What NOT to Talk About on a Date, According to Matchmakers

We’ve recently published a brief guide with suggestions for what you can talk about on a date. Key take-aways from that, in a modern world and with a suitable dating partner, might have led you to understand that the sky is practically the limit. We’re sticking to that, fervently, and adding to it here: with some carefully selected and qualified ideas on date topics to avoid.

Despite our position, there may indeed still be some first date conversation topics that you might avoid, and people have been advising on them forever. While we truly believe there’s some wiggle room for creativity and mindful discussion about almost anything, we’d love to visit some of those taboo topics and areas where you might best proceed with caution in order to better represent yourself and foster a sense of safety and interest between you and your date. Remember, successful conversation is an art form and a dance. Let’s make sure you’re wearing the right shoes.

Topics to Avoid Discussing on a First Date

Here’s a list of potentially sensitive and/or awkward conversations to avoid on a date, while still maintaining a genuine and engaging dialogue:

Controversial Political or Religious Discussions

We can only put a yellow “proceed with caution” flag on this one. While it’s best to avoid running toward potential conflict before getting to know someone and their communication style first, religion and politics are often deeply identity-based. Nobody expects you to drop who you are or your beliefs at the door, but the person across from you will have had their own journey with the topics, and you might prefer to spend some time on less intense discussions when you’re first saying “hello.”

Sensitive Cultural Matters

Be cautious about discussing sensitive cultural issues, stereotypes, or assumptions about your date’s background. This is sometimes more challenging than you’d expect, but it’s essential to respect each other’s diverse perspectives and cultures. Consider embracing open-mindedness and curiosity to learn about each other’s backgrounds without making assumptions or generalizations.

Personal Finances and Income

We can take a pretty hard position here and file this under “things you should never say on a date”—at very least, not a first date. Money matters can often be sensitive and deeply personal.  Avoid discussing personal finances, salaries, or debts, as it may cause discomfort and lead to you comparing yourselves financially to one another. We recommend focusing on experiences, aspirations, and interests instead.

Past Relationships and Exes

Your previous relationships and exes often inform how you approach dating, and you do not need to be ashamed to make space for these people and the impact they’ve had on your life. A best practice, though, would be to avoid having them leave an impact on your first date. Focus on you, and avoid the potential self-sabotage of getting mired in relationships that might not have ended the way you wanted.

Health Issues or Medical History

This information belongs to you and isn’t owed to anyone unless it’s for some sort of safety reason. Wearing your heart on your sleeve is one thing, but these conversations might also pull focus from other enjoyable conversations that enhance the dating experience.

Negative Experiences or Complaints

We want you to be you, and it’s okay to be grumpy sometimes. Maybe often. But if you’re wanting a fun time with your date, consider refraining from dwelling on negative experiences, grievances, or complaints about work, family, or life in general. Maintain an optimistic tone and emphasize enjoyable aspects of your lives.

Intrusive or Personal Questions

Respect personal boundaries and avoid prying into sensitive or intrusive topics such as family conflicts, past trauma, or personal secrets. Give your date space and time to share what they feel comfortable discussing.

Matchmaker Tip: some things might be more intrusive than they appear. For example, it’s relatively normative in queer dating to share coming out stories. For a lot of people, though, that’s a difficult subject–be careful, there.

Controversial Social Issues

Your position on controversial social issues might say a lot about who you are, and there’s no reason to hide that. Hot takes on current events keep us all glued to our screens for most of the day, though, and might distract you from getting to know each other as individuals. Tread lightly around highly controversial social issues that may lead to heated debates or differences in opinion, and if you do go there, know in advance that you might not be perfectly aligned on given issues. When it’s possible, concentrate on finding common ground and fostering a sense of connection.

Intimate Details

Consider saving intimate details about your personal life, relationships, or preferences for a more appropriate time when you know and trust each other a bit better. It’s okay to be forthcoming about the details of your life, but you might both feel more comfortable with sharing secrets a little further down the line.

Gossip or Negative Remarks

Remember: you’re making a first impression! Things you should never say on a date might best include gossip, negative remarks about others, or judgmental attitudes. You don’t need to be falsely positive, but 

These best practices aren’t all rules; they depend on you. As matchmakers at Tawkify, we know that compatibility with your match is predicated on mutual values, interests, goals, dealbreakers and lifestyles. With this in mind, we ask a lot of fundamental questions in our match screenings, including a few of these date topics to avoid. To boot, we conduct criminal background checks on all of your matches to add an element of safety.

If you haven’t been out with us, though, and you’re going it alone, you might indeed want to hit on some of these themes to get to know your person better. That’s okay! We just recommend a little forethought and sensitivity, which can be helpful in encouraging meaningful, enjoyable conversations that foster a genuine connection and understanding between both parties. Conversations to avoid on a date, fundamentally, are just the ones that impede establishing connection. 

Examples of Questions Not to Ask on a First Date

While we try to approach this pretty generally and with an open mind, we’ve also compiled a short list of gem questions likely worth avoiding for your consideration below:

How many sexual partners have you had?

You don’t need to know this.

How much money do you make?

You don’t need to know this today.

What do you pay for your home?

Invasive! New Yorkers might get a pass, here, though.

How has dating been, recently?

This distracts from the one you’re currently on. Focus on you two, in the moment.

Why are you still single?

This is a very simple question that might have a very complicated answer, and it might also just be a downer. If they’re not polyamorous, your date’s success really relies on the fact that they are still single. Embrace that.  Maybe they’re still single because they just hadn’t met you yet!

How was your pandemic?

How was yours? Try to keep our heads above water, when you can.

Ready for our final advice? Your date never has to feel like a pressure-cooker.

We know it can be nerve-wracking getting to know someone new, so take care of yourself and the person sitting across from you.