Skip to content

Dating coach’s top 15 questions you ‘must’ ask your significant other ‘disturbs’ fans

TikTok content creator and dating podcaster/author Jeff Guenther (therapyjeff on the platform) has offered his followers 15 questions they could ask a partner in order to get to know them better.

But the reactions hes received are a mixed bag, with some going as far as to say the answers to some of his questions would keep them awake at night. But he says this will help you get to know your partner more deeply and in turn could aid your relationship.

Rear view of Asia couple walking and talking together on a village street after returning from shopping.
Credit: Nitat Termmee

Therapy Jeffs 15 questions and prompts to get to know a partner better

In his video, Jeff Guenther offers 15 questions and prompts to ask a partner to get to know them better. 

He doesnt specify when during the course of a relationship he recommends asking them. Nor  thankfully� do any of them contain any modern dating jargon to make them hard to decipher. But they seem to make the most sense as topics of discussion for people who have decided to date with some commitment, and who have reached a certain level of intimacy.�

They are:

  1. Who was your first love?
  2. Tell me about the first time you experienced heartbreak, and the first time you ever broke someones heart.
  3. Do you believe we were destined to meet?
  4. Whats a relationship belief you once held strongly but have since let go of or evolved over the years?
  5. What problematic or unhealthy relationship pattern do you keep experiencing, and do you think it has come up in our relationship?
  6. How did you contribute to the demise of your last longterm relationship?
  7. Whats your biggest relationship regret?
  8. Was there a way I could have flirted with or approached you when we first met that couldve completely turned you off and prevented us from being together?
  9. What do you think is the absolute best thing about being in a relationship with you and do you think I appreciate it?
  10. Whats the most annoying thing about being in a relationship with you and do you think Im tolerating it OK?
  11. Whats a spicy fantasy that turns you on but that you would never want to do in real life?
  12. Is there a specific way youd want me to break up with you if I wanted to end things?
  13. Lets say we grow old together. Do you want to die first or second?
  14. Whats the wildest or weirdest place youd like us to hook up in?
  15. Whats your best relationship advice?

He then goes on to plug his new book.

Not everyone agrees Jeffs questions will lead to productive conversations

Some of the comments Guenther has received on his TikTok upload suggest a degree of division among his audience regarding whether these are worthy questions. Others are positive.�

No thank you, writes one TikTok user. The answers to some of those will keep me awake at night.

No way, writes another. Im way too sensitive for these questions!

A third praises the questions themselves, and presumably those willing and able to ask and answer them. But IDK if I want to know the answers.

A fourth says straight up that they dont want to know the answers to these. Other comments include the simple  horrifying  and advice not to ask number 12 to anyone with issues around abandonment, since it might trigger a negative response.

Who is Therapy Jeff?

Jeff Guenther is a licensed professional counselor  thats why he has LPC after his name on his videos. 

Online, he goes by Therapy Jeff. His website states that he completed a masters degree in family therapy at the University of Southern California, and a bachelors in child and family development at San Diego State University.

He lives in Portland, Oregon and runs a private practice.

His book, Big Dating Energy, is available for preorder from several major online bookstores and retailers. Besides making content for TikTok, he also produces longer form videos for the website Passes, a platform that allows fans to buy access to exclusive content and experiences from digital creators.