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Keeping it 100

Posted on January 12, 2020February 28, 2020 by Dating Goddess

The phrase “keeping it 100” comes from “keeping it 100% real,” meaning being 100% honest. It’s shorthand for no BS, don’t tell me what you think I want to hear, tell me the unvarnished truth. Don’t hold back.

I decided to try this with a man while we were exploring going from pals to more. His life is complicated right now, uncoupling from a long-term relationship. I wanted to understand his emotional state, goals and desires. I needed to determine if it made sense to become closer during this challenging time, or whether it would be best for all if we stayed pals and revisited becoming romantic after he was fully unencumbered.

I said, “Let’s play ‘Keeping It 100’. We can ask anything we want and the other person has to answer as honestly and fully as they can. No holding back because we think the other person may not like what we say.”

We took turns asking each other questions, and also answering the same question when appropriate. If I said, “Describe how you envision your life in five years” I would answer the same question after he answered.

This exercise was an amazing experience. We answered honestly. We were vulnerable. We admitted if we were uncertain about our answer. In the end, we were even more connected. It allowed us together to look at what would work for both of us at this time. We came up with some parameters and we made some agreements about what would happen next.

Having now gone out with over 120 men, I found this exercise to be refreshing. I tend to pepper my dates with questions, in part because I find so few men ask me anything interesting, beyond the “How long have you been single,” and “What happened to your marriage.” It always surprises me that after a date has answered one of my questions, he doesn’t say, “And how would you answer that?”

With keeping it 100, you can answer your own question. It gets the other person to really think about a question they want to know about you, without fear that it will seem too intrusive. Of course, one can always say, “I’m not comfortable discussing that at this time” if it does seem to go beyond your comfort level. In my experience with my new guy, we didn’t ask each other anything that seemed too personal.

It may be too scary for some, especially on a first date, or where you just want to have fun and don’t really care about getting emotionally attached. I don’t really want to spend time with a man who I don’t understand, so keeping it 100 helps me know him sooner rather than later.

Try doing keeping it 100 with the man you’re seeing, or the next one you date and see what happens.

Category: Dating after 40

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About the Dating Goddess

After her 20-year marriage dissolved, the Dating Goddess dated 91 men in 3.5 years. She shares her lessons, stories and advice for midlife women reentering the dating scene.

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