Dear Just The Tips,

Two of my out-of-town friends/lovers are coming to my city the same weekend, and they both want to stay with me. One of them I’ve been planning forever because he’s coming back from school, so I guess he gets to spend the night, and I’ll spend the afternoon with the other? The only thing is, I’m actually a lot closer with the other one, but I see him more often. I’m conflicted. Help! How do I mitigate this?


My Dearest Doublebooked,


What a fabulous problem to have. I’m notoriously bad at scheduling pretty much everything, so I admire your ambition in the realm of the logistics of love. Perhaps you should be giving the rest of us tips.

Your quandary has a particularly modern flair to it, which I appreciate. It sounds as though you are trying to be conscientious about your involvement with multiple partners and to schedule your time ethically.

Photo via Amazon

Photo via Amazon

To assist you (and me) I’ve turned to another expert—Dossie Easton who has been a practitioner of free love and ethical sluthood for 50 years. She decided to commit to five years of non-monogamy shortly after her daughter was born. As she puts it, “I took my whole reality apart and put it back together. I told myself I would be non-monogamous for five years. The fact that I am who I am was by 1950s standards a ‘wrong woman.’ I am too smart, too, and I do not get my rocks off by washing somebody else’s socks.”

Easton co-wrote the book The Ethical Slut in 1997 and followed it up with five more volumes on the arts of love and sex after that. I can think of nobody better equipped to answer your question with savvy and grace than Ms. Dossie! Onwards.

As Dossie and I were discussing your question we found ourselves wondering whether or not these two lovers knew about each other. When I pressed Dossie on the ethics of that she asked, “Is this a full-scale negotiation where all people get to voice their opinion? If so, one of the partners might say, ‘You need to choose.’ Then she can freely make a choice, given her desire.” Putting all your logistical cards on the table might help you make a clearer decision in good conscience.”

Dossie suggests you ask yourself two big questions:

What do you think is fair?

What do you want?

In her book Easton goes on to say, “Forget about fairness. Ethical sluttery does not mean that all things come out equal. Different relationship have different boundaries, different limits and different potentials.”

I’m inclined to agree with her that in the long run getting too preoccupied with fairness will lead you to unnecessary feelings of guilt, resentment and some weird kinds of tallying when it comes to love and sex. However, considering your own and other people’s boundaries via those two big questions above will certainly give you some major perspective.

“Presumably this is not the only weekend they’ll get together,” Easton reminds us. “I always tell couples who are going to a play party for the first time, ‘Do not go to a play party acting like it’s the only play party they’ll get to go to ever. Make agreements and test them out one at a time.‘” This same might be said of this particular scheduling arrangement. You can start to feel like the situation is more urgent than it really is if you lose sight of the fact that you’ll probably get a chance to see both these guys in the future. Unless you really won’t get to see one of them, in which case, I’d say hang out with him.

If you do have to disappoint one person it’s good to make it up to them in the future. “I would look for something special for the person who gets shorted–a fabulous Sunday brunch or rent a dungeon for the afternoon!” Ask yourself what would make the other person feel great, then do that.

As Dossie says, “We need to let go of the idea that we are supposed to make a right/wrong decision. These are not questions of good and evil. You need to figure out what’s good for you to do. This is not a moral issue. This is a difference of opinion.” Take yourself out of the moral hot seat and start framing this as purely logistical.

Dossie reminded me that one of the lovers might be willing to step aside. What a delightful thought. She then went on to relay a story of a time with she was living with two single moms, and they would alternate who babysat and who went out. “One day,” Dossie told me, “one of my lovers showed up and offered to babysit, saying 'You guys go out dancing. I’ve got this!’“ The story reminded me that people are often more than willing to meet your needs.

My dear Doublebooked, I hope Dossie’s thoughts on boundaries, communication and the possibility of a positive result have mitigated some of your scheduling woes. I have a feeling this sticky situation will only end in double the pleasure and double the fun.


Just the Tips is’s weekly advice column, with professional matchmaker Katherine Cooper. Have a question for Katherine about sex, love or dating? Shoot her a note at