"I have recently gotten to know myself well enough to accept that I am a bi woman. At the same time, my husband and I decided to try polyamory. What recommendations do you have for flirting with women (something I've never intentionally done before) while wearing a wedding ring?"
I've been taking my ho prowess all around the country this month! First to the annual Naughty in Nawlins swingers' convention in NOLA, and now to Portland, OR, where I'm shooting content for Yanks.com, stripping it all off at Devil's Point, and teaching people how to do the sex at She Bop. In fact, this week's question comes from one of my awesome She Bop workshop attendees!*
*Note: I specifically requested that said attendee submit this query to my column. I didn't feel qualified to answer it on the spot, as I've never been married, so I opened the question up to my beloved community of polyamory experts. I've combined the best of the [paraphrased] responses with my own observations and opinions. A major "thank you" to everyone who contributed their labor!
In my flirtation classes and coaching, I often speak to something I call "leading with awkward". This is the practice of identifying what we are feeling insecure, shy, self-conscious, or uncomfortable with pertaining to ourselves, then naming it out loud in order to ensure that we retain power over it.
Here's a non-sexual example: Imagine that you're running late for a party being thrown in your honor because you've been desperately trying to cover that enormous, erupting pimple on your forehead (hey, adult acne is a bitch!). Your imagination is already churning with folks' horrified reactions to it. If you arrive at the party and spend the entire time wringing your hands and avoiding eye contact, terrified that someone is going to point out your blemish, you're disempowering yourself (and robbing yourself of a perfectly good party!). Instead, if you stride confidently into the party and immediately snag the arm of a friend, rolling your eyes while gesturing to your forehead and loudly lamenting, "Can you believe the timing of this monstrosity? The nerve!", you've immediately put the ball in your court.
In your specific situation, your wedding ring - as well as your new sexual orientation as a bisexual woman - are your "pimples", although that doesn't mean you need roll both of them out at the same time. I would recommend using the wedding ring first as a lead-in to talk about polyamory. Make eye contact with a hot woman, make a gentle but pointed approach, and - assuming you're in a bar-type setting - offer to buy her a drink.
I'm recommending being more bold as a way to set yourself up for success. I happen to know - from meeting you - that you identify on the more feminine side of the spectrum. There is a nationwide epidemic of feminine women having difficulty hitting on other feminine women, largely because of how AFAB (Assigned Female At Birth) people are socialized. We're told to accept advances, not initiate them. We're taught that we're the vessels, the passive ones; that we get partners by being demure, not forward. As such, I've attended sex parties that were exclusive to femmes, and I've watched a dozen or so gorgeous women sit around in a painfully-quiet circle fidgeting with their hair and asking each other where they got their shoes from. It's fucking maddening.
The point of me saying this is that oftentimes hitting on femmes AS a femme is incredibly confusing and challenging, and not just for the noobs, so be kind to yourself. By crossing the room to make that initial approach yourself, you're already making an impression and setting yourself apart. Here are two possible ways of elongating the interaction:
After introductions, tell an anecdote or make an observation about the venue that makes her laugh and/or relate to you. Admit that that's your cliche and inexperienced way of flirting with women, and explain that you're new to the scene because you and your husband recently opened up your relationship. Wait for her to react or respond, then lightheartedly offer her the opportunity to decline if that sounds like more than what she was bargaining for. Follow up with, "But if you ARE interested in some company while you drink, I'd be interested in getting to know you more."
After introductions, tell an anecdote or make an observation about the venue that makes her laugh and/or relate to you. Then throw something out there like, "Boy, it feels weird to be flirting with a wedding ring on!", or "I bet this gay bar doesn't see a whole lot of women with wedding rings in it!", or something less flippant and more vulnerable, like, "Oof, can I admit something to you? This is my first time out cruising with my wedding ring on, and it's totally tripping me out!" Then segue into discussing non-monogamy.
If she's interested, let her take the lead in the conversation, and make sure you clarify any boundaries or intentions that would be pertinent for her to know, i.e. if you're looking for casual sex only, if you're looking for a committed female partnership, etc.
"I'd start with a reminder that queers can get married too, and even when it wasn't legal we've been having ceremonies and wearing rings. So on the surface a ring doesn't say anything about the gender of your partner. On top of that, it's true that queers are less familiar with wedding rings, but that also means very few people scan your hand for a wedding ring or make assumptions about what it means if they see one. I wore a wedding ring for about a decade and only ever had someone notice and mention it maybe 3 or 4 times -- and never when I'm flirting with someone."
"Definitely find a group of like-minded people, whether that’s an explicitly queer space or an explicitly non-monogamous one. If you can’t find any, consider starting your own! It's easier if you get to make some friends. I would rarely try flirting with a woman if I didn't know she was either gay or bi and somewhere on the non-monogamy spectrum. Meetups, munches, these are all good gatherings for building relationships. But take your time. I flirt a lot. All the time! And I'm not convinced the signals quite work the same way with women."
"If she's interested in dating lesbians, I'd tell her she may want to prep for a little burn. Right or wrong, a lot of gay women could have strong negative reactions to being hit on by a bi-woman who is married to a man. One time I was on a first tinder date, and she found out that I had been married to a man before, and she reacted pretty strongly... she went on a tirade about how so many bi-women expect you to pick up all the tabs and do all the work in bed (My tinder profile didn't explicitly say bi at the time so she was surprised). I was patient with her concerns, so it turned out fine. It's good to have perspective on what people might have been through or why they might be suspicious of married bi women."