I Hate Small Talk, So I Ask the Personal Questions Up Front. But Is It Ruining My Dating Prospects?

Self-regulating in 3…2…1

pacing-of-relationships: Two young women talking at dinner party. The one on the left is brunette and wears a black tank top. She is whispering something to the woman on the right. The woman on the right is blonde. She wears a black tank top as well.
Uwe Krejci/Getty Images

I hate small talk. Simple as that. I don’t want to talk about the weather. Cue the eyerolls. Instead, I wanna know what experiences made you who you are today. What irks you the most about other people? What are your deepest fears? What qualities allow you to trust a person? What place would you visit if you could be transported there instantly? Easy, right...? *smirks* People close to me often say that I ask a lot of questions, and to that I say, I’m not a casual person. I want to know the deep things quickly.

But how fast is too fast when meeting new people (especially potential dating prospects)? Are there designated check points at which it’s appropriate for me to know your love languages, your relationship with your parents or where that little scar came from? I spoke with a psychologist to learn more about pacing in romantic relationships and how to check in with yourself and others when engaging in more intimate conversations.

Meet the Expert

Dr. Naomi Ben-Ami, PsyD is a doctor of clinical psychology who received both her masters and doctoral degrees at Ferkauf Graduate School of Psychology at Yeshiva University. She serves as the clinical director at Williamsburg Therapy Group. She has previously worked as a staff psychologist at Mount Sinai Roosevelt Hospital’s Center for Intensive Treatment of Personality Disorders and has also held various positions at New York-based college counseling centers and community mental health clinics. Some of her specialties include relationship problems and communication difficulties.

Is There Such Thing as “Too Curious” in Early Conversations?

Sometimes. Depending on how someone shows up to a conversation, a person’s inquiry about something more intimate or private can be off-putting. Knowing how to read into a person’s body language, emotions and other indicators of discomfort can do wonders when it comes to steering a conversation. This is much harder to do digitally, so learning to pick up on written clues is important too. For example, the pace at which someone responds to a text, whether they take a significant amount of time getting back to you or respond right away, etc.

At the same time, many people will also be very flattered that you’re interested in getting to know them on a deeper level and will be happy to share more with you. This curiosity can validate your interest in a person and make them feel more at ease with you.

“Peoples’ reactions to personal questions from a new person can vary drastically. When done effectively, it can feel good for someone to be curious about us and it can breed a sense of closeness. However, if a line has been crossed, the questions might seem rude, intrusive, and elicit defensiveness or anger. Even if you believe it is appropriate to ask personal questions, it is best to start slowly and then gauge the response. It can also be helpful to ask yourself, “is this something I would be comfortable answering?” Dr. Ben-Ami says.

Eagerness to get to know someone and the thrill of learning about them can bring about the same kinds of feelings and emotions as having a crush, like excitement, pleasure, and enthusiasm. Being able to self-regulate may just be the key to “playing it cool” while you slowly, but surely figure out the other person’s communication style.

At What Point Can I Ask Deeply Personal Questions?

Like most things in life, the answer to this question is subjective. As unique as our personalities and preferences are, there is no one way to gauge a person’s ideal pace when it comes to diving right into the deep stuff. That said, there are ways in which Dr. Ben-Ami suggests navigating the pacing of your connection that may lead to more promising results, especially if you’re the curious type (like me!).

One of the most important parts of reading a situation according to Dr. Ben-Ami is to keep an eye out for the other person’s verbal and non-verbal social cues, body language and reactions to your questions. Starting slowly and keeping track of their replies will also help to maintain your pacing. You can also check in with them before asking a deeply personal question. For example, you might say, “Do you mind if I ask you about (insert potentially touchy subject)?” If you think something you’ve asked feels like it might have gone “too far,” check in with the other person to begin learning what they might be most comfortable answering and adjust your questions accordingly. Each interaction will be person- and context-dependent, Dr. Ben-Ami explains.

Keeping up with how a person responds to personal inquiries is the first step in determining how strong you’re coming on. If the person seems excited and willing and able to answer the questions you pose, by all means, ask away! If they seem more reserved, avoidant to answer or surprised by the inquiries, that may be your signal to pull back and stick to the surface. You can always dive deeper when the time is right.

What Are Signs That Question Might Go Too Far?

When entering into a new relationship of any kind, people come with their own baggage, meaning that person’s individual history plays a huge role into how they’ll react to intimate questions and whether or not they find these questions appropriate in correlation to the person asking and how early on they ask the question.

Dr. Ben-Ami says, “The point of appropriateness to ask a personal question is a very subjective judgment call. There is always an intricate interplay of many variables, like emotions, personalities, and the subjective experience of the people involved. Also, each person comes to a particular situation with their own interpersonal style and threshold for vulnerability and closeness. So this point will come at different times for different relationships. In some interactions, it may not come at all.”

All that said, some individuals might be willing to chat about, say, complicated relationships with their family members or more intimate details about their sex lives, while for other people, that may be crossing a line.

“Part of pacing and gauging appropriateness involves being in touch with yourself. Self-awareness and self-regulation allows for greater mindfulness of yourself and others. When regulated, you’re most able to see an interaction clearly, rather than be driven by impulse or clouded by anxiety,” Dr. Ben-Ami adds.

Signs Your Date's Uncomfortable with Your Questions:

  • they’re hesitant to answer
  • they seem quieter than earlier in the conversation
  • they switch the subject suddenly
  • they avoid answering the question directly
  • they redirect the question back to you
  • they avoid eye contact
  • they physically pull back from you

My Overall Findings

Overall, it’s important to connect with someone who meets your excitement and willingness to divulge. If you’re closer to being on the same page, those kinds of conversations will flow more easily and be better received by the other party. If someone’s inquisitive nature and curiosity comes as a surprise or shock to you, it’s good to notice that about your communication style. It may be something to look for and/or avoid in potential friendships or romantic relationships.

As for me, do I want to know everything about you? Yes. But will I be heeding Dr. Ben-Ami’s advice and slowing down just a bit? Also yes. They do say good things come to those who self-regulate. ;)

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Assistant Editor, Trinket Collector, Artisanal Latte Enthusiast

Delia Curtis (they/them) is a New York City based writer and Assistant Editor at PureWow. They have eight years of print and digital media experience covering lifestyle, fashion...