I know I’m venturing into quicksand here, as this topic is a lot more delicate than some people pretend it to be. The premise seems to be pretty simple: there’s this guy you’ve known since forever, whom you completely trust, who has seen you with and without makeup on, who laughs at your jokes and accepts you for who you are. The answer seems obvious: what could possibly go wrong if the two of you would “get dirty”?

The “Yay”

Reread the first paragraph of this article if you want to convince yourself that sleeping with your best friend is a good idea. I’m not going to list all of those reasons again, but I am going to give you a list of questions for you to linger upon, and if you’ve answered positively to at least four of them, this sex thing could turn out to be a good idea:

• Are you prepared to separate your friendship from your sexual relationship?
• After sex, can you still be objective when your friend confides in you or asks for relationship advice which doesn’t concern you?
• Are you prepared to lay down some ground rules for a successful friends-with-benefits relationship?
• Can you still be open to dating and other sexual experiences despite the fact that you’ll be sleeping with your best friend?
• Will having sex with your best friend feel as natural as it would with some other person you’ve just met?

The “Nay”

By now, you’re probably sunshine and flowers thinking that you’ve found someone awesome to sleep with. But wait, did you consider any of the following?

• Women are sucker for feelings, so you have to take into account the fact that you might fall for this guy (assuming the sex is good), but if he doesn’t reciprocate, then what?
• If you are on a “sex-only” boundary limit, how can you separate friendship from sex? Will the boundaries between these two types of relationships be clear? Not to be a party-pooper, but how exactly will you manage that? Assuming you’re on a night out and have had one too many drinks and got rejected by some rando at the bar, do you A. call your BFF to rant about your night or B. call him to hook up?
• If this sex thing between you two doesn’t work, are there any actual chances of going back to the friendzone with no hard feelings? How would you feel if he started dating? These may seem like futile questions, but from a psychological point of view, analyzing and preparing for all possible outcomes will diminish the shock if one of those scenarios actually plays out in real life.

Here is the deal: sleeping with your best friend is a good idea only if the two of you are opened to the possibility of dating each other. Of course, there is also a happy and rather utopic scenario where you two are just friends with benefits and are super ok with parting ways at some point, but we wary of the feelings and denial trap (which is very likely to happen).

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