Cindy Chupack
Bored in bed? Intimidated by intimacy? Romance running on empty? Have no sexual fear...Cindy Chupack is here!

Q: My boyfriend and I have been together for five years. We have a great relationship. Last year, we bought a house together. I want to get married, but he doesn't ask. He says he wants to get married "someday." How can I handle this without flat-out asking for a proposal?

—Susan, Oklahoma 

A: First of all, congratulations! You're getting married Someday! That's a very popular day to get married among the men I know. A Someday wedding does present problems, the biggest being the planning (of the wedding...and, um, the rest of your life), the second biggest being the creeping feeling that if this handsome, kind, funny, smart man you finally found and fell in love with doesn't get off his butt and propose soon, you might have to kill him.

The good news: Many of my friends have faced this, and most became a Mrs. rather than a murderer. The bad news: If yet another holiday or vacation ended with calls to your family announcing, "We're not engaged," it might be time to give an ultimatum.

"To yourself," my husband says. "What?" I say, annoyed he's reading over my shoulder. He explains that men don't like to be told what to do and that doing so invariably makes them want to do the opposite. (This, I guess, is why he's still talking even though I told him I didn't need his advice for my advice column, thank you.) "If a guy wants to marry you," he continues, "you take all the fun out of it by asking him to ask you. So Susan should give the ultimatum to herself."

"Okay," I concede, "let's say Susan gives herself six months or she's out. Shouldn't she tell the guy?" My husband thinks not. He thinks six months might be exactly what the guy needs to come around, and then—bonus—he gets to feel the proposal was his idea instead of her demand! And if he's not ready, an announcement that she's moving on is stronger than a threat that she might.

"So...blindside him?" I ask. "Okay, she can tell him," he says reluctantly. "But she should be nice. It's what she needs to do for herself, not what he should do."

I know what you're thinking, Susan: "We just bought a house together! Who said anything about leaving?!" But see, the beauty of giving yourself an ultimatum (I'm now a complete convert) is that it forces you to stop wondering what your boyfriend is going to do and figure out what you want to do.

For starters, are you sure you want to marry this guy? Or is it just that you don't want to lose all the years you've invested? And why are you anxious to get married? Because you want to start a family? You're worried he'll leave you otherwise? Or you love him truly madly deeply and want to make it official?

Once you're clear on your reasons, explain to him (in a loving way) why you want to get married sooner rather than later, and maybe he can explain what's giving him pause. Many men have legitimate fears about marriage—of what it means, of not proposing well, of not being able to provide. Maybe you can alleviate some of his concerns simply by talking about them, and vice versa.

Then give yourself a reasonable timeline, whether you share it with him or not. I know it sounds extreme to consider leaving, but if your goal is marriage and kids, and he doesn't want that, it's better to know now. Maybe the sight of you packing (or your absence) will make him realize he loves you enough to commit. If not, he might be a great guy, but he's not the guy for you. And you're on your way to a lasting relationship that much sooner. And—bonus—nobody got killed.

Cindy Chupack is the author of The Between Boyfriends Book (St. Martin's Griffin).


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