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 divorced straight woman in her early 40s wrote, “I love my ex husband, and I’m so sad that we didn’t work out. I would get back together with him now, but he says he’s done. I’m still confused as to why that didn’t work out. We both love each other so much. I have been dating a lot for two years now, and I have yet to find a guy that I really connect with. I wonder if I’m doomed to be single my whole life now that I’ve lost my ex husband. Do you have any advice to give me other than ‘soldier on and I’ll eventually meet someone’?” We do, of course, have some advice, and the writer included a link to her OKCupid profile, which figures into our response.
“I’m currently fooling around and flirting with a few guys. I’m newly single and having a lot of fun. I sometimes wonder if monogamous relationships are just not for me. I tried it and I get bored really easily. I like getting a lot of attention and I get frustrated with just one guy. I feel like there’s no way one guy can give me all the attention I crave. Is this just a phase because I’m young and selfish or is this just me?”
A woman in her early twenties from the New York suburbs wrote in the heat of the moment that, “I was about to text this guy that I have been having casual sex with for the last three months, several times a week, and tell him I need to stop. We met online. He is 10 years older than I am, and I think I may be developing feelings for him, although I try and act cold and detached. I have a lot of other specifics, but I don’t want to bombard you. It was just super weird that I came across you just now.”
“I was in a FWB situation for almost 8 months with this guy. We never went on real dates and mostly met at his drum studio or apartment, talked, and had sex. For me anyway, it was a rare intellectual connection combined with great chemistry. Sex was great, conversations were great, and time passed so quickly with hi. He was not OK with the polyamorous thing and didn’t want to get emotionally involved but was OK with having sex since it was out in the open. I was OK with simply enjoying the times we had together. So, that was working well until one day he just dropped out in the middle of rescheduling one of our meetups because the schedule that day didn’t work out. Like all of a sudden, gone. To this day I’m just still extremely puzzled by this. I’ve moved on and I’m not mad or anything, but just deeply curious. Like, what the hell happened?”
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 47 year-old straight guy in a rural area is new to dating because he’s shy. “The one relationship I had after high school was because she was the aggressor. That was back in ’87, and it lasted about a year and half. I fear putting sexual information in my dating profile. Like, I fear I may be sitting in front of a potential employer or even my current employer or fellow employees and they start laughing and say ‘So, I see you like to have your women’s genitals clean shaven?’ or ‘So, you love to give head to women?'”
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?”