7 Reasons You Shouldn't Date Your Best Friend

Updated:
Andrew Zaeh for Bustle

Several years ago, I started dating my best friend. At the time, it made perfect sense. We were inseparable, we had so much in common, we were extremely close, and when we realized we had feelings for each other that surpassed being just friends, it seemed almost silly not to date each other. Especially since we were both single and had been single for a while — a factor that we didn't take into consideration as something that was weighing heavily on our decision.

Needless to say, it didn't work out. And, in the process, we lost each other. Now our contact is limited to happy birthday emails.

While dating your best friend or making a relationship out of a friends with benefits situation always works out in the movies, in real life, it's a different story. In theory, it seems like the best idea ever but, in theory, lots of disasters seem like the best idea ever.

Even if dating your best friend does work out in real life, it's still not without its complications. So before you go down that road, here are seven things to consider — seven things that all point in the direction that dating your best friend is a bad idea.

1. Sex Can Change Everything

Andrew Zaeh for Bustle

"Sex changes things and when you date your best friend that friendship changes," New York–based relationship and etiquette expert of Relationship Advice Forum, April Masini, tells Bustle.

As much as we may not want to admit to it, sex can change everything. Once you've seen someone in such an intimate situation, like sex, you never see them quite the same way again. It's because of this that dating your best friend is such a risk.

While dating and allowing yourself to be vulnerable with someone else is always a risk, when it's your best friend you have more to lose, far more is at a stake than just the romantic relationship. You're basically putting all your bets on the table when you date your best friend and when you do that, it's hard to walk away with everything you started out with when you walked into the room in the first place; it's one hell of a gamble. That's also why friends with benefits rarely go back to being just friends.

"If the relationship fails, you’ve lost your best friend and that person is now your ex," Masini says. "Tread carefully."

Or tread not at all, if you know what's good for you.

2. You Could Lose Your Best Friend Forever

Andrew Zaeh for Bustle

If you've ever broken up with a friend, you know it's just as painful — if not more so — than breaking up with a partner. Now think about losing your partner and you best friend forever because you the two of you decided to give a relationship a try. Isn't the thought alone painful enough? It's definitely not a loss many people would want to risk experiencing, because it's double the pain.

"If you date your best friend, you’ve crossed a line and if things don’t work out, you’ll never get your friend back," Masini says. "Things will be forever changed. If you’re not a risk taker, this is one you should avoid."

While in the moment you might be able to convince yourselves that you're making the right decision and it's going to work out, it's important to weigh the pros and cons, and weigh them realistically. Even if you are a natural risk taker, is this a risk worth taking? Are you willing to, literally, lose it all? No matter what your physical chemistry might be saying, it's important to step outside the scenario and see it clearly. Once you sleep with your best friend, you're heading down a road with no U-turn.

3. You Don't Vet Them Like You Would Others

Andrew Zaeh for Bustle

It's far easier to spot red flags early on in a relationship with someone who isn't your best friend. With our best friends, we tend to make allowances for them and let them get away with things that, no way in hell, we'd let others get away with when it comes to dating us. Because of this, you won't see the glaring red flags.

"Your best friend may fly under the radar you typically use to vet dates," says Masini. "In other words, because someone is your best friend, you don’t filter them the way you’d filter a new first date."

While you might be able to dismiss this by telling yourself that you know everything you need to know about your best friend now partner, there's a distinction that needs to be made: being just friends and dating someone reveals different sides of people. You may know your best friend like the back of your hand, but you don't know what it's like to date your best friend.

"When you don’t know someone very well, and you start dating, you’re usually more careful and you don’t let things slide the way you do when your best friend is now your date," Masini says. "It’s not until you’re deep into the relationship you realize that you let someone in who doesn’t share your values as a partner."

4. Your Best Friend Knows You A Little Too Well

Andrew Zaeh for Bustle

When I first started sleeping with my best friend, before we "officially" started dating, my therapist would tell me over and over again that you're not supposed to know what your best friend looks like or sounds like when they orgasm. She definitely had a point there. Also, the flip side of that is that you may not want the person you're dating to know the details your best friend knows.

"Your best friend knows too much," says Masini. "They know who you’ve got a crush on. They know who you may have had an affair with. They know all your deepest, darkest secrets. This is a tough premise on which to build a romance."

I mean, does anyone want to start a relationship already knowing everything there is to know about their partner? Wouldn't a little mystery do a new relationship good? Granted, you'll get to see another side of your best friend, like how they are as a partner, but there's still so much that's already been discovered and it's that fact that's worth considering.

"Typically, a partner learns these secrets in a different way," Masini says, "not as a confidante, but as someone new in your life with whom you’re sharing to create intimacy."

5. Being Best Friends And Being Partners Is Very Different

Andrew Zaeh for Bustle

I'm currently in a non-relationship with a friend, who's technically a friend with benefits with whom I've fallen in love. Like that isn't a disaster waiting to happen or anything. But, in addition to knowing that we've created one hell of a mess, I also know that our compatibility as partners versus our compatibility as friends are in completely different stratospheres. For the most part, he is not the type of person I would ever want to seriously date and I'm pretty sure he'd say the same thing about me — despite the mass amount of sexual chemistry between the two of us.

However, sometimes when you start dating your best friend, you assume the friendship compatibility will automatically cross over to the partner compatibility, but that's not always the case — if ever the case.

"Best friend compatibility is different than partner compatibility and your best friend may be masquerading as a great date — because you’re not running each other through the dating gauntlet," says Masini.

Basically, you think you're getting the real deal, but you just might be getting what your best friend wants you to see in the moment. The problem with that is that no one can keep up a charade forever.

6. You No Longer Have A Best Friend To Turn To

Andrew Zaeh for Bustle

When you're dating your best friend, exactly to whom are you supposed to turn when the person you're dating is being a schmuck or giving you a hard time? It's going to be really awkward to confide in your now-partner about all the things you'd confide in a best friend.

"If things don’t work out, you can’t seek comfort with your best friend — because they’re the one with which things didn’t work out!" Masini says. "Your best friend may be your comfort and your solace in times of trouble, but if you date your best friend and things don’t work out, you’ve lost that resource."

So now what? Seriously; on whose shoulder do you cry and whose phone do you blow up with texts of complaints and disbelief? Definitely not your best friend, because they're no longer just your best friend!

"You can’t go to your best friend to talk about a fight or a break up in the same way you used to," Masini says. "You may not have anyone as valuable as your best friend was to you in this situation."

While you may have other friends to whom you can turn, no one is quite like your best friend. That's just basic math.

7. You Could Find Yourself In A Jealous Mess

Andrew Zaeh for Bustle

When we find ourselves in too many relationships — friendship, romantic, or otherwise — drama almost always follows. With drama, comes a whole slew of emotions, especially ones that you may not have felt before you found yourself in such a mess. One of those feelings is jealousy.

"Since you turned your last best friend into your current romantic partner, could your enthusiasm about a new best friend be a threat to your romantic relationship? There is definitely a logic to that," Masini says.

There's also the possibility of having created a new pattern of turning best friends into partners. As Masini points out, once "you take a dip in the best friend pond, this may be a one time thing — or the beginning of a pattern." So you need to decide how you're going to navigate the possibility of starting a habit that, may or may not, be bad for you (not to mention all your other relationships), or if this really is never going to happen again; if this friendship-turned-relationship is just a one time deal. If the latter is the case, then you need to figure out how you're going to keep the status quo with your new best friend and let your partner know they don't need to worry.

Although whom you choose to date or not date is 100% your choice, when it comes to dating your best friend, there are some serious factors to take into consideration. While there is a chance that you can live happily ever after, it's just a chance and some chances aren't worth taking.

This post was originally published on March 23, 2018. It was updated on June 4, 2019.

This article was originally published on