Two Sense: How Do I Get to the Third Date?


I'm a 35-year-old woman trying to compete in the brutal SF dating scene. I'm considered attractive and seem to find plenty of guys to date. I'm averaging one date per week, which I think is pretty good. I don’t expect every guy to be into me or vice-versa. Here’s the problem. Typically, we'll hit it off on the first date. I feel genuine warmth and enthusiasm, although as a rule I don't have sex that soon. But lining up the second—or, especially, the third—seems downright impossible. The guys generally answer texts and engage, but then shy away from meeting again even after insisting that they want to. Am I doing something wrong or is everyone else a flake?

He Said: Dating is a numbers game. It sounds like you are hitting your numbers but they have yet to produce the desired results. That means you'll get a lot of what you describe—flakey guys not quite ready to get serious. Let's face it, we’ve all been on the other side of the dinner table. You meet a cute, sweet or funny guy. You are charmed, even dazzled. But after you have slept on it, the glow dims. You begin to think more critically about the date, and you realize you were actually uncomfortable with some of his jokes or insights. Or that your wine goggles made him look a lot more attractive than he actually is. Or that age difference, which you dismissed upon meeting, now seems inappropriate. The only thing you are doing wrong is taking this personally. Every rejection is in fact bringing you one step closer to your goal. The right guy is just around the corner.

She Said: I’m always loath to blame a disappointing pattern on the environment, because even if the environment is part of the problem, it probably won’t change. So unless you’re ready to leave San Francisco, let’s take the option of “San Francisco guys are flakes” off the table. They may indeed be more flakey than guys in Omaha or Portland or New York, but so what. People meet long-term partners in San Francisco all the time. Let’s focus instead on what you can change. He Said is right in that dating is a numbers game and if you keep going, you’ll eventually succeed. But if you want to hasten the process, here are some things you might try to up your numbers for Dates Two, Three and beyond.

1. Be a little more selective in whom you actually meet. If you’re averaging one first date a week, I’m assuming you’re online. Screen those first dates more closely; only meet men who openly state that they’re looking for a relationship.

2. You say guys usually “respond to texts” after the first date. That sounds like you initiate the texts. Experiment with not doing that and see what happens. It may sound politically incorrect, but if you want a man to pursue, you must let him. He can’t pursue when you are doing it for him. Of course, if you’re more comfortable being the pursuer, by all means go for it. Sooner or later you’ll hit pay dirt.

3. When you do text, be brief. The more socializing you conduct by smart phone, the less chance of seeing the person anytime soon. This holds true for friends as well as dates. Though it’s terribly old-fashioned at this point, try to direct the communication and setup of subsequent dates to a phone call instead of a text. When he texts to inquire of your availability, write, “Call me (I know, so 2003!) to set something up.” If a man can’t dial your number, he can’t be a boyfriend.

4. Instead of focusing solely on one-on-one first dates, seek out group experiences where you can meet a number of like-minded men at once. One glance at the page for San Francisco shows countless group events for foodies, outdoors lovers, techies, film fanatics, oenophiles, you name it.

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