Choose to Date Differently: How to Strategically Approach Dating

The solution to dating in San Francisco boils down to one simple concept. Choice.

You heard me.

Dating in San Francisco is about choice.

Earlier today, my head was spinning as I tried to figure out the dating problem in San Francisco. First I Googled “why is dating in San Francisco…” and Google finished my sentence for me with the simple words “so hard.” ​​

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After reading a few articles, I had the idea to make a flow chart of my life to figure out what parts of dating have been easy and what parts have been hard. I realized I didn’t know where to start. My life is too complex, too full of choices. And, I realized, so is dating in San Francisco.

So, when faced with an overwhelming and complex task like making a flow chart or, I dunno, dating in a city like San Francisco, where does one even begin?

1. First, focus. Clear your workspace. Set aside distractions. Create a space that is conducive to the outcome you want to create. In dating, this might look like discontinuing phone calls to your ex, or that guy you kinda have a “thing” with but who never really seems to show up when you need him to (and always seems to show up when you don’t really want him to.) It could look like, cutting back on work, if your life is too cluttered by work.
2. Second, prepare. Visualize and talk about what you want. Sharpen that vision, develop clarity. I’m NOT talking about writing a list of things you want in a partner (handsome, tall blonde, funny, good job, cute dimple, etc.) I’m talking about what YOU want for yourself – a committed relationship? Casual sex? A slew of dates every week? As you visualize and get clear about what you want, take that fantasy monologue out of your head and bring it in to either writing or dialogue to further develop your vision. Talk to a friend, coach, therapist, or just write it down in a journal or a piece of paper.
3. Develop an ability to talk about what you want naturally, in natural settings. You’re practicing talking about what you want, which is what we do in relationships. As a bonus assignment, learn to also engage others on this topic, and develop an ability to listen to others talk about what they want. Practice this skill on dates. Really listen to the other person, and you will get to know a lot about who they are, what they want, and if they are a good partner for you given what YOU want.
4. Fourth, experiment. Cultivate an attitude of openness, experimentation, and learning. Now, go out and experiment. Try approaching that guy or girl you like. See how it goes. If it worked, great. If it didn’t, what can you learn about who you approach, how you approach them, or about things like persistence and tenacity?
5. Fifth, be discerning. Go back to steps one and two. When you’re talking to someone you like, think about what you want and what you visualize. Is this person someone who can be what you’re looking for? If yes, move to step 3, and find out what this person is looking for. Are they looking for casual sex while you’re looking for a committed relationship? If yes, that’s awesome. Thumbs up to them and thumbs up to you for noticing now. Move on.
6. Be persistent. Have you ever looked for a job (for example, a job in San Francisco that is not in tech)? You know what I’m talking about. What do you do to get a job? Pursue all leads, look in every corner and direction, apply every day to jobs, and follow up.  This translates in dating as: don’t be a flake.  If you are only showing up when you feel like it, you will see reflected back to you a lot of singles who only show up when they feel like it. If you show up fully, you will begin to sort out the flakes from the non-flakes.
7. Most importantly, acknowledge your fears but don’t be guided by them. Be honest with yourself. You’re afraid of something. Congratulations – you’re a vulnerable and awesome human being. We all are scared of something when it comes to relationships. Don’t ignore your fear or it will lead you and you will somehow give yourself away and look like one of those obviously insecure people. Instead, acknowledge your fear, and from there, make a clear choice about how willing you are to face it. Let’s say you’re afraid of rejection. You’re at a bar, you see a guy/girl you’re into. Acknowledge your fear and ask yourself what you really want (see steps 2-4). Give yourself a peptalk. Say “I know you’re scared, but I know you can do this differently and get what you really want out of this situation.” If nothing else, you will at least get the confidence in yourself that you can go up to someone you really like and that you can face your fears.   Let’s say the situation is commitment. You notice that whenever a relationship gets to a certain point, you call it quits or get bored. Next time it happens, notice that it’s happening. Say to yourself “I know you’re scared. How can I do this differently?” Make room for something different to happen. Make that choice for yourself.