Handling "Friends with Benefits" Responsibly

I received a request on this topic some a couple of weeks ago, but I had to really think about this one before posting.  I'm presenting here the most general, responsible, safe, and considerate way of handling this situation that I can think of.

The first thing I would like to bring up is the word "friends".  Sure, everyone likes benefits, but friends with benefits are still friends.  You like your friends.  You care about what happens to your friends.  You treat your friends with respect.  I'm purposefully driving distinction between "friends with benefits" and "hookups/booty calls".  If you do not intend to care about how the other person feels or what you do to them, please stay in the realm of casual hookups with other people who are looking for the same thing.  That said, there is no such thing as a "no strings attached" friend with benefits (so get that out of your head) because you both must agree on (and stick to) what kind of friendship and what kinds of benefits are to be exchanged.  You're only in it as long as both people are happy.

I suggest that before you decide to get into any such situation, you really think about what you do and don't want, what you are and are not okay with, what would really upset you, and what would really scare you.  That should leave you little surprise when you do find a friend with benefits and will also help you be more considerate of the other person.  Once you know what these things are, you should remember them and talk about them with your potential new friend.  I know most people would prefer to sweep all of this under the rug, but in effort to be responsible, safe, and considerate, it is better to make sure you are both on the same page.  For example, it is not good to find out down the road that one person thought it was monogamous and the other person is seeing other people.  It's not good if one person thought it was discreet and the other person is talking about it.  You wouldn't want to find out your friend is having unprotected sex with other people the hard way, if you know what I mean.  Be sure to discuss such things early on so that there are no surprises.

So what should you be thinking about?

Emotions.  These are likely to eventually come up on one side or both.  If both people are open to the idea of becoming a more serious relationship in the future (not likely) there is no problem.  However, feelings may eventually arise, most likely only on one side, and the situation is best off terminated before it goes any further.  That should be a pretty solid understanding so as not to drag anyone through anything they don't need.  One good way to keep yourself in check in this area is to keep your eyes open about other people you find attractive.  Flirt with other people.  Keep your options open, even if the rules of your friendship include immediate termination of your current situation if one of you finds another friend.  Being flirtatious with other people can help keep you from getting too attached to any one person.  That said, there is no room for jealousy in a friends with benefits situation.  It is important that you keep in mind that it is not a relationship and you have no hold over the other person.  If they do not agree with the terms you consider important, the benefits should not commence.  If they have already, they should not continue.

Monogamy and Physical Safety.  This is a personal choice that needs to be agreed upon.  For the sake of health, it's a good idea to be clear on rules such as whether the situation is open (it's okay to find other benefits elsewhere) or not.  You should also both really think about what that means and whether one should be using condoms.  I vote yes on that one.  The absolute physically safest way to conduct this business is to have a monogamous friend with benefits, with the explicit understanding that one is to inform the other if they have found other prospects before returning to collect more benefits.  It is important that you trust your friend.  If that's not how you want to do it, just make sure both parties agree.

Time.  It may be good think about how long you would like the situation to go.  If you are moving soon, you might want to mention that.  If you know you can only have such a friend for about three months before you start to get attached, it's a good thing to consider.  If you would like a trial period, that's not a bad idea.  It isn't particularly romantic, but none of it should be or you're really confused.

Level of Involvement.  So how close are you?  Are you just good friends or exes who like to sleep together and know you would be horrible in a relationship?  Do you like eachother but don't have the time or energy for a real relationship?  Are you two people who had a hookup, found out you were good together and would like a regular appointment?  Do you want to do regular friend things together or would you like to just stick to the benefits?  It is really important that both people agree on that last one.  If one person wants a friendship, too, and the other person just wants the benefits, there will be a lot of misread messages.

Accidents.  It's not unheard of for people to become pregnant when they have sex.  What are you going to do?  It takes two to tango, so to speak.  Do you really want to have that disagreement on what the contingency plan is after the fact?  No.  Make sure you're with a like-minded person in that respect.

Termination.  So, how is this going to end?  It is best to make sure that there will be no issues when one person wants to end the situation.  Make sure everyone involved can exit the situation for any reason cleanly, be it because they met someone else, don't feel like doing it anymore, or otherwise.

Why care about all this stuff?  One, the other person is your friend, and a person just like you.  They deserve to be treated with respect.  Two, if you mess it up with one person, chances are other people will hear about it.  A crappy reputation can make it very difficult for you to find more friends with benefits, or friends at all.  Three, you can actually have that person as a regular friend even if it doesn't work out or if one of you meets someone else they'd rather be with.

What do I do if I'm already I'm in a bad situation because I didn't think about all this stuff ahead of time?  Honestly, the best thing to do is just end it before it gets worse.  I'm assuming you already went through and tried to figure out what the problem is.  If it's simple incompatibility of friends with benefits style, end it.  There is no room for desperation here.  You must be more willing to get nothing than to get hurt over it or get it from someone you're hurting.  It's best to approach that person in a nice way, in private (but not at your place) and just tell them that you would like to not continue the situation.  When they ask why, just pick the main reason and avoid making it a big drawn out, dramatic ending.  Keep it nice and civil.  If you're ending it because you found out the other person thinks you're closer than you are, you're best off apologizing for not having discussed it properly early on.  It doesn't matter if you don't think it's your fault.  If it was never discussed and the other person has that impression, it is at least partially your fault.  Take ownership of that, apologize, and end it before it gets worse.

*I had to add this because I was asked.  The answer is no, you should not sleep with that person one last time before you tell them you're ending it.  That applies to regular, romantic relationships as well.  That should be a choice left up to the other person after they already know what's going on.  Try witholding information from your insurance company so as not to discontinue benefits and see what they say when they find out.  I wouldn't suggest suggesting it either.*

If you did your honest best to make it clear to someone that it is over and they for some reason do not believe you, then you have reason to be much more firm and much less personal.  Give that person a week to let it really sink in (in case they're just really hurt) and then read this for inspiration.

I wish you the best of luck in your endeavors.  A good, compatible friend with benefits can be very difficult to find.  If one happens to fall in your lap... just treat that person with respect, whatever you (plural) decide.