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DateWell

Overthinking Ollie

“How can I be sure this is the right person for me?”
  • Persistent uncertainty regardless of how many dates
  • Relentless second-guessing and self-questioning
  • No evidence or reason is ever sufficient to settle an issue
  • Often looks to buy more time to avoid making decision
  • Would rather walk away over making a decision
  • Fear making the wrong choice more than missing a good relationship
  • Highly unlikely to trust their gut feeling

Emotion:

Mental exhaustion + Fear of regret or misjudgment

Inner Mood:

Constantly second-guessing, uncertain, and overanalyzing. There’s a sense of being on high alert, waiting for the other shoe to drop. There’s also a subtle feeling of frustration at not being able to trust one’s own instincts.

Disclaimer

We understand that in presenting these dating types, we risk causing offense. After all, we’re describing real people—people like you and me.

We want to be clear: we recognize this challenge, and we’ve worked hard to avoid hurting feelings. We’ve agonized over every word to be as sensitive as possible.

At the same time, we’ve prioritized being real and honest. Too many people are struggling way too hard for way too long, and our goal is to be straight-up about how internal patterns and mindsets can contribute to that.

We’re willing to be liked less if it means helping more. That’s why we didn’t always soften things if doing so would water down the message or reduce its usefulness.

That said, it’s entirely possible we got some things wrong. We’re open to hearing that, and we’re willing to apologize and revise. If you feel anything in the “So Me” types should be changed, please let us know.

We ask that you comment with the same level of respect and sensitivity you’d want for yourself. Together, we can help bring more happiness to Klal Yisrael.

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