LILY Letter 16: Risks Worth Taking

July 27, 2021

You cannot find love without risk. This is a fundamental law of nature. Ultimately, the games we play in dating are all attempts to violate this law. You might ask your friend to talk to the person and see if they can tease out a revelation about that person’s feelings for you, without telling the other person how you feel. You might have a party and invite twelve people, including the one you are actually interested in. You might strategically plan to “accidentally” run in to the person in the hope that a conversation will result. You might post something on Facebook that you think is calculated to impress the other person, hoping they will notice it. All of these “games” (and a limitless number of others) are attempts to find love without risk—or to get the other person to “go first” in showing interest.

To date someone you are attracted to requires one of you to risk rejection and make an overture to the other. The other must then agree to take the next step. The greater risk is by the one who “goes first.” Asking someone for a date is saying, in effect, “I like you and I want to get to know you better.” Being turned down feels to some like the other is implying, “Well I’m sorry, but I don’t feel that way about you.” That is a very deflating thought. For some, it even provokes them to question their own worth because someone else could not see it clearly. There is no dating strategy we can teach you that will avoid the need to take a risk and put your heart on the line. The best strategy is to become more comfortable in your own skin and develop some courage—which means to overcome your fear and take action in spite of it.

It also requires risk to be authentic in dating, rather than wearing a mask and trying too hard to impress your partner. If I choose to pretend to be something I am not, the other person may fall in love with the mask I am wearing and not my true self—and, deep down, I know it and cannot truly feel loved. On the other hand, if I am vulnerable and allow the other person to “see” my flawed self and my insecurities, that person’s acceptance is real, and I can trust it. That is the sweetest feeling in the world. In a way, it is like Jesus explained to the woman at Jacob’s well, stating “Whosoever drinketh of this water shall thirst again: But whosoever drinketh of the water that I shall give him shall never thirst; but the water that I shall give him shall be in him a well of water springing up into everlasting life.” (John 4:13-14.) If I drink the water of imitation love, the relief I feel will be temporary. But if I drink the water of real love, the effect will be lasting because I know the other person accepts me, knowing my darkest secrets and deepest insecurities. Bravely asking for what you want and being yourself in dating efforts is a risk worth taking. On the other side of fear is life’s sweetest reward.

LILY Pod Episode 23: Relationships and Risk in the Mid-Single World

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