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?”
Our first message from this fellow was a sarcastic, “What would your advice be for me, being 40, bald, a minority, and despite being ‘a great guy,’ having trouble finding someone I genuinely connect with?” Were we talking to Montel Williams? The angry ghost of Gandhi? He then wrote back a story of a date that led to the dreaded “let’s be friends.” Now he feels a connection and isn’t sure whether he should stick with the great, albeit new, friendship or push for something more.