7 Reasons You Shouldn't Date Your Best Friend

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 awhile — 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 workout 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

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

As much as we may not want to admit to it, sex can change things. That's also why friends with benefits rarely go back to being just friends.

2. You Could Lose Your Best Friend Forever

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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 best friend forever because you became partners; it's definitely not a loss many people would want to risk experiencing.

"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," says Masini. "Things will be forever changed. If you’re not a risk taker, this is one you should avoid."

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

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It's far easier to spot red flags early on in a relationship with someone who isn't your best friend, because you make allowances for your best friend and let them get away with things that, no way in hell, you'd let others get away with when it comes to dating you.

"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. 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. 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

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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. Typically, a partner learns these secrets in a different way — 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

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

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

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

7. You Could Find Yourself In A Jealous Mess

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"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," says Masini. "When you take a dip in the best friend pond, this may be a one time thing — or the beginning of a pattern."

Although whom you choose to date or not date is 100 percent 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.