Five EASY (And Important) Questions to Ask by the Fifth Date

Are you asking the right questions?

If you Google “important questions to ask when dating,” up comes literally thousands of long, detailed results. Many will be lists of at least fifty questions to ask your date, and the number usually goes up when you search for Christian or Catholic questions. These lists are great to provide an overall idea of topics to cover, I think. But the problem is they’re usually REALLY intense if you’re only just getting to know someone!

So today I’m going to give you five easy, unique, and insightful questions to ask on those first five dates. Not only do they touch on important topics and offer insight to your date’s character, but they’re also low-pressure, socially-appropriate phrasing for early dating! There is no pressure, no jumping the gun, and of course, no compromising on your standards when you start with these questions.

So whether you’re tired of having dates turn into interviews . . . or you want to learn more about each other without needing a PDF reference list . . . or you simply want an easy jump-start to successful dates. . . this list is for you!

First Date: “What was something weird that happened to you this past week?” 

First dates are meant to be fun, short, and enjoyable, so ask questions in that same vein! While it’s not wrong to delve into deeper topics on first dates, it can put a lot of pressure on people who are still relative strangers. Questions like this are softball conversation starters, ease first date jitters, and can lead into fun discussions about your respective lives.

Don’t be afraid to throw out something way outside of the box when you’re answering it: maybe you have a cute story from work, or maybe your crazy great-aunt acquired yet another pet python. Who knows?! The fun is found in the extraordinary!

Second Date: “How would you spend a whole weekend of free time?” 

Again, much like first dates, second dates are still pretty surface-level interactions. It’s a good idea to start framing fun questions which will tell you more about your date than you already know from their profile online. How someone would choose to spend free time can tell you a lot about their character, for instance. A hard worker might start describing a project they’d love to do, or a family-oriented person might talk about the people they’d want to see.

On the flip side, you could discover big differences in interests or lifestyles, such as an outdoor adventurer where you prefer libraries and museums. Once in a while, you might strike upon someone’s bad habits, like drinking or binging video games, which could be a red flag.

Third Date: “When you were growing up, what was a quality or trait your family valued?”

If you’ve made it to the third date, you probably have quite a bit in common and a mutual attraction to each other. So this is a good time to start asking questions about your backgrounds and families of origin. This particular question focuses on the overall experience of childhood, but leaves plenty of room to talk about specific events that shaped your date’s sense of self.

Did their rural family prize independence and faith? Perhaps education or responsibility was instilled at a young age? Maybe your date’s single parent valued a strong work ethic, or maybe a parents’ divorce upset the balance of childhood entirely. Wherever this question leads can teach you a lot about your date’s background, family, and what values they inherited along the way.

Fourth Date: “Tell me something important I don’t know yet.” 

You can tailor this question to your personal standards, by the way. Maybe you say “tell me something about your faith I don’t know yet” or “what’s something you want me to know, but haven’t told me yet?” The fourth date is often when couples are considering becoming exclusive, so it’s appropriate to open the floor to potentially intense conversations. This could turn into discussing past relationships, religion, careers, politics, or anything else you and your date finds important.

The key to using this question in a productive way is to turn on your active listening skills. You might get an answer way out of left field, or you might hear something you suspected all along. Whatever the case, this is the time to learn more deeply about each other, and offer your date the chance to bring up anything really big that hasn’t come up naturally in conversation before..

Fifth Date: “How do you see our relationship fitting into the future?” 

This is far more than the typical “what are we” talk, or the “do you want to get married one day” question. By date five, most people become an exclusive couple. If you haven’t had the exclusivity conversation by now, this question leads into the topic without being pushy. And if you are exclusive already, this is a great way to start communicating about your expectations for this new serious relationship!

Keeping this question open ended helps your date express his or her own thoughts in response, instead of prompting a binary “yes” or “no.” This question pointedly doesn’t include any premature talk about wedding planning or a future marriage, either. (If marriage comes up and you’re both mutually interested in discussing it, great! I’m just saying, don’t put the cart ahead of the horse: what you’re looking for here is some clarity and understanding of what the other person is expecting, not a proposal.)

Okay, but . . . what if your date gives you an answer you really don’t like? 

Sometimes these questions can lead to dud, or worse, straight up ugly answers. Ouch. The first thing to do when you get a response you don’t like is to not take it personally. The first few dates, and these questions, are tools to learn more about each other. They’re not a pass/fail pop quiz!

Especially if one of your more serious questions leads to a major surprise, consider it a good thing you asked about it this early. You have freedom to reflect and explore whether you have discovered a dealbreaker, a red flag, or potentially a no biggie. Why? You are taking time to get to know each other before you commit to pursuing a romance together, in order to make an informed choice.

Lastly, a huge part of asking these questions is to have answers of your own ready. Dating is give and take, and it’s only fair to volunteer similar information about yourself if you want the same information about others. So whether you’re asking for a funny story about work, or you’re discussing a sexual past, be prepared to talk about your side of things, too!