How do I talk to my friend with benefits about safer sex issues?

I have a friends with benefits relationship. I was on the pill before we started this relationship and I had a STD test which was negative. When we got together we used condoms a few times and then we got in the habit of not using a condom. I haven't been with anyone else since I was with him, but he may have. I don't know how to ask him if he uses a condom if he is with another girl or if he has ever been tested. Do you have any ideas I can bring this up in a not nosy sounding or not an accusing way? I just want be safe and I want him to be too.
Heather Corinna replies:

How about something like this: "Hey, I know we should have talked about this before, but since we've been having sex without condoms, I need us to talk about safer sex now. I don't want either of us to be taking risks when we don't have to, or when we should reduce them, so can we talk about this a bit?"

If he says yes -- which obviously he'd better: you don't want to be with someone, even casually, who won't -- then the first thing for you to do is to determine if you're monogamous right now. So, you ask is something like this, "I know we're friends with benefits, so I'm asking this about our health, not out of ownership or jealousy: are you having any kind of sex with someone else right now, have you recently, or do you think you might while we're together?" You can then also disclose your status in that regard, so he knows for his own decision-making that you haven't been with other partners recently. You might also voice if you intend to stay monogamous.

If the answer to either from him is yes, then really, you just want to shift back to always using condoms. If the answer is no, but you haven't yet been together monogamously for at least six months using condoms, then you still want to go back to using condoms.

The safer sex practice we know, and have had proven, works to best reduce our risks is six months of latex barriers use AND monogamy, with an STI test at the start of that period and one at the end. If both those tests, for both partners, come back negative, and both partners remain monogamous, then it's much safer to go without condoms, and STI risks are going to be very minimal. Otherwise? You just can't count on your risks having been reduced. And while you have recently taken risks, in the case that he does have an STI, that doesn't mean it's been transmitted to you yet. So, don't feel like since you took those risks, there's no sense in not continuing to take them, since that just isn't true.

So, if either of those situations exist and you do need to go back to using condoms, then you say something to the tune of, "I know that we went without condoms a few times, but I also know that wasn't very smart of us. So, I need for us to go back to using condoms, every time, until or unless we have been together for at least six months without being with other people, both have new tests that are negative, and then have a talk about if we're going to stay monogamous from a sexual health perspective. If we get to that point, and we both still want to have sex, monogamously, and ditch condoms, we can revisit that option then."

Next up, it's time to ask if and when he's been tested. So, after this last bit of discussion, you can then say, "My last STI test was on [whatever date it was on] and my results were negative, so you know. Have you been tested before? When? What were the results?"

If he has been tested, has not been with other partners but you since he was last tested, his results were negative and the two of you have also been monogamous for the last six months, then I'd talk about not using condoms, if that's something you want to do. If neither of you have had a recent test, I'd just have each of you get one more first, and then you'll also obviously both need to agree to monogamy henceforth. You can agree to just discuss it with each other in advance if you are going to choose not to be so that you can know to go back to condom use should either of you be with someone else.

If he has not yet been tested, then it's time to ask that he please does that, like this,"I'm most comfortable being with someone who has been tested, so that I can know what my risks are, if any. Can you schedule a test for yourself soon? If you're nervous about going, I could go with you and get a new one myself while I'm at it, if you want." Condoms reduce your risks, after all, they don't remove them. Again, I draw a line here: partners unwilling to get tested aren't partners I consider myself to be physically or emotionally safe with, or who I see as being ready for sexual partnership. I think it's a sound line, one that, paired with latex barriers has kept this very sexually active gal healthy for decades, and one I'd encourage you to draw as well.

These kinds of conversations are, of course, a bit loaded, but I find that the more plain and unemotional you can make them, the easier they are. If you set a tone and a precedent that this is about health, not about value judgments, and if the relationship you have is pretty comfortable and known to be what both of you really want, it shouldn't be that big of a deal. If this person is your friend in earnest, it may be easier to have this conversation than it is for people in romances where they haven't developed a friendship yet. If you come to the conversation as comfortably as you can, he's likely to respond in kind.

Obviously, when you're in sexual relationships which are new, casual or nonmonogamous (open), you've got to be able to voice these kinds of things pretty bluntly, right from the start, and I promise, the more you do it, the easier it gets to do. One reason some people only choose to have sex in serious, long-term relationships, or hold off on sex until a relationship deepens is because some folks find it too difficult to be this direct in something casual or very new. Only you can know what your abilities and limitations are in this regard and make your choices accordingly.

Too, and probably also obvious, with most casual or open relationships, latex barriers are just going to be a given, and not something you'll often stop using. In the future, you'll want to try and develop your assertiveness when it comes to insisting on barriers in situations like this, every time, until after you've had these conversations and met the criteria for engaging in sex where risks have earnestly been reduced and will stay minimal.

Here are a few more links to help you out, with communication, relationship modeling, and making choices about safer sex:

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