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How to casually bring up marriage

Valentine’s Day is coming, and if you’re in a committed relationship, you might be asking yourself: Will he pop the question? You know the question I’m talking about: the Big M Word. Marriage.

Four years ago, I asked myself the same question, and … he did. Pop the question. On Valentine’s Day. Which, of course, all my girlfriends guessed beforehand. It all sounds so easy and romantic, right? Like something out of a Meg Ryan movie?

More: Woman’s reaction to proposal is totally over the top (VIDEO)

Wrong. Talking about marriage is not easy, and you never know how hard the conversation is going to be until you have it. Granted, my man was cool and collected. He knew he wanted to marry me, so talking about it didn’t send him running like a frightened squirrel.

What about your guy? Is your guy cool as a cucumber or more like Tigger, leaping from tree to tree whenever he hears you say “Maybe” for fear that “Maybe” will turn into the word “Marriage?” If so, we’ve got some tips for starting the slow walk down that long aisle. Don’t worry; I’m an expert. Sort of.

1. It helps if a friend just got engaged.

It’s just after Christmas, right? I’ll bet someone you know got engaged. Bam! Perfect opportunity to bring up marriage in a safe, casual sort of way. Open a bottle of wine, curl up together under a blanket and just say it. Something to the effect of: “It’s so cool that so-and-so got engaged. Don’t you think they’re perfect for each other? About time he popped the question.” Your guy’s reaction is telling. If he agrees, then you can let it go, relax and remind him how lucky he is by having mind-blowing sex later. If he gets jittery or disagrees, red flag. Tread lightly, because this conversation could turn into an argument pronto.

More: Romantic holiday proposals to make you believe in true love again

2. Talk about your parents’ relationships.

Part of serious dating is knowing your boyfriend’s family, which means you’ll know if his parents are still married, divorced or even remarried. A conversation about his parents’ relationship (and yours) can be useful for plenty of reasons. One: You just generally get to know each other better. Two: You get an idea of what he thinks about marriage as an institution. If his parents are still together, winner, because he’s had a healthy relationship model to look up to all his life. If his parents are divorced, see if he seems sad about it; that might mean he regrets his parents’ unhappiness and hopes to one day prove that marriage can work. If his parents are divorced and he’s angry, marriage might not be in his long-term plans. He may be embittered by his past, which doesn’t bode well for your future.

3. Have your dad ask, “What are your intentions with my daughter?”

I’m kidding. Please, don’t do this. Ever.

4. Watch a movie with infidelity and then discuss.

Best movie for this: Unfaithful. It’s got lots of great sex. Seriously, though, see how your guy reacts to films where marriage is torn apart. What kind of emotions does this stir? Quiz him even. Ask the big one: “Honey, do you believe there’s one person for everyone?” Getting him thinking about monogamy on the forever scale is basically a coded way to discuss marriage. Plus, as I said, movies with infidelity usually involve lots of sex scenes, and what guy doesn’t like watching sex scenes?

More: Swoon-worthy Valentine’s Day engagement stories

5. Go on a wedding date.

If he invites you to a wedding, bingo, you’re in. You’re marriage material. You don’t have to be afraid to ask him to a wedding either; just say “open bar.” A wedding gets the gears turning. Seeing friends happy and in love will make your man want to cuddle closer to you and slow dance to Sinatra. If he doesn’t, I’d be worried.

6. Play with Pinterest.

Most men I know aren’t on Pinterest, but that doesn’t mean you can’t use it to your innocent (albeit sneaky) advantage. When sitting on the couch with him, just casually browse through some jewelry boards. Point out pretty emerald or ruby rings you like so he knows your style. (Stay away from diamond rings; don’t want to send a nervous dude into convulsions.) It’s important to plant the seed, but you also don’t want to end up with a ring you hate. Let him know subconsciously what’s on your mind and what you like, and sooner or later, he’ll get the hint.

7. Watch funny proposal videos.

Totally innocent. There are tons of funny proposal videos on YouTube. Find a particularly funny one and say, “Honey, you have to see this!” Funny is good, because if you try to get too romantic on him, he might see through your ploy and do the slow back-away. But just watching a proposal video that’ll make him laugh will get him thinking … and thinking … until maybe, just maybe, he’ll think he could do a better proposal and wouldn’t that be fun! Voilà!

More on marriage

An evolution of marriage on television
Best romantic movies for when you want him to propose
The cutest proposal stories captured on video

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