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What is the right approach to engage with someone I am attracted to?

Engage with totality and honesty, for love is a fleeting wind that must be met with your full presence before it slips away. Choose wisely, and when you do, commit without hesitation.

— Osho
According to Osho, when you’re drawn to someone, stop calculating the “right dose”—enter totally, with gusto, while they’re present, because people and chances are fleeting. But first be honest about your own taste: if the flavor isn’t truly yours, involvement becomes torture. So choose with clarity, then commit without hesitation—meet the wind with totality before it passes (and before it devours you).

If they’re truly your taste, jump in fully now; if not, don’t start—and stop overthinking.

In His Own Words

From the Discourses

Passages where Osho speaks to this question — each links to the complete discourse.

Hammer On The Rock · Discourse 30
1976-01-14 · Chuang Tzu Auditorium · English
[Osho went on to ask the sannyasin how she was feeling on the whole. She replied: I think I like to move really close to people, but then I become afraid that I will be rejected. But I've been able to come closer to people than ever before.] No, you will be able to move even closer. You need first to see that when somebody rejects you, he is not in fact rejecting you; he is simply saying that he doesn't fit with you. He may even like you, but somehow the energies don't fit. So no rejection is personal -- nor is any acceptance personal; deep down they are energy phenomena. If somebody falls in love with you and accepts you deeply, it doesn't mean that he has accepted you, or you, him.
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The Path Of The Mystic · Discourse 13
1986-05-10 · Punta Del Este, Uruguay · English

Beloved Osho, when I meet with someone in the heart I become completely intoxicated by the experience. In those moments I feel gloriously fulfilled and ecstatic. A tremendous amount of energy starts moving in my body and I feel to go totally with it, to lose myself in it. Then -- and it always happens -- the pendulum makes the natural swing in the other direction and I find myself clinging to the recent moments of love and become unhappy. This feels like a very old pattern. I would be grateful if you would talk about awareness and love, or how to let go but not get lost?

What the woman is saying is perfectly true. If every lover had understood it, life would have been a very joyful experience. But lovers cling; they want to be together twenty-four hours a day. And they destroy something beautiful because they don't give a rest. It becomes a burden rather than a joy. They don't allow a gap for longing, for waiting. So all lovers who get married soon find that the only mistake they have committed is the marriage. All love marriages fail -- without exception. The only successful lovers are those who, by circumstances, by society, by parents, were not allowed to meet, to marry and to be with each other. They are the only successful lovers. They love each other to the last moment of their lives; their longing goes on growing. They are unhappy, they are miserable that they cannot meet the person they want to…
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God Is Not For Sale · Discourse 8
1976-10-19 · Chuang Tzu Auditorium · English
And it is just a question of courage. Certainly when you get into things, you get into troubles also. It is very easy to sit before the TV and see people loving each other; nothing is at stake. You can turn it off any moment But if you fall in love with a woman you cannot turn it off so easily. There will be anxiety and turmoil and conflict and struggle, but that is beautiful -- that is what life is! It will create many troubles but it will bring many pleasures also. There will be many ups and many downs. Those downs are worthwhile because they are what life is all about. Even if you can have a few moments of love with a woman and days of conflict and fighting and nagging, it is worth it; then too, it is worth it. One has to pay for everything.
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The Cypress In The Courtyard · Discourse 16
1976-06-19 · Chuang Tzu Auditorium · English
But there is a person for you. He will be tremendously happy meeting you. But before you can knock on the right door, you will have to knock on many wrong doors. If you are afraid of knocking, afraid that somebody may not open the door, then you will never be able to find the right door. So take courage. It is worth it. Taking all risks is worth it because that is the only way to grow. Knock on many doors. If the person there says, 'I am waiting for somebody else,' just thank him. Perfectly good. There's nothing wrong in it. Why do we take it as a personal offence? I go to somebody and I like the person, but the person does not like me. Why should I take it as a personal offence? There is no problem in it.
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From Death To Deathlessness · Discourse 30
1985-09-04 · Rajneeshmandir · English

Beloved Osho, last night after dancing with you, my feeling was that I have missed my whole life up to now in hesitation, and that I should do something. But what to do?

When death is so close, who feels hungry? Who feels thirsty? The question was to get as far away as he could reach by sunset -- the further the better. And by sunset he had ridden hundreds of miles away. As the sun was setting, he tied his horse to a tree in a garden outside some unknown city, and he patted his horse and said, "You are really great! You ran so fast -- I have never seen you running so fast. I am immensely grateful to you." Just at that moment the black shadow appeared behind him. The king looked back; the shadow laughed and said, "Your horse is really fast. I was worried whether he was going to reach the right place or not, but he managed! This is the tree, and this is the time. The sun is setting and I am immensely grateful, just as…
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