As someone who’s been in a successful open marriage for 6 years, and was raised by parents in an open marriage (although I didn’t know that until I was in my late teens), let me just add that the *first *person you have to be honest with is yourself.
You need to be certain that YOU are OK with dating multiple partners. I mean, it seems obvious on the surface - more pussy? Great! Where do I sign up? But are you willing to devote time and energy to calling three women every night to see how their days went? To juggling holidays among three families besides your own? To dealing with (perhaps temporary) hurt feelings, misunderstandings, bruised egos and bumped ideals from three different women?
Are you honest enough with yourself to stop and listen to that little voice which tells you you’re about to violate a previously agreed upon boundary (no exes, or no friends of hers, for instance?) or are you a “swept up in the moment only to have regrets the morning after” type of person?
Are you alright with each of them dating other men? Really alright with it? What does “dating” mean to you? Are you OK with her (them) disappearing after dinner for long phone calls with other men? Leaving you sitting home alone on a Saturday night while she’s out on a date? Are you ok with each of them sucking other men’s cocks? What about vaginal sex? Anal sex? Goats? Where are *your *boundaries? And can you communicate them to her (them) without getting all goofy and vague, and do you trust her (them) to honor your requests?
Think about safe sex and what you’ll all do with any diseases or children that might come along. If you have one or more life partners, or other people who are short term lovers, then there’s more than just you involved in child support, custody and childcare issues. How will you handle it if one of your lifepartners comes home pregnant and you may not know if the child is yours biologically? If you get someone pregnant, how much involvement do your lifepartners expect to have in that child?
Finally, how “open” do you want to be to the rest of the world? Will your friends know? Families? Coworkers? I can’t tell you how many people have gotten all flustered after seeing my husband kiss another woman, and have come up to me all tizzy-fied to let me know “what’s going on.” (Interestingly enough, no one’s ever done the same for him after seeing me kiss another man!) We’ve found it easier to be a bit vocal about our openness, as it reduces that sort of social drama. But we’re also in a rather counter-culture social group where it’s not so unheard of. (Still, 98% of our friends are monogomous.)
Think long and hard on all these, my friend. Only once you figure out where your own heart and ideals lie can you really approach other with any clarity and honesty.