Dear Captain Awkward,

Context: My sister and I are incredibly close and talk about everything. We grew up in a Charismatic Christian home. We’ve spent a long time trying to work out The Right Thing, first as Christians, now on our own. These days we’re both happier, but it’s still difficult trying to figure out if I feel guilty because the situation warrants it, or if it’s a hangover from religion.

Current day: We live together, we’re both bisexual and poly. My sister is currently seeing a small group of lovely people who’re all involved with each other. I haven’t been in a polyamorous relationship to date, but I also identify as poly.

One of my sister’s partners and I have had some flirty chemistry for a while. Over the holidays that went from light physical affection to an enjoyable makeout session. (My sister knew about us getting handsy and kissing btw).

Now my sister and I are discussing the possibilities of whether I should date him as well, and what could happen as a result. We’ve tried to cover all the bases (it’d be awkward if one of us stopped seeing him, how the group would handle it, who goes to parties with him, etc) and are currently at an impasse.

Neither of us wants to police the other’s behavior. She won’t tell me I can’t date him because she doesn’t feel that’s her right and she wants me to be happy. I don’t want to date him if it’s going to cause any harm or hurt to our relationship or her relationship with any of her partners.

To add more context, this isn’t the first time someone has been interested in both of us, (though we’ve not yet dated the same person). It’s ranged from more emotionally complex (her ex-husband, an ex-boyfriend) to a guy we got to know at different times. We have similar tastes in a lot of things and we get along very well, and people are drawn to that. (We also both have anxiety over everything, be it big or little, lol.)

I desperately don’t want to hurt anyone here, mostly my sister. I know I have a tendency to shut things down before they have a chance to develop, partly out of self-preservation. Realistically I know this won’t be the last person I have chemistry with and it won’t kill me not to date him. At the same time, it’s been a while since I’ve been attracted to someone and enjoyed being around someone this much.

I also don’t want to not take a risk simply because it’s unconventional or complicated.

Any advice is muchly appreciated.

Anxious Sister

Dear Anxious Sister,

You made out with this guy and the world didn’t end.

Laurie loved Jo and then married Amy and the world didn’t end. Supernatural fanfiction which I am NOT linking here happened…and the world didn’t end.

You know and I know that if you both date the same guy at the same time, some people will make jokes about sister-wives and speculate awkwardly about threesomes. And some people will find it forever icky. Right or wrong, appropriate or not, true or not, icky or not, only you and your sister and this dude have to live with the potential awkwardness, so only y’all get to decide how much you care and who you tell and how you live with it.

The world won’t end, but there are a couple of things in your story that give me real pause:

Y’all made out before hashing out the feelings & ethics part with your sister. If he initiated said make-outs, was he absolutely clear on whether your sister was cool with it? On whether you were? He’s sexy, yes, but is he a good person? Does he see you as a person separate from your sister or is this like in Civ 5 when you use Great Generals to annex a neighboring state’s territory a little at a time? More importantly: “It’s a free country, I can’t tell you what to do” is not the same as “I think it’s great and you should do it!” If your sister enthusiastically wanted this to all happen, wouldn’t she say so? To me, “we’re at an impasse” means “nope.” Just because everything used to be off limits in your home growing up it doesn’t mean that everything has to be within bounds now or you are somehow falling prey to convention.

Good news: The world is full of people, many of whom will probably want to joyfully explore sexy-times with you. Whether you ultimately pass on this guy or decide to make an interesting mistake, maybe 2017 can also be the year you do some fun sexual exploring on territory your sister has not scouted first.

Parting jaunty musical number, because a) I fucking love this weird-ass movie and b) the world hasn’t ended (yet).