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?”
Have I ever seen people successfully do this? No, I haven’t. Then again, people don’t write to us when they’re successful. However, I know that your real question is whether I would recommend that you try this negotiating tactic yourself.
In that case, my answer is “Almost certainly not, and then not as you describe it and it very much depends upon the presentation.” Here are three ways I see it playing out.
1) Blunt negotiation. “So, I’ve got these dates coming up … What are you going to do about it?” Something like this would mean that you were trying to turn your friendship into a hostage situation: “Move it to the dating zone, buddy, or I’m going to date someone else.”
There are so many ways that this is likely to backfire. If he’s not a pushover, he will see this as aggressive and offensive and think, “If she’s going to try to bully me into dating her, imagine what she’d do if we were actually a couple and had real conflicts? Now I’m not even sure that I want a friend like that.” It depends on the specifics of your relationship with this guy, of course, but I think many would respond like that–or at least with a good deal of caution. Also, if he’s really not interested and you’re too blunt about it, you’re really going to feel like a fool when he shrugs his shoulders at your threat.
2) Be subtle and see what happens. Perhaps, just maybe, on the off chance, if you make a point of casually referring to your upcoming dates while giving him signs that you’re interested, he could realize how amazing you are and that he might lose you if he doesn’t act now. And if he doesn’t respond that way, then you’ve both saved yourself some embarrassment. This is a pretty passive tactic, however–straight out of the romantic comedy playbook–and is most leave you feeling dissatisfied. You also risk ending up right where you started: not knowing if he’s actually into you or not.
2) Use your upcoming dates as a reason to be honest. I’m a fan of being straightforward, and to be clear, your upcoming dates are almost a non sequitor in this scenario. That said, you could introduce the topic of romance by saying that you have all these upcoming OKCupid dates, which is exciting or drudgery. Tell him you’re most interested in him and would love to use him as an excuse to not even go down the internet dating path, but you also value him as a friend and would continue to do so and pursue romance elsewhere if he didn’t feel the same way. Then you’ll have expressed your feelings and know how he feels.
This does sound like a terrible idea at first blush, and upon reconsideration, I still think it’s terrible. If you care about someone and have feelings for them, the only reasonable thing to do is be honest. You don’t really want to continue a friendship in which the two of you have inequitable feelings, so what do you have to lose by putting your feelings for your friend out there?
Here are your real options: You can be a pussy who doesn’t take the risk of revealing her feelings, thereby continuing to be miserable and feel unseen by her friend, or you can be honest and go after what you want. The only way that anyone ends up in a lasting, caring, loving relationship is by taking a risk, being honest, and going after the person they wait
Another way of looking at this is by realizing that your other OKCupid dates are pretty much beside the point here–they have nothing to do with how you feel about this guy or how he feels about you. Moreover, he probably won’t get it if you try the negotiating tactic. Most people don’t think that subtly, and laying out your upcoming dates is most likely to lead him to believe that you’re not interested in him and are seeking other options.
We don’t know the full situation, but there are some possibilities as to why he hasn’t made a move yet. It could be that he has not thought about you in a romantic way yet. It could be that he doesn’t know that you’re interested, even if he is. It could be that he’s being a wimp. It could be that he’s not interested. The only way that you’re going to find out is if you talk to him and tell him what you want.
If the negotiating tactic were going to do anything, you’d get the same result much more reliably just by asking him out.
This is a terrible idea. It’s passive aggressive dating, and you need to be active and go for it. If you’re too nervous, get a little drunk or stoned together, try to kiss him, and see what happens. When both of your inhibitions are slightly lowered, maybe the truth will slip out. If it’s not the truth you wanted to hear, you can save a little face and blame it on the vodka.