A 30ish Manhattanite wrote to us with a conundrum typical of non-monogamous relationships—in fact, we have several versions of this same question in our inbox. “My boyfriend and I have been together a few years. We love and are committed to each other, but we also want to sleep with other people. We decided to try having an open relationship, and we created OKCupid accounts. The thing is, I’ve found it ridiculously easy to meet men, and he’s having no luck at all. He’s had a few dates, but they’ve just been awful. Meanwhile, I’ve got more than I can handle. It’s created a lot of tension, and I’m putting a hold on my own adventures for now, even though I don’t want to. What can we do for him?
A woman in her 20s from the Bay Area asks, “Have you ever seen people successfully use upcoming OKCupid dates as a negotiating tactic to get someone in real life to date them? I know it sounds like a terrible idea, but maybe if done right it could move someone from the friend zone into the dating zone on a semi-subconscious level by sparking their interest and making them realize it’s a now or never type opportunity?”
A 26 year-old Brooklyn woman writes, “I love that I’m surrounded by so many smart and ambitious women in New York, but unfortunately that means we’re all in competition for the same six manchildren. The dudes on OKCupid (and maybe NYC?) are flaky as hell, and I’m tired of having a few great dates where things click, and then nothing. I sort of suspect that the only way I’ll end up in a good long-term relationship is if I leave NYC. I’d be very curious if you two think there’s something I could change about my approach or perspective!”
Most of my sexual experiences have been fairly vanilla. Of my two main long term partners, one would not consider any kink, and the other made me feel strange if I wanted to try anything different and didn’t let me know what she wanted to experience either. Now I kind of have a hang up regarding sex, in that I don’t feel comfortable pushing forward with something non-vanilla, even if it excites me. Also, I am completely uncomfortable if I am not the aggressor. How can I get over both these things?
A 38 year-old single woman with a kid writes, “Would it be possible to have you take a look at my OKCupid profile and hypothesize why I keep getting guys who are upfront from the beginning that they aren’t looking for a something long-term? They say they’re monogamish, busy, etc. I’m interested in, though not desperate for, a life partner. I also find many of the men who message me are far older than I am and/or from out of state. Neither of those things is particularly interesting to me.”
A 42 year-old straight male who cross-dresses, is only interested in women, and only wants an LTR writes, “I’m stuck with a paradox: I have discovered that if I am not perceived as forthright from the start (I don’t always dress up, just like women don’t always dress up), the revelation of what makes me different can be off-putting. On the other hand, if I put who I am out there from the start, no one picks me. OKCupid has in the past provided women who pick me and that has been extremely rewarding. How can I increase my ability to find women who would want, not merely accept what makes me different?”