How to Date in Five (not so easy) Lessons


I’m not sure why exactly it is easier to arm the student population than to simply reinforce the idea that sexuality is an extension of a relationship. I’m not advocating a return to a repressive sexuality. Rather, I’m thinking that the brilliant talented kids who constitute our country’s future might benefit from learning how to date.

I once suggested to a client that she have dinner with a man before having sex with him. She looked at me in horror.

What?” she exclaimed, “Have a meal with someone I’ve never met before? Are you crazy?”

No, I’m not crazy.

No matter how it may be publically depicted, the alcohol and drug fueled hook-up sexuality simply feels awful – especially the next morning when your breath stinks and you can’t find your underwear. Let’s get real. Sexuality without intimacy isn’t quite as fun as the hype would have you believe. Further, you get hurt or hurt someone else when you neither know nor understand your partner.

Finally, by popular demand, I am posting my five tips toward successful dating. In other words, here are some ideas for how to behave before you even think about having sex with someone. Here goes:

First, listen. You aren’t that important. When you are meeting someone for the first time try to find out more about who they are. If you both people practice the fine art of asking each other questions you might find yourself in a meaningful conversation. You actually might get to know someone else who might even be interesting enough to enlarge your personal world ever so slightly.

Second, try doing things together instead of sitting around a table behind a drink. When you present your best-self act with polished defenses you and your fellow mannequin will have extinguished any chance of spark. Instead, take a walk through the park. Ride bikes. Watch a great show. Volunteer together. Tour a museum. Shared activities make it easier for your more authentic self to spontaneously emerge. That’s when sparks happen.

Third, be honest about what you want. If you really want to be a friend with benefits no tears allowed when your special someone declares their love for another. It’s okay to only want a casual sexual relationship but no complaints when that’s all your partner gives you. But if what you really want is something with potential don’t settle for anything less. Better to wait than to lie about what you really want. Better to be disappointed up front than later.

Fourth, try doing things with groups of friends. This reduces “dating” pressure. You can observe each other gracefully and get to know each other in a variety of contexts. You can see how someone you like interacts with others, and observe them acting more naturally.

Finally, no one is perfect, especially you. Remain mindful of your shortcomings. When you meet someone else who has some, you’ll feel right at home. This doesn’t suggest “settling.” It means accepting that the deepest and truest love happens to real essentially imperfect people.

Being a real person has gone out of favor, along with the extraordinary beauty of sexuality. Old-fashioned romances have become downright counter-cultural. So if you decide to give it a try, keep the secret. You might find yourself pleasantly surprised at how exciting intimacy can be.

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