Asking Over Assuming: Yes, You Can Ask Hard Questions In Online Dating Conversations

Hi, I’m Amanda. Welcome to my blog, where I share online dating advice, tips, tricks, and strategies, all based on my professional training and personal experience.

Grab my free Online Dating Red Flags Checklist, so that you know what to look for in matches, conversations, and dates.

I was a horrible communicator when I was younger. It’s funny to say that, having now been a therapist for over ten years and being on the more direct end of the spectrum. But back in the day, it felt nearly impossible for me to communicate my feelings and needs, particularly in romantic relationships. I found myself constantly guessing what was going on for the other person, what they were thinking and feeling, rather than just asking.

I remember one situation in particular in which it took me almost a month to build up the courage to ask someone I was seeing a fairly basic question about our status. When I finally did, it wasn’t the answer that I was hoping for, but even then, the anticipation felt so much worse than actually doing it.

It felt incredibly scary and overwhelming to express my feelings and needs and to ask basic questions. I worried that I would say the “wrong” thing. That the other person would think that I was overly emotional or sensitive. That I was being “that” woman. That by saying something, I ran the risk of pushing the person away.

I couldn’t see at the time that by holding back, I was inadvertently moving closer to the things that I was fearing, all while becoming a smaller version of myself in the process.

I hear the same fears from women about dating. When I suggest that they ask the person the question that they’ve been wondering about in their minds, the immediate reaction is fear and a response of, “Oh I can’t do that.” It feels scary, overwhelming, daunting, and just plain wrong.

Somewhere along the way, we as women were taught that basic, healthy communication isn’t okay. We were taught that it’s not okay to ask questions.

There are numerous consequences to this, the first being that we make ourselves smaller versions of ourselves. When the person we’re talking to says, “I’m in between jobs,” and we have a negative reaction to this, our internal dialogue might look something like this:

“I can’t ask what he means by that. It’s probably a sensitive topic, and I don’t want to make him feel any worse than he probably already does. If he says he’s in between jobs, that probably means he’s looking for other positions. I should be grateful for my privilege of having a job and an income.”

In all of that rationalization, we’ve inadvertently shut down the fact that this person’s comment made us feel uneasy, particularly if we wanted an equal teammate and partner in not just finances, but life in general. Nowhere in that internal dialogue is our feelings and needs. It’s all about the other person’s feelings and needs.

Also, notice the frequent use of the word “probably” in that internal dialogue. When we don’t ask the hard questions, we don’t actually get to know the person. In this case, you have no idea whether the person has serious struggles that prevent them from holding a steady job, or if they fell on some bad luck that they’ll quickly recover from. Instead, you’re left wading in a pool of uncertainty, really not knowing the person at all on the other end of the conversation.

Even worse, we can make assumptions that aren’t actually true, leading us to think that we know the person when we really don’t. Imagine assuming that this person has just run into some rough times, when in reality, they’ve been fired time and time again for stealing money from the companies that they work for. This assumption means that you think that you’re dating one type of person when you’re really dating someone entirely different.

Finally, not asking questions wastes your time. When you don’t get to know the person early on, you drag this process out much longer than it needs to be, meaning that what you could have learned in a few online conversations instead takes four months of dating to figure out. Four months in which you could have been investing your time in people who would actually be a good fit for you. Sadly, I’ve seen this process drag out even longer for people, sometimes to the point of several years. It might feel impossible, but it’s what happens when the tough questions are sidestepped or avoided.

Asking the hard questions is scary, AND there are so many benefits when you’re willing to take that step.

First, it keeps you tuned into your own feelings and needs. This isn’t selfish or mean. You’re not looking for a person to go to lunch with; you’re looking for the person to spend the rest of your life with. This isn’t something to take lightly. What you want and need in a life-long relationship is important. When you give yourself permission to say, “I’m sorry, what happened with your job?”, you’re not only being kind to the other person, you’re making your feelings and needs a priority.

Asking these questions also helps you to truly get to know someone. If the person says, “The tech company I work for just did a massive layoff. It’s been difficult, but I’ve already got a few interviews lined up,” that gives you a lot of information about the person that you need in order to assess fit. You’re probably going to feel better proceeding forward in hearing that person’s response. If the person says, “It’s just been hard to find work lately,” then that gives you data that the person isn’t exactly forthcoming. All of it is important, whether it ends up being what you want to hear or not.

This saves you SO much time and energy. By cutting to the chase in a kind and curious way, you just made your decision much easier as to whether to continue in the connection. Every question you ask someone is like being at a yellow traffic light, with the other person’s response giving you information as to whether that light just turned red or green. Without asking questions, you’re stalled at the yellow light for a very long time.

If the thought of asking someone these open questions still feels scary because you’re worried about pushing the other person away, remember that these are healthy tests in a connection. If you ask someone what happened with their job, and their response is to say, “I can’t believe you would ask me that; that’s so insensitive,” YOU DID NOTHING WRONG. Their response gives you data about THEM, not YOU. It sucks to be on the receiving end of comments and behaviors like that, but you can also take comfort in knowing that by asking the question, you dodged a bullet early rather than later.

Remember too that it’s not about whether you ask; it’s about how you ask. Saying, “Please don’t tell me you’re a person who can’t hold a job,” is not the same as saying, “I’m sorry that you’re in between jobs; would you mind sharing what happened?”

We as women are often taught that being assertive = being mean, but it’s not. Assertive means expressing your feelings and needs. You can do this in a way that is tactful and kind, or you can do it in a way that’s attacking and mean. Obviously we’re aiming for the former.

Asking questions in a tactful and assertive way is okay. It’s not only okay, it’s necessary to form strong, healthy connections, as well as to feel empowered and stay authentic to yourself in the dating process.

*Don’t forget to grab my free Red Flags Checklist! You’ll learn everything you need to know to scan for red flags in your swiping, conversations, and dates.