I’ve been in an on-again/off-again, oftentimes long-distance, relationship with my for-now ex-boyfriend for six years. Right now we have a “when we’re together, we’re together” arrangement and we’ve defined our relationship as open in the past.
Well, things are shifting again and we’re thinking about moving toward being more seriously together, but still long-distance and open. If we decide to get back together, I’d like one of my boundaries for our open arrangement to be that he not sleep with anyone that I know personally. But now I’m not sure if I want to know if he has slept with anyone I know during any of our in-between times.
On the one hand, I feel like I might make myself crazy if I don’t ask and am left wondering. On the other, I once accidentally found out that he did sleep with a friend of mine during a time when we were broken up that also made me feel really bad. What would you do?
— Friends with Benefits
You’ve combined some of the most challenging relationship dynamics: long-distance, open, long-term AND on-again/off-again!? Damn. Something tells me you might be a glutton for punishment, but that’s 50 shades of a different column for another week.
There’s a common Don’t Ask/Don’t Tell “policy” generally popular with folks new to non-monogamy. DADT tells partners “Do what and who you will, but I don’t want to know anything about it.” Though I get the appeal of DADT for non-monogamy newbies, it does little to shield folks from tough feelings. Instead, it sets people up to deny jealousy rather than learn from it, it closes partners off from each other rather than holding open space for others, and these arrangements typically end with everyone in worse shape than if they Did Ask and Did Tell.
Me? I would want to know. When Dorothy pulled back the curtain on the all-powerful wizard in the Wizard of Oz, she found he was just a nice, lil’ shrimp of a man. Meaning, our minds can play some terrible tricks when we’re feeling emotionally raw, downright jealous, and awfully creative; a fleeting thought that he may have slept with a mutual friend can magically become a convincing story about him randomly meeting Jennifer Lawrence at a cool underground party in NYC and having the best sex of his life with her in some glamorous penthouse because JLaw is basically someone you know right because you just loved her in Silver Linings Playbook and now your ex is going to be famous and you will be nothing. Nothing!
In reality, the people your dude has slept with are all real people — with qualities both wonderful and flawed, sex moves both explosive and meh, and their own set of insecurities and relationship baggage. But, if you never peek behind the curtain, you’ll never know this for sure.
Does lifting the curtain obliterate any icks you might feel? No. But, it does give you the information you need to move through it rather than sink permanently into the comparison quicksand.
My advice is to ask your dude the questions about his past and present that give you the nuggets of info you need to move on — Have you slept with our friends?, How often?, Catch feelings? — rather than the self-punishing, indulgent questions that simply sink you deeper: Is her body better than mine?, Can she do X better than I can?
However, if you weren’t together and didn’t have relational boundaries set up at the time, you may just not be entitled to this personal information — as much as you’d like to think you are (sorry). Though Jealousy’s bestie Possessiveness might have us convinced that the rule is “once ours, always ours,” both your dude and his special friends — mutual to you or not — are entitled to their privacy and experiences without shame or guilt. Plus, kicking possessiveness now will take you a long way in all relationships.
Moving forward, make sure you’re both clear about agreed-upon boundaries upfront. This way you don’t get caught off-guard again and he and his partners will know what he’ll be expected to share with you.
Yana Tallon-Hicks is a pleasure-positive sex writer and educator living in the Pioneer Valley. She has a website bursting with sex advice, resources, and workshops at yanatallonhicks.com.