Gina Vaynshteyn
September 23, 2014 10:24 am

Ideally, we would be honest with our best friends all the time, but unfortunately, the world doesn’t work that way and we have to pick and choose appropriate occasions that call for bestie wisdom and advice. For instance, if you hate your BFF’s boyfriend because you think she’s too good for him, you cannot simply tell her this. Too many friendships have been compromised because of a guy, so we have learned not to approach this touchy territory. Or if she brings over a fresh batch of chocolate cupcakes that taste like soil, you know you will be dead to her if you say anything short of, “Mmm, these are just so yummy.”  We just don’t say certain things.

However, there are a few very important exceptions, moments that show you are a true, bestest of best friends. And, while we never want to be rude, we always want to have our BFF’s back. Here are some times that definitely call for honesty with your closest friend:

1. When she’s acting a mess

If your girlfriend has gotten kicked out of all the bars, has lost job after job for failing to show up, has started fights with mutual friends for no reason, then you guys should chat. You love her and you want her to take care of herself. This kind of conversation is always hard, but maybe something much larger is going on. Try to get to the bottom of what’s up, and if anything, let her know that you are there for her and you don’t judge her behavior.

2. When her obsession with her ex’s new significant other has gone too far

It’s totally normal to Internet-stalk sometimes. We’re human, and we’re curious, and sometimes we’re inherently jealous. But this shouldn’t go on every day. Being jealous shouldn’t be a part of one’s lifestyle. You don’t want to sound antagonistic, but you should let her know that the sooner she makes a clean break from her ex’s new life, the easier it will be for her to move on and feel happier.

3. If she shows you her tattoo plans and they’re God-awful

She presents you her sketches of a future tattoo that is supposed to “embody” Justin Bieber lyrics as a tramp stamp and you wonder if this kind of “art” could be illegal somewhere. Of course, tattoos are a personal choice, and if your girlfriend wants to get the Biebs tattoo, she can. However, you can still try to dissuade her (Ed note: This is TRUE. We once let a friend get the word “THINK” in bubble letters right above her butt and we’ve never forgiven ourselves.)

4. If she confesses she didn’t use protection with that one dude

This is where you drag her to the drug store and get Plan B while you tell her how irresponsible she’s being and that you love her, but diseases exist, and so do babies.

5. If you catch her partner doing something legitimately suspicious

OK, so remember when I said it’s never a good idea to express your distaste toward your friend’s boyfriend? Well, this rule can be tossed aside if you actually see him doing something that could potentially hurt her. For instance, if you’re out and about and see him snuggling with another girl who is definitely not your friend. Like yes, that will most likely break her heart, but she deserves to know this information before she inevitably gets her heart broken by him down the line.

6. If you ever kept something very important from her

Let’s say you borrowed her favorite cardigan and then left it in a taxi and have been putting off telling her about the unfortunate incident for weeks. You must tell her about the cardigan. You must. She might be pissed, but it’s better to be honest about our screw-ups. Best friends forgive.

7. When you know she’s giving up on herself

If the situation is work-related, encourage her to find a job that compliments, interests, and makes her feel challenged. I think it’s super important to emphasize happiness and fulfillment in this case, since if she’s happy where she is, maybe this talk isn’t necessary. Ask her if she’s happy where she’s at, or would she rather be teaching? Writing? Is there anything you could do to help her? Your job isn’t to judge: it’s to support and encourage a healthy dialogue about her talents and goals.

8. When she asks you to look over her writing

This is so hard to do, especially when your friend is expecting you to say, “OMG this is all so good,” when what you really want to say is, “The introduction needs some work, and maybe you could complicate the protagonist’s character.” However, if you’re not honest, then you’re not being helpful. As long as you’re being constructive, there is no reason for any hurt feelings.

9. If she shows you her resume and it needs work

“Resumes are so fun to write,” said no one ever. Resumes are the bane of every 20-something-year-old’s existence. The cover-letter is the runner-up. These things suck. They really do. When I was applying to jobs straight out of college, I had everyone look at my resume to make sure it was okay. But some people don’t have the chance, and if your BFF is about to send out a resume with grammatical errors or fragments, or sentences that just don’t make any darn sense, well. Get that red pen out. Because you know what? That’s what best friends are for.

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