How to Ask the Hard Questions in Dating

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Are you afraid to ask the hard questions in dating? My podcast guest, Dr. Duana Welch has scripts and tips for you.

Do you shy away from asking hard questions in dating? Do you share too much early on? My podcast guest, Dr. Duana Welch has scripts and tips for you. She is the original Love Factually author and coach known for using social science to help find and keep the right partner. She has taught at universities in Florida, California, and Texas across 20 years. Her Love Factually books are now out globally in five languages. Her client practice is global.

In this episode of Last First Date Radio:

  • The best time to ask hard questions in dating
  • How to talk about the hard stuff without it sounding like an interview
  • How to get clear about what you need and want early on
  • When and how to share about your life stories
  • Why people find it so difficult to bring up the hard stuff…and the consequences of waiting too long

When and How to Ask the Hard Questions in Dating

What are some of the hard questions in dating that people are afraid to ask?

Some hard questions are behavior-related and don’t even require a question. Observe signs of kindness and respectfulness, don’t ask about those qualities. Look at how they treat the waitstaff or talk about others.

If you want to know why someone’s marriage ended, a great question to ask is, “If your ex were here with us right now, what would they say was the reason for the breakup?” Then ask, “Can you tell me more about that?
A good follow up question is “Do you share your ex’s opinion about why you broke up?”
If they insult their ex’s integrity as a person, that’s a big red flag.

“How many children do you want?”is a good question to ask right away.
“Are you looking for a commitment someday?” is an important question, but don’t say, “Do you want to get married?”, because that sounds like a proposal.

“If you could have a relationship that matched your ideal, what would that look like?”
No matter what they say, you have to be willing to assess these qualities. All the information is valid.

Share a bit about what you want, then ask what they want.
When you reach a clear no with someone, don’t ghost them. Tell them, “That’s such a shame for me. I really enjoyed talking to you, but it’s just not something I can do.”

If they ‘life-dump’ (share their whole life story) right away, it’s a sign of a serious life imbalance.

Why do people wait too long to ask the hard questions?

Two main reasons:

  1. If you’re going to reject them, they’d rather you do it faster.
  2. People who don’t ask the hard questions are usually afraid of being alone.

When is the best time to talk about the hard stuff?

It’s like a dance. Ask yourself, do they need to know this about me yet?
STDs don’t need to be disclosed until you’re having sexual contact.
Intimacy is a growing reciprocity. Give a little first, then build to the core of the issues.

You don’t want to hold back important information, but don’t tell too much too soon, because people will reject you out of hand. If your story is “I’m unemployed”, think of a way to share that. You can say something like, “During the pandemic, a lot of people were laid off. I’m actively searching for a new job on LinkedIn, and it looks like they’re hiring again.” Put a positive spin on it.

People are asking these hard questions in dating to see whether we have resilience. Be gentle with yourself and others. And remember, you don’t have to answer any question that makes you uncomfortable.

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