The truest statement in the history of relationships regarding whether you should propose or not is also the most vague: “When you know, you know.”

Guys in great relationships or happy marriages know exactly what it means. It means: “I can’t explain it; I just know that when I look at my wife, she’s the only one for me and I want to share my life with her.”

For other guys, the “when you know, you know” phrase translates roughly to: “It’s a crapshoot, pal. You’re on your own with the whole ‘knowing’ thing.” Which leads this second group of guys to ask: “Know what? What the hell am I supposed to know?”

How Do You “Know”?

There is no real answer to this, other than “know” encompasses everything. It includes knowing you love your girlfriend/wife-to-be, knowing that she loves you, knowing that she’s your best friend, knowing that you’re hers, knowing that she’ll make a great parent, knowing that she’ll take care of you, knowing that you won’t mind taking care of her, knowing that among all the other girlfriends you had, this amazing woman was waiting for you the whole time and none of your past ladies could ever compare to her.

To not “know” means you’re feeling the opposite about some of these things. (Hopefully only some — if you feel the opposite about your girlfriend on all of the above, why even bother dating her?Unless she’s Brooklyn Decker — in which case, hang in as long as you can). Fortunately, when you’re no longer uncomfortable, uncertain or “un” anything involving your significant other (most of all, unsure) that’s when you “know.” And when you know, you know, which means it might be time to propose

Be This Guy

Here are a dozen very important things to think about when you get to this point:

1. DIY

Proposing is a man’s game. Period. Ignore the supposedly hip notion that it’s cool for women to propose because of the rise of feminism and the blurring of the gender barrier and all the other tradition-be-damned nonsense. A woman proposing to a man is not hip; it’s lame. I know, I know — there’s nothing “wrong” with a woman proposing. And there may be a few men out there who want to be proposed to (though I’ve never met any). But no matter how progressive and forward your girlfriend may be, there are certain laws in the universe that shouldn’t be trifled with: Women aren’t supposed to open car doors for men. Women aren’t expected to give men their coat if a man catches a chill. A woman shouldn’t have to comfort a man because he’s crying at the end of Love Actually.

And women should not have to get down on one knee and ask for a man’s hand in marriage. Typing that last sentence even felt weird. Men propose. It’s in our DNA. Pure and simple. Guys, suck it up. Don’t be that guy in a group of couples who has to meekly say “My wife proposed to me” when you’re sharing your engagement stories. Everyone might nod their head and smile politely, but every guy at the table will think you’re a towering wimp. Sorry, it’s a fact.

2. Know The Answer

If you honestly have no idea what your girlfriend will say if you propose, don’t ask yet. Think of your proposal the way the late Johnnie Cochran thought about cross-examining a witness: Never ask a question you don’t already know the answer to. Never. By the time you’re ready to pop the question, you should have already had “feeler” discussions about weddings, starting a family, when you want kids, how many kids you want, where you’ll live, income sharing, etc. If you’ve had none of these discussions, then you might want to bring up a few topics to see how she feels. If you’re at a wedding and you ask your girlfriend if she could picture your wedding like this, and she hesitates or gets uncomfortable or doesn’t want to talk about it, it’s OK — having that conversation at someone else’s wedding will be much less uncomfortable than having it on the morning of your own, when your fiancée realizes she said yes because she was just being polite.
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