing.

There's a complicating factor: I'm a relatively recent divorcée from a marriage that was emotionally manipulative, exploitative and draining. About a month ago, my boyfriend started asking questions about my views on and attitudes about marriage, but it didn't lead to anything. I'm concerned that it's because I didn't get my message across that "YES I AM TOTALLY OK WITH MARRIAGE. I'D SAY YES ENTHUSIASTICALLY!!" On me, suppressed anything looks and sounds like a bad case of constipation. Even suppressed joyful hope (or hopeful joy?). So maybe he thinks that I'm not ready.

(Note that I've never been awkward or uncomfortable with him about any other topic. It's just that this is so big!)

For a number of reasons, I don't want to propose to him. He's younger and less experienced in relationships, so I want to give him the chance to set the pace. I also want to be asked, rather than ask, because I enjoy his knack for romantic gestures. I don't want to ask him his intentions directly because I don't want him to feel the pressure of me Waiting For Him To Propose while he makes that kind of decision. As for the indirect route, he'd see right through a dropped hint.

Should I just wait it out? Bite the bullet and ask? Do something terribly clever I haven't thought of? Am I misinterpreting the situation? Let me know what you think the best course of action would be for me in this situation. Thanks!

Please Insert Clever Acronym Here

Dear PICAH (is that clever?),

You know what I suggest? I suggest that you continue to talk about marriage in an open-ended, non-threatening way, with the understanding that nobody's proposing anything and nobody's declining anything. You're just sharing thoughts and feelings. Maybe the conversation would go something like this:

Remember a month or so ago when we sort of talked about marriage?
Well, could we talk about it some more?
Well, I just wanted to talk about it some more.
OK, he says.
Well, you say, I want us both to be happy. Don't you?
Sure, he says. I want us both to be happy.
So it would be great if we both wanted the same thing.
Oh, yeah. That would be great.
But it would be sad if we wanted different things, you say.
Yes, he agrees, that would be sad.
So I'm scared, you say.
What are you scared of?
I'm scared that we might not want the same thing.
Aw, baby, he says.

Or maybe he doesn't say "Aw, baby." Maybe that's not his style. But he acknowledges that you have expressed a feeling and doesn't freak out about it.

Basically, you don't have to decide on a big thing like marriage right away. Instead, you have the courage to admit your fears and explore your wishes. You just explore and share.

So then he might say,

Well, what do you want?
What do I really want?
Yes. What do you really want?
What if I say what I want and it's not what you want?
That's OK, he says. We couldn't want all of the same things.

Maybe he's trying to get you to say what you want first. Maybe you want more couscous. Does he want more couscous? What about sleeping? Do you both like to sleep the same amount of time? What kind of pillow do you like? Have you been mildly unhappy with your pillow? What about his pillow? Sometimes when you just in together you don't talk about which pillow you like. Sometimes you end up with his pillow or he ends up with yours. Maybe he wants a new pillow. That would be good to find out. Asking, Do you want to get ... a new pillow? is easier than asking, Do you want to get ... married?

Keep it open-ended, talk about concrete things in the here and now. Take your time. As you explore these questions, ask yourself, what would marriage do for us? What would it require of us? How would it change things? What expectations would we bring to it? What were the marriages of our parents like?

Maybe some of that will work its way into the pillow talk.

Also, if you're talking about marriage, you're talking about money. So you could also talk about money. No pressure. Just sharing feelings. How do you feel about money? Do you hate money? Are you afraid of money? Do you hoard? Do you binge?

As far as that goes, I found a good person to help me with this money thing -- my friend and mentor Elizabeth Husserl, inventor of Inner Economics. She has a private practice in Berkeley where she works with people one-on-one, either face-to-face or via phone consultation, about their relationship with money. She also offers workshops. periodically (the latest one was last week!). I have learned a lot from her. I'll let you know when her next workshop is.

So ... Let's talk about money too, you say.
What about money? he says.
Well, money scares the shit out of me!
Me too, he says. Let's talk about rugs instead. Things will become clear.
Maybe, you say.
I think so, he says.
Bit by bit, you say.
Bit by bit, he says. Plus, I could understand if you were a little gun-shy.
Well, it would have to be the right person, you say.
Even so, he says. After what you've been through.
But with the right person ...
Even with the right person, he says.
You're sweet, you say.
I try, he says.

Hey kids! Follow me on Twitter!

What? You want more advice?

By Cary Tennis

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