5 Questions to Ask on a First Date (with Chai Benson)

In this episode, Elizabeth sits down with therapist Chai Benson to talk about how to assess someone on a first date—before you get emotionally invested or waste your time. They break down the key questions to ask, how to spot red and green flags early, and why dating with intention is essential (especially for highly sensitive women). If you’ve ever found yourself caught up in chemistry without clarity, this episode will help you date with more discernment and confidence.

Show Notes

Why assessing a first date matters (and saves you time + energy)
How to decide who is even worth going on a date with
The importance of knowing what you want before dating
The 5 key questions to ask on a first date
How to tell if someone is truly seeing you
Work-life balance and what it reveals about relationship potential
Leadership vs. go-with-the-flow dynamics in dating
Why talking about past relationships is actually a good thing
How someone handles conflict (and why it matters early)
Red flags to watch for (incongruence, blame, dismissiveness)
Green flags to look for (self-awareness, curiosity, emotional presence)
How to avoid getting lost in fantasy and stay grounded in reality
What “true love” really means—and how to recognize it

Links for Chai Benson:

Private therapy practice website: LBCTherapy.Services

Marigold's website: MarigoldMM.org

IG: @marigoldm_m

💗 Want my free guide “5 Dating Mistakes Every Highly Sensitive Woman Should Avoid”? Access it HERE

💗 Got a dating or relationship question for me? Tell me a bit about your journey — I read every message. Reach out anytime at elizabeth@elizabethrave.com

💗 Ready to call in your true love? Book a free 1-hour discovery call HERE

💗 Follow me on social media

Facebook: https://www.facebook.com/ElizabethRaveCoaching/
Instagram: https://www.instagram.com/elizabethravelovecoach/
My artwork (Instagram): https://www.instagram.com/elizabethraveart

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