The first time I had sex with my friend Mad Max, he told me that he loved me. Seeing that I was madly in love with him, I quickly agreed to be his FWB (friend-with-benefits). As I’m sure you can imagine, it was a tumultuous affair from the very beginning, and it didn’t end well.

It was painful.

It was pathetic.

It was totally avoidable.

If Mad Max and I had stopped for a moment, worked through what we really wanted, and followed a few simple rules, we would have been able to walk away from what became an ugly situation before it even started. But, since my debilitating experience with Mad Max, I’ve had many ongoing, enjoyable friends-with-benefits relationships.

While I understand this type of agreement isn’t for everyone (i.e. clingy and/or jealous people come to mind), it may be something worth taking a look at with the right friend if you follow these no-nonsense guidelines.

Pick the Right Friend

The concept of friends-with-benefits is basically enjoying a sexual relationship with someone you consider a friend. In some cases, two people may add sex to their current friendship. In other cases, it may involve building a friendship after starting as lovers. I’ve known both models to work well provided the right person is chosen.

The key components seem to be finding that perfect blend of hot, lustful, ongoing sex with a person you respect enough to treat him or her well. There are other types of relationships - f**k buddies, one night stands, and random hook-ups. These are far different from actual friends-with-benefits.

In addition to needing chemistry, communication, and respect, another big piece to the puzzle is that you're both looking for a similar level of commitment. Attempting to morph a FWBs relationship into a boyfriend/girlfriend relationship is not only manipulative and dishonest, but it’s also probably going to blow up in your face.

Why Not Date Just Each Other?

In some ways, the type of person who's right for a FWB relationship with you is probably similar to the type of person you would date. It just so happens that for whatever reason, dating isn't in the cards. Quite often, one piece of the puzzle is preventing you from taking the relationship to another level. One of you may be dealing with a recent issue, such as a break-up, death in the family or new job, making adding a full-blown relationship to the mix out of the question for now.

Other people choose to join forces as FWBs (as opposed to long-term, committed relationships) because they live in different cities, have current time constraints, or have small children living in the home most of the time. Some people are lying to you. Some people are lying to themselves. And some of us simply prefer non-exclusive relationships over exclusive ones.

7 Questions to Ask Before Getting Into a FWB Scenario

Before you begin the “Are You a Good Match for a Friends-With-Benefits” quiz, have a specific friend in mind. All answers can be answered TRUE or FALSE. Here are the eight questions:

  1. I'm hoping my FWB relationship will morph into a committed relationship.
  2. Once the sex is over, I'll still want this person in my life.
  3. If my FWB met someone special, I'd be happy for my FWB partner (even though I might miss the sex).
  4. I'm interested in finding out more about what turns me on without worrying about the relationship heading south because of my sexual curiosities.
  5. I'm horny and willing to do this with almost anyone (or I believe my friend is in this situation).
  6. I have specific kinks that I want to explore with a safe, trusted friend.
  7. We both have something to gain from this arrangement.
  8. I can be honest with myself around this person as well as be honest with this person.

If you answered No.1 as FALSE, you are starting off on the right foot. Statistically, being in a friends-with-benefits relationship is not a gateway arrangement. It's a relationship on its own terms with its own value. Treat it as such.

Obviously this can change, but if you go into your FWB valuing the person at least enough to believe you will answer No.2 TRUE, then once again you are on the right track in terms of meeting the FWBs standard. If this answer doesn't ring true for you, then a f**k buddy would be a more suitable option for you and the person you're considering.

Let's hope that you answered No.3 as TRUE. Why? Because you value this person and want him or her to be happy. More often than not, these kinds of relationships are short-term because one of you meets someone to date in a more traditional, committed manner. Wish your friend-with-benefits well, and he or she will become your best wing-person.

Personally, I'd love to hear how many of you answered No.4 as true. It's designed to be answered TRUE, but I'm curious how many people see the benefit of a FWB for this purpose. Way too many times when I hear from married men who want to have sex with me, it's because they're afraid to talk to their wives about their particular kink or fetish. If you're curious about something, trying it out with a FWB is a great chance to see how it works for you and another lover. Seriously. Bring that lube or toy into the bedroom. Strap on that dildo and peg him like you mean it. Try anal sex. Try group sex. Try watching (or taping) porn. Try anything you're curious about and see where it takes you. It's downright silly not to at least try.

Question No.5 should be FALSE. I might take a lot of flack for this, but if just anyone will do, then why your friend? Pick the dude down the hall or the woman at the end of the bar. Invest in a Fleshlight or some other contraption that gives you the physical sensation you seek. FWBs is more about the connection between people who genuinely care about each other. Get off some other way if an orgasm's your sole end goal.

Question No.6 is a more advanced version of question No.4. In other words, you know you're a kinkster (or you know you're curious), and you're interested in seeing how your friend likes exploring new sexual options with you. Sometimes this means taking your FWB into new environments where you're a mentor, or you know you're going to be the mentee, so you make the request to be invited as a guest. This is a terrific reason to get involved in a friends-with-benefits relationship because trying new fetishes and kinks is scary for a lot of people. Having a trusted friend who will not judge you as you test your sexual waters makes the situation a lot more enjoyable.

Sex changes things in any relationship. If we can accept that No.7 should be TRUE, then it's important to have each of you benefiting as your relationship changes course. That doesn't mean you have to have the same needs met or that the balance of power won't tip from time to time, but if you're in a position where you're not having your needs met by your FWB (or you cannot have them met by the person you're considering), then you need to communicate more effectively or walk away.

I'd argue that if you cannot answer TRUE to question No.8, then you should walk away from the situation. Don't go into a FWB in order to be manipulative. Don't do it to be selfish. Do it so both of you can experience semi-no-strings-attached sex you both enjoy. I could not answer No.8 in the affirmative with Mad Max, so I should've ended it then and there. Instead, I lied to myself and to him. This is a bad idea on so many levels. If you even slightly lean toward FALSE on this question, abandon ship!

* * * I'm very aware that the Hollywood version of friends-with-benefits is of two people who are great together as friends, then they have amazing sex and then, VOILA, they both realize simultaneously they're a match made in heaven. The sooner you let go of this fairy tale, the easier it will be to see the real value in a friends-with-benefits relationship: You're not dating and that freedom gives you both a chance to explore new, exciting sexual options in a more accepting environment.

After all - you're friends!