Seeking True Love

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

Episode Summary

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.

Episode Notes

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