First Date Conversations – Addressing Taboo Topics with Tact

Let’s talk about stuff we’re not supposed to, today! As times have changed, so have the approaches we take with what we choose to discuss with our friends, colleagues, families and prospective partners. Topics to avoid on a date aren’t always the most obvious, and some questions may feel as though they need answering earlier than later, as you consider building a relationship with someone. In today’s world, there really are no objectively taboo topics on a first date; your discussions belong to you, and depend on who you are and your communication style. To boot, spicy questions on a first date might make things interesting. With this in mind, we’re still prepared to offer some best practices which we think might keep your new spark from abruptly fizzling out. 

Topics to Avoid

What you’d consider to be untenably large red flags which might interfere with fundamental compatibility with your match–whether philosophical, political, spiritual, or even just in terms of general lifestyle, likely don’t belong addressed on your first date, and not simply because they’re “topics to avoid.”

Why, then? Because they can easily be addressed beforehand.

If you’re working with a Tawkify matchmaker, your values are at the very forefront, and a lot of critical compatibility-defining information, with your consent, gets folded into our screening process, allowing you to bypass these so-called taboo topics on a first date. If you’re going this on your own and swiping your way toward love, though, discussions with your match before meeting should allow you a space to tactfully uncover any hard dealbreakers. To get here, you’ll need to know what those are for you.

Know Your Deal Breakers

It’s alright to have some strong preferences for your future partner, and very common. Creating a list of qualities and values you’d like in a potential dating partner is a wise step; it helps you figure out what’s important to you in a relationship. However, it’s essential to be mindful of one thing: having an overly long checklist can make it tougher to find the right person to date. Here’s a secret not everyone talks about: even if you do find someone who matches everything on your list, it doesn’t necessarily guarantee that special “spark” or chemistry between you two. 

For this conversation, though, when we discuss “dealbreakers,” we really mean the foundational things. But not so fast. In this polarized modern reality, having an open mind is a super power, and we can’t encourage that enough. Growth is born from discomfort. Misaligned ideologies paired with patience, respect, and open communication might make for some of the most satisfying and illuminating conversations of your life. Mixed race couples have challenges to face together which might offer each partner a new and truly multicultural perspective. Interfaith dating could lead you to test and expand your own spirituality. Dating someone who makes less money (or more money) might prompt an inventory of your lifestyle and values. And perhaps the biggest pill to swallow here: dating someone with different political views might provide you with a more empathetic and global understanding of the world around you, and if you’re convinced your way is the right way, might even help you see that with more depth and clarity.

If you’ve taken an inventory and are certain that there are some lines which cannot be crossed, that’s also okay too! We only recommend that you identify why. Sometimes our points of view are informed by bias and prejudgement, and we believe in seeing the individual for who they are, whenever possible. 

First Date Discussions

So, let’s say your person’s passed the deal breaker check and you want to dig in a bit. Deep first date questions can be refreshing, if delivered tactfully. 

Pro tip: a quick check-in with yourself, identifying what you might feel comfortable answering, might be in order before interrogating someone about their past relationships, who they’re hooking up with, family dynamics, finances and mental health.

The opposite of gravity is levity, and you’ll want a little more of the latter when you’re just playing for the first time in the sandbox together. Curiosity about them is a great thing, but consider creative and open questions rather than those which might be considered too personal or invasive. “How did your last relationship end” is charged, for example, and demands that they revisit a loss. A more simple “do you like to date?”, though, keeps them in control of their own narrative, but opens the window for more dynamic and less pressurized discussion. If you want to understand their upbringing without being invasive, you might say, “Tell me about your childhood hobbies and favorite family traditions.” This way, you encourage a glimpse into their past without going in hard and fast. Instead of asking, “Have you ever traveled abroad?”, you might try: “If you could wake up anywhere in the world tomorrow, where would it be and why?” This opens up a vibrant conversation about travel desires and aspirations. For a little more guidance, take a look at our list of good first date discussion topics. 

But I’ve GOT to KNOW!

Let’s say there’s some information looming that you didn’t manage to sift out before the date, and you’ve just gotta have it. Now.

Asking pointedly and honestly isn’t necessarily a taboo, but it will likely signal that the question bears a lot of importance to you and/or could feel like a test. If you’re comfortable with that, fire away, but if you want a little more subtlety: talk about you a bit. People often share their own experiences or viewpoints in response to what someone else is saying about their own as a way of building rapport or simply continuing the conversation. Thankfully, you’re often apt to receive information organically without the need to pry.

If you do go head-first, though, be ready to listen actively. Authenticity and a little vulnerability go a long way, and showing that person that you’re genuinely interested in their story and hearing them (rather than auditing them against a secret checklist) is likely to make them feel more comfortable to engage openly with those deep first date questions. 

The First Date of the Rest of Your Life

Your most spicy questions on a first date should remain just that: a little spice. A common pitfall for type-A daters (speaking from first-person experience, here) is to go on a fact-finding mission in order to quickly and loosely découpage an image of a person to assess the prospect of long term compatibility. Thankfully, in the human world, these things take more time than you have over margaritas and mozz sticks.

If you find yourself “interviewing” someone, we suggest changing the scenery for your future dates. Dating fatigue is real, and being sat across a table from someone telling the same story of your own life and asking the same questions, week in and week out, can make your own conversation stale, and possibly put you in a vicious cycle of tedium. There are things you’ll need to know about someone to stay with them, but your initial energy exchange might benefit from a more playful orientation. Consider an activity date: a hike, a paint-and-sip, or a museum trip. “Do you like this shade of blue?”, on day one, is likely more fun to ask (and answer) than questions about their view of the current administration and what they’ve done to heal themselves of generational trauma.