Ask Him: Engagement Overload

maybe he just wants to propose atop a sinking wet mattress?

maybe he just wants to propose atop a sinking wet mattress?

My sister just got engaged over the holidays. I know, I know, everyone got engaged. That’s not my problem. My problem is, I expected MY boyfriend to propose, and feel like he didn’t because they beat him to the punch. Does this mean I now I have to wait for them to get married before he pops the question? Can I bring this up to him without seeming like a total psycho? Am I just a totally selfish person for thinking this way? GAH.

Dear GAH,

I’m not entirely clear on the Girl Code when it comes to stealing a sister or friend’s thunder re: a wedding proposal, and I suspect that your boyfriend isn’t either. And there’s probably no real hard and fast rule, since proposals and marriages are viewed so differently between individuals.

But if he had been planning to propose to you over the holidays, I can see why he would be deterred and decide to hold off; to hide that ring away until a time when your engagement will be, bar none, top of the family and friend social news cycle. He may not have wanted to compete with the future in-laws, especially if he copped you a ring that is much less impressive than the conflict diamond your sister’s fiancé somehow acquired. Dude probably saw your sister’s rock posted to Instagram with the caption “HE WENT TO JARED!!!!!!!!!” and was like “Oh god this is no good. This is no good at all. I can’t compete with this. Not right now. I better sit on this ring until people forget about this huge monstrosity, or until I can take out another loan to buy a better one. I wish I’d watched my credit more closely in my twenties.”

It’s also entirely possible that he has plans to pop the question at a less cliché time to do so. I can understand why people propose over the holidays. It makes sense from the standpoint that you’ll be visiting your family members and can show off your rock and get all kinds of attention from the people you love. But everybody and their mother gets engaged in December. I personally would not propose over the holidays, because it’s not a very innovative move. I’d want to propose at a time, and on a day, that will be special forever, that won’t be overshadowed by other festivities, and other peoples’ milestones. I mean, if you get engaged in, like, July, the picture you post to your social media networks of your hand wearing its newest accessory will not be overshadowed by hundreds of other versions of the same picture with a different set of diamonds and different colors of nail polish.

Do you have to wait until after your sister’s wedding for your boyfriend to ask you to marry him? I would say absolutely not. (This is assuming that he really is already planning on proposing to you.) I can’t imagine a guy putting his desire to snag a fiance on hold while he waits for her sister to plan and go through with a wedding—a process I assume is going to take a year or more. When you want to marry somebody, you should ask when it’s right for you and for your significant other. And that’s that.

Can you bring this up to him without seeming like a total psycho? I personally wouldn’t. At least not yet. Maybe he’s just holding off until Valentine’s Day (which, again: cliché). If it goes beyond that and he hasn’t asked, but you’re very confident he wants to propose to you, then you can bring it up. However, I would do so in a very subtle and sensitive way, a way that won’t particularly scare him or feel like you’re vaguely demanding that he propose to you, but will instead just let him know that you know—hypothetically speaking—you would be fine with making plans to tie the knot before your sister has her special day, that her schedule shouldn’t influence yours.

You should also be prepared for a very weird, awkward and potentially painful conversation if you bring this up and your hunches vis-à-vis his wanting to ask you to marry him are incorrect.

Are you totally selfish for thinking this way? Not really. Just like your boyfriend, you need not put your feelings and plans on hold because your sister is getting married. It’s not like your desire to get engaged somehow takes away from the happiness that (I hope) you’re feeling for your sister.

Good luck in your pursuit of a future husband!

All the best,


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