Miss Information,

How do I bring up marriage without sounding like a crazy person?

By Cait Robinson

Have a question? Email . Letters may be edited for length, content, and clarity.

I've been with my partner for two years, and they've truly been fabulous. It's been long-distance for the last year, though I'm hoping to move back to his area in about another six-to-nine months. We're compatible in all of the big areas of a relationship: the way we handle money, our thoughts on having kids, our social/political/environmental views, our tastes, our adventurous personalities, our feelings on monogamy, our occasional desires for an intensely sexy homebody weekend in which all we do is eat and sex and sleep and sex. It's really good. I love him deeply and know I want to be with him for the rest of my life. By the way, I'm thirty and my partner is fifty. Yeah! Twenty-year gap ain't shit!

So I'd really like to know how to bring up the opposite of that conversation — the "I want this legal and social contract, the one that lets me be your caregiver when you are sick and you for me, the one that recognizes we are partners for life, the one that will announce to the country and the world that we trust one another with big decisions, allow the other to speak and act for us in our absence, and promise to continue going on sexy travel adventures and having sexy stay-at-home weekends — forever" conversation. It's a little loaded, you know? We've talked about long-term plans, in the sense of saving for trips five years out, getting ready for my move, adjusting life for pets, etc. But neither of us have brought up marriage yet.

How do I do that in a not-crazy-sounding way? How can I smoothly introduce the idea that I'm considering proposing to him in the next year or two? Why am I nervous about coming off as crazy-sounding? What's up with all the stereotypes of women being harpies and wanting rings? I don't want an engagement ring to feel secure in my relationship; I just want to have a normal conversation about being together in a permanent way.

Ahhhhhhh!

— I Need a Script for My State of the Union Address

Dear I Need a Script,

If it doesn't work out with him, want to be my roommate? You sound like the fun kind of neurotic. I wish I could give you a paint-by-numbers proposal, but if you were to put your letter into a sieve and shake real hard, I think you'd find you wrote one yourself.

First-off: I love that you view the issue as "I will propose to him in a few years," not "I need to cajole and con him into proposing to me, argh femininity is so hard!" So you get an automatic standing ovation for that one. That said, pro tip: if you don't want to have a crazy-escalating conversation, don't end it with "Ahhhhhhh!"

The best way to keep a conversation like this casual is to make it casual. Lounging, watching TV, and turning to ask, "What do you think about marriage?" will be a very different conversation than meeting him at the door in a power suit and saying, "Sit down. We need to talk." Starting in the abstract is always helpful, too. If you start discussing marriage as a concept, you will naturally funnel down to marriage in the specific. You can also broach the topic by discussing a friend who is getting married, or a conversation you just had with a friend, or this really adorable ring you just saw in a store and please please please because ladies be wantin' rings! (The latter option must be accompanied by a dog-whistle-pitched shriek.)

Though you may be mulling this over intensely, he won't necessarily read that on you. Just make sure you're not obsessing to the point of hopes he may not be able to fill (which I doubt you are). If you need validation that your desires are legitimate, here it is: it sounds like your expectations are spot-on, and you are allowed to want marriage without buying into some glassy-eyed, anti-feminist agenda. Just take a few deep breaths and I predict you'll do just fine.

Dear Miss Information,

My on-again off-again significant other of three years was recently approached by — and proceeded to do some heavy flirting with — a woman I have known for some time. (We live in a small town.) I've always considered her one of the most beautiful women I know, with long, black, curly hair, milky skin, and a big smile.

They've gone out a few times, and I'm involuntarily being kept in the loop by our group of friends and Facebook. He started calling less and less and finally dropped off all together after he asked to be "just friends" and I said, "No, thank you."

I have never felt so insecure in my life — except maybe for grade nine, when I could have been awarded "worst case of acne in school" — and I'm about to hit forty. I know objectively that I'm pretty, I have a great body, I'm sexually open and fun to be around. I have enough single male friends to prove it. But I'm about to run into these lovebirds everywhere, and it's going to impossible to forget how much of a better option she appeared to be. How do I keep myself sane?

— Green-Eyed Monster

Dear Green-Eyed Monster,

In a case like this, it's not that she's a "better" option, it's that she's a "newer" one. At the beginning, a relationship is entirely possibilities — there's no baggage, no "remember when you left me at the gas station on our road trip," no "how dare you call my mother that?" By cutting things off with you and starting something entirely new, he gets a fresh start. New relationships allow each of us to put our best foot forward, without having to deal with someone who has any dirt on us.

This is not to disparage the relationship you two had, but just to contextualize the breakup. It doesn't mean that she's in any way better than you, period. No matter how "over" someone you are, it still sucks when you realize they're with someone else.

If he's seeking new horizons, you get the chance to do the same. So start by reminding yourself that it's not "you vs. her." It's him moving on, and you having the freedom to do the same. And that's an opportunity dressed as a suckerpunch. Treat this as a case of "living well is the best revenge." You're only in her shadow if you put yourself there. 

If you run into them, hold your head high, be warm and gracious, then excuse yourself from the situation. Keep reminding yourself of your own strengths and the benefits you reap by being single. Take a walk around the block; take deep breaths and call a friend, if you need to. (We've all done it.) Act like it doesn't bother you, and eventually it won't.