I Just Ask a Lot of Questions; I'm Not Trying to Interrogate Anyone!

By Dr. Robert Wallace

March 6, 2026 5 min read

DR. WALLACE: I sometimes think I ask too many questions when I'm at the beginning of starting to date someone! A lot of the questions I bring up are mild and easy to answer, and those tend to go pretty well with most people. However, I often think of interesting questions to ask as a conversation moves along, and more than once, I've noticed that the replies I get are either stammering, long pauses or deep breaths with a long exhale before some kind of mumbled answer that doesn't really suffice tumbles out in response to what I specifically asked. And from there, of course things get awkward!

Is it better to ask many questions early on in a potential romantic relationship, or to stay silent and simply observe how someone reacts gradually over a period of time? — Not All Questions Get Answered, via email

NOT ALL QUESTIONS GET ANSWERED: Your letter did not specify exactly what types of questions you're asking that bring about these stumbling or silent responses, but that aside, you're absolutely learning new information all the same.

There really is no right answer as to how to proceed in the early stages of meeting someone new. It's more of a personal choice and personality style that guides most people. You are naturally outgoing and inquisitive, therefore you're quick to drop a question in front of someone new.

My advice is to remain true to yourself, but do take some time to think about what specific questions you've asked in the past that have brought these difficult or even nonverbal replies. If these are questions that are not all that important to you or to the situation you're in, do your best to avoid some of those in the future. However, if the questions you're asking are indeed relevant to the personality, actions or past experiences of an individual you'd like to get to know better, I feel those types of questions are absolutely fair game. And consider this: The earlier you learn something about someone, the less time you need to invest waiting to inevitably find the same information out much later, perhaps in a more difficult and less advantageous light.

WE'RE STUCK TRYING TO START OUR "DORM-BASED" BUSINESS

DR. WALLACE: My best friend and I are 19-year-old college students, and we have a great idea for what we call a "dorm-based" business.

However, despite our great idea, we find ourselves limited with the capital and manpower needed to carry our plan out, even though the two of us definitely have some free time to work on the business.

What's the best way to potentially overcome not having enough manpower to truly get a new business idea at least moderately off the ground? — Our Great Idea Is Presently Stalled, via email

OUR GREAT IDEA IS PRESENTLY STALLED: First, congratulations on having what you feel to be a great idea, coupled with the time that you and your friend can allocate and dedicate toward developing your game plan.

You identified two specific areas that are definitely a challenge for you at this point: the lack of capital and a need for more manpower. Regarding the manpower issue, not knowing the nature of your business, but assuming that it is for lower-level work that needs to be done, perhaps you're thinking about hiring an individual or two, or a small group of individuals to help move your idea forward.

If that's the case, your manpower situation can be solved by having more capital. You may have to start slowly and build up your manpower needs as you're able to afford them, but this is indeed something you may be able to achieve.

Moving to the topic of capital, you could solicit outside capital from family members, friends or trusted people within your circle of acquaintances in exchange for a slice of equity and/or profits. You may also be able to achieve a small loan from someone close to you that you could pay back gradually as you get things off the ground.

Another strategy might be for you and your friend to keep developing your business idea while you spend some of your available hours now working at jobs that will pay you the most for the hours you can work. Working at an upscale restaurant as a server or finding other potential part-time jobs in your community may allow you to raise some capital that you can gradually pour into your business.

Dr. Robert Wallace welcomes questions from readers. Although he is unable to reply to all of them individually, he will answer as many as possible in this column. Email him at rwallace@thegreatestgift.com. To find out more about Dr. Robert Wallace and read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate website at www.creators.com.

Photo credit: Towfiqu barbhuiya at Unsplash

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