8 Uncomfortable Things You Should Be Talking About With Your Friends

Race because it’s long overdue and completely insane to ignore any longer.

Now is the time. Each of your friends has a different relationship to race and discrimination and otherness. Know what that is. It’s important. Listen and learn from each other. Ask questions from a place of allyship and answer them from a place of friendship. If it feels vulnerable and uncomfortable, you’re doing it right. It’s not enough to be actively engaged on social media; we must be actively engaged with real human beings in real life.

Money money money.

We spend more time actively ignoring socioeconomics than we do acknowledging it. Flip that dynamic. The truth is, almost all of us have experienced some form of money problem because money has a habit of creating problems. From family to student loans to unemployment, money is not invisible, as much as we may wish that to be true. Know if your friends have specific boundaries or considerations. Only then can you respect them.

Loneliness in times when we outwardly don’t seem lonely at all.

It’s possible to be lonely in a room full of people and a city full of things to do. It’s possible to be lonely in a family or friendship or community. Loneliness does not stem from the lack of bodies and stimuli. It stems from the lack of a sense of belonging. From the outside looking in, it might seem like you’re busy and flourishing, and it might feel silly to admit that you’re actually lonely. Name it. Say it out loud to one friend who you love and trust. Dive in and unpack it together. Observe as it begins to ebb away.

Expectations (which are not only reserved for your partner).

Friendship feels like magic sometimes, in the way it seems to build and grow and take on a life of its own. Contrasted with dating and romantic relationships, friendship can feel wonderfully, refreshingly simple. No big moment to define “what you are” and no need to discuss exclusivity. This lack of structure and absence of commitment ritual makes it uncomfortable to discuss expectations. Know that you’re allowed to have them. You should, in fact, have them. Friendships are meaningful relationships into which we pour our time, our energy, ourselves.

Feedback and getting to that 2.0.

Working in a corporate office, or even a startup for that matter, gives “feedback” a bad reputation. It’s often awkward and poorly constructed and even worse delivered. But the reason companies try so hard to build a culture of feedback is because that’s how we grow. Why is it that we rarely think to ask our friends for feedback? They’re people who know us better and differently than our colleagues. Forget professional development here – use them for personal development. Name a thing you’d like to get better at, and ask them to help you along the way.

Regrets that we’d rather completely ignore and hide from.

Nobody is perfect, but sometimes it’s nice for people, even our friends, to think that we are. We often categorize our regrets into two columns—things that feel “on brand” for us, and things that bring us shame. The former makes it easily into conversations over brunch and on walks around the park. But the latter is probably more worth examining. The next time you find yourself sweeping a mistake under the rug, ask yourself why you’re doing that. And if you need a soundboard to help you figure it out, there’s undoubtedly one just a phone call away.

Sex—not just the good and the bad but the ugly.

OK, friends do talk about sex. Probably a lot. But we tend to stay in the lane of light and fun and funny. Relationships, marriages, and divorces are fraught with sex issues. And it’s that level of sex talk, the kind with that weighs heavily and relentlessly, that we often carry by ourselves. This might come from a place of embarrassment, or it might come from a place of not knowing where to start, how to normalize this conversation. But there’s no big secret. It normalizes one coffee date, one cocktail hour at a time.

Evolution and friendships that needed to end… yesterday.

Unstructured beginnings can lead to unstructured endings, ripe with potential for chaos and drama. It’s a fact of life that we outgrow friends, and it’s not necessary to give in to the passive aggression that might surround it. Be the person who acknowledges your time and growth together. Be the person who thanks if thanks are in order or apologizes if apologies are in order. A conversation can make the difference between a swirling grey storm of ambiguity, disappointment, and confusion, and the blue skies of moving on.