Oh man, your life is MESSED UP right now.

Not that anyone asked us. But they can officially start.

Send Jilly your questions by filling out the form at the bottom of this post or right here, and she’ll send you a piece of her mind.

Because during those troubled times, it’s always important to ask yourself: What WOULD Jilly do?


My family has always been very close, so it’s important to me to get along with my brother’s new girlfriend (who he, at least, thinks might eventually become his wife). Unfortunately, I can’t seem to have a conversation with her, even about the tiniest things, without it becoming about her. If I start a story about a recent trip, she overtalks me with her experiences about that place, which of course are MUCH more informed than mine (it’s amazing how she’s an expert on everything). If the conversation naturally veers away from a topic she was dominating, she just ignores the shift and keeps talking about herself. She’s constantly dropping little hints about how amazing she is (“which is why my boss is probably going to give me ANOTHER raise”) into her conversation, unsubtly, and is visibly impatient when people start talking about topics she can’t really participate in (read: steamroll). I’m sure she has redeeming qualities—my brother doesn’t have a history of being shallow with women—but I’m having trouble seeing them. Should I warn him against spending the rest of his life with someone so self-centered, or should I bite my tongue … forever?

-Silent Sister

Tell me what you really think of her.

Not that I don’t understand how frustrated you are to always have to play the part of the politely-nodding pair of ears; people who only want to hear about their own achievements, in their own voice, rarely make for interesting listening.

That said, it sounds like, all of your “best intentions” aside, you’re set on not liking this woman. Yes, it’s annoying to be overtalked, but did it never occur to you that, as a person being held up for judgment to a very tight-knit family, she’s in a pretty tough spot? If your brother has told you he’s thinking marriage, there’s a good chance she’s been made aware of the serious nature of their relationship, too. So she’s not just meeting you, she’s got to impress you all, and prove to Team Bro that she’s a worthy addition.

Oof, it’s enough to make anyone have a little verbal diarrhea.

Because—and here again, your lack of slack for this girl needs to be acknowledged—talking too much, and focusing on oneself, is just as likely to be the result of serious nerves as it is a serious character flaw (especially when she’s talking to someone so obviously ready to think the worst of her). Some people clam up in new company; others feel the need to dig into what clique they were in junior year of high school just to fill the silence. Someone in the middle of that spectrum might try to let you know that you have plenty in common by mentioning that she also went to Spain, wasn’t it great?

It could also point to a different, less-temporary kind of insecurity; people who need you to know, from them, how great they are, are rarely convinced of that fact. But again, if this is the case, give the girl a break; it would suck to live inside a head where you only feel like you have value when you can one-up someone else.

I know, it might sound like I’m exonerating her (and blaming you) entirely right now, which may feel unfair, but before you get defensive, keep this in mind: it doesn’t really matter if it’s 100% this girl’s crappy personality and bad behavior.

If you want to keep a good relationship with your brother, and he wants a serious relationship with this girl, you have to just suck it up and try to deal with her, regardless.

Hopefully she does have redeeming qualities that explain your brother’s love for her. But maybe she doesn’t. Whether or not you’d choose it for him, it’s possible your brother is the kind of guy who wants a girl like this for whatever reason. You don’t have to live with her long-term, so even if that thought makes your skin crawl, move on.

And invest in a great pair of headphones and some kick-ass reading material next time she’s coming to a family function.

My roommate always borrows my Tupperware without asking, and puts weird foods in it that leave a stain even after it’s washed. What’s the best way to tell him to stop messing up my stuff?

-Too Many Food Memories

The best way would be to buy him his own brand-new set of Tupperware and write his name on all the pieces with sharpie. Or buy a set for you and give him the stained-but-still-goodies.

Or to realize that it’s JUST FUCKING TUPPERWARE.

Assuming that last suggestion is not an option, make sure that when you present him with his own labeled set, you let him know that you’re aware that you’re the one with a weird hang-up, here, but that you just get weirded out by stains.

Because even if you don’t think you’re being too anal-retentive (you are), this is not the kind of issue worth starting a roommate war over.

Save that for when he eats your favorite yogurt.

You’ve Got Problems (But Jilly’s Got Answers)

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