Why You Should Never Date Your Best Friend’s Brother

Why you should never date your best friend's brother

Why You Should Never Date Your Best Friend’s Brother

Dating your best friend’s brother seems like a no-brainer, right? Your best friend’s an awesome human being, so it stands to reason that their brother would possess many of the same awesome qualities.

Depending on how long you guys have been friends, you’ve probably known their brother and the rest of the family for quite some time already, which makes things a lot easier.

It’s like a life-hack: you already know their family dynamics, their pet peeves, and what kind of pizza toppings they prefer. Much of the awkwardness and uncertainty that usually comes with dating someone new is already out of the way.

But is it really that simple? Are there any downsides to dating your friend’s brother that you might not have considered? Yes, as it turns out, there are plenty. Let’s take a look at them below.

8 reasons why you shouldn’t date your best friend’s brother

1. It could damage your friendship with your best friend

Dating your best friend’s brother could be a total friendship killer. You might think you’re all cool and chill about it, but things can get real awkward real fast if things don’t work out with their bro. Suddenly your BFF is stuck in the middle of a love triangle and that’s not a fun place to be.

2. It will be hard to know where your loyalties lie

Then there’s the issue of loyalty. If your best friend and their brother have a disagreement or a falling out, you might feel like you’re stuck in the middle. How can you really remain neutral when you’re dating one of them? It’s a tricky situation that could cause tension and drama.

3. Awkwardness with the rest of the family

Having been in your best friend’s life for some time, you’ve probably found yourself at the occasional family gathering. If you start dating their brother, those gatherings will take on a whole new level of awkwardness. Suddenly, there’s all sorts of pressure to make a good impression on your beau’s family – pressure that wasn’t there before.

And then you have to consider how uncomfortable said events will become if you guys break up, especially if it’s a messy breakup. Do you really want to be the reason why Thanksgiving dinner is ruined forever?

You might have to end up skipping events you once enjoyed because you don’t want to make things weird or uncomfortable for yourself, your best friend, or their brother.

4. Your best friend might not approve

Not everyone’s cool with their friend dating their brother. Your BFF may have all sorts of concerns and reservations about you dating their sibling – maybe they think you’re not a good match, or that you’re not good enough for him.

The saying, “Don’t poop where you eat,” comes to mind. For some people, they like to compartmentalize different parts of their lives, and having their best friend dating one of their family members could blur those lines in an uncomfortable way.

Ultimately, your BFF’s approval should matter – if they’re not on board with the idea, it might be better to let it go.

5. Can you confide in either of them about the other?

Think about it: your best friend is the person you usually run to when you’re having problems in your relationship. But what do you do when the person causing those problems is their brother?

You can’t exactly go to your BFF for relationship advice or vent about your issues if it involves them directly.

Then there’s the reverse: can you really complain to your boyfriend about your best friend without worrying that he’ll be offended or that it will get back to his sibling?

From their perspective, it might look like you’re trying to turn them against each other.

6. You’ll make comparisons

It’s natural to compare the person you’re dating with other people you’ve dated in the past. But when it comes to your best friend’s brother, you’ll inadvertently compare them to their sibling.

Maybe you like the way your boyfriend does something, and wish his sibling, your best friend, could do it that way, too. Or maybe you’ll find yourself being disappointed that your boyfriend doesn’t have certain qualities that his sibling does.

Either way, those comparisons will eventually start to negatively affect your relationship with one or both of them, as you’re trying to create the perfect human being that has a combination of both their qualities, and that just won’t work.

7. Jealousy

The green-eyed monster has a funny way of showing up in these types of relationships. It could show up in multiple ways:

– Your friend may become jealous of the amount of time you’re spending with their brother and feel left out

– The brother could feel like he’s always playing second fiddle to your friendship with his sister, which could lead to resentment on his part, and tension between the two

– You might find yourself feeling jealous of how close or how familiar your best friend and her brother are, especially if you’re in the early stages of the relationship

8. You can never really move on

In most cases that don’t involve children, when a relationship ends, both parties go their separate ways and don’t stay in contact. A clean break, so to speak. But providing you remain friends with your BFF, you’ll always have a connection to their brother.

Even if you and the brother end things amicably, it’s going to be hard for your friend not to bring him up in conversation. And if you go to any of their family events, you’re going to have to face him again and again. It’s not exactly a recipe for closure or moving on.


Final word

At the end of the day, love is love, life’s too short, and all that jazz. If you’ve fallen head over heels for your best friend’s brother and you’re both on the same page about it, then go ahead and give it a shot. I certainly can’t stop you.

But before you do, take some time to seriously consider all the potential pitfalls of dating someone so close to home. What happens if things don’t work out – will your friendship survive? Only you know if it’s worth taking that risk.