I’m not in a relationship and have been having fun with no emotional attachment but I don’t want to turn people against each other. I am involved with two men that are acquainted. How should I explain the situation to them without seeming callous?

If you’re going for full-disclosure here, which is great, I would suggest sitting each of them down separately and simply being honest. I’ve seen so and so a few times, it is also casual, I wanted to let you know because I know that you know each other and I didn’t want this to cause any problems. 

It’s easy to think that in a NSA* style relationship that it just wouldn’t be worth explaining, but I feel that even casual hands-off relationship have boundaries. Laying down the law will prevent any potential drama these men might have if they were to find out about one another. If one of them isn’t comfortable with the situation, he has the ability to pull out and not share that time with you.

It’s a really difficult question because many people would argue (and can, perfectly well) that it’s your business as long as you’re being safe and respectful. I would say that you’re not obligated to tell them the who-what-when of your other relationships. In the end, you’ve got to feel it out for yourself and do what feels right. That said, the potential break-down from what is supposed to be good light fun is really not worth it, and I’m stickin’ to it. Let everyone know so they can give their consent, or (really) make an attempt to seek out partners who don’t know each other in the future.

Other things I would do when exploring casual relationship:

1. Always make sure new partners are clean, and express to your partner(s) that you and your other partners are all clean.

2. If feelings develop on either end, stop, or re-evaluate the terms of your casual relationship.

3. Define casual so you’re on the same page. Do you call? Text? Spend time together? Or do you just fuck on Saturdays?

The media representation of “I’m just going to fuck whoever I want and not tell anyone and do whatever I want” has never been my style and I don’t endorse it on my blog. I think it’s perfectly reasonable to have a casual setup in which everyone involved understands what is going on and knows that the situation is both respectful and safe. As you’ve noted, things become messier when you add people from a similar social circle. Do your best to handle the situation in a way that you feel comfortable with, in the way that you feel is best. In the end, that’s really all you can do. How they handle it from that point is up to them.

* No strings attached