Dating can feel like trying to solve a Rubik’s cube while blindfolded. One day you’re head-over-heels, the next you’re questioning if they’re even on the same page as you.
We’ve all been there. Instead of waiting for your internal freak-out moment (we all know it’s coming), why not ask some key questions early on?
I know, I know, you’re probably thinking, “I don’t want to scare them off,” but trust me, getting clarity now saves you from waking up in six months asking yourself, “What am I doing here?”
These 9 questions are your toolkit for cutting through the BS early and getting a sense of whether your partner is worth investing more time in or if you need to make a swift exit.
1. How Can I Best Support You During Your Challenging Time?
Here’s the thing: at some point, life is going to serve you both a nice big plate of stress casserole—whether it’s a work crisis, family drama, or just good old existential dread. So, how do they handle it?
Do they shut down? Rage clean the kitchen? Or, do they text you 50 times in an hour looking for emotional validation?
I once dated a guy who, whenever he got stressed, became a human burrito—wrapped himself up in a blanket and scrolled through TikTok for hours. Problem was, I thought I was being supportive by constantly asking if he wanted to talk about it. Turns out, what he actually needed was silence and space.
Lesson learned: understanding how someone needs support will save you a whole lot of confusion and unnecessary “Are you mad at me?” moments.
2. What Do You Envision For The Future For Us?
This is one of those “rip the Band-Aid off” questions. You gotta know where they stand. Are they dreaming of a white picket fence and two toddlers, or are they more of a ‘let’s live in a van and adopt rescue dogs’ kind of person?
3. What Did You Learn From Your Past Relationships?
I’m all about learning from my mistakes, and I’m guessing your partner is too (I mean, hopefully, right?). This is your chance to find out what they’ve learned from their past relationships without feeling like you’re prying.
Maybe they regret not being more present, or they worked too much and missed out on important moments.
Sometimes it’s just about making sure you’re both conscious of what matters to each other so you can avoid falling into old patterns.
4. What’s on Your Bucket List Before Settling Down?
Before you settle into Netflix-and-chill mode forever, it’s super important to know what personal goals they’re working on. If they’ve got big dreams—like traveling the world, finishing a degree, or building a business—you don’t want to be the person who stands in the way of that.
I’ll never forget dating someone who said, “I’m gonna backpack across Southeast Asia for six months.” I thought it was a great idea . . . until I realized I was not invited.
But seriously, if your partner has things they need to accomplish before settling down, you want to make sure your timelines and priorities align. Otherwise, you might end up feeling like an afterthought in their life plan.
5. What’s Your Love Language?
Okay, this one’s basically like getting the cheat code for your relationship. Love languages are a real thing, people. You might think you’re being an amazing partner by buying them flowers, but if they’re all about quality time, those roses are basically invisible.
Get clear on how they feel most loved and make sure you’re speaking the same language.
6. If You Could Change Anything About Your Childhood, What Would It Be?
Let’s get deep for a second—everyone has stuff from their upbringing they either cherish or want to do differently. This question is gold because it helps you understand where someone comes from and how that shapes their future decisions.
Maybe they want to raise their kids with more open communication or avoid the mistakes their parents made.
7. How Do You Feel About Sex in a Long-Term Relationship?
Let’s not pretend intimacy isn’t a big part of a relationship. Whether you’re talking about physical connection or emotional closeness, it’s super important to figure out what your partner values.
I once dated someone who, after six months, revealed that they saw sex as just a formality in a relationship. Meanwhile, I viewed it as an important way to bond. If we had talked about it earlier, we could have avoided a lot of mismatched expectations.
8. Is There Anything About Me That Makes You Wonder About Our Future Together?
No one’s perfect. I mean, I’d like to think I’m pretty close (kidding . . . kinda), but everyone has quirks or habits that could be a concern for the future.
Maybe your partner thinks your five-alarm snooze-button habit is going to drive them insane, or maybe you’re worried about their tendency to shut down during arguments. It’s better to get this out in the open before those little things turn into big, relationship-crippling issues.
9. Is There Anything From Your Past That Could Impact Us?
Baggage. We all have it. What’s important is how much of it your partner is carrying and whether it’s something you can both handle together. Maybe they’ve got a difficult ex, or maybe they’ve been burned before and have trust issues.
Knowing what you’re up against can help you be more empathetic and avoid stepping on emotional landmines later.
Ask Now, Thanks Yourself Later!
Look, I know these conversations aren’t easy, and it’s tempting to avoid them because who wants to rock the boat, right? But trust me, if you really want to build something meaningful, these questions are non-negotiable. They’re your relationship insurance policy.
By asking these questions early, you’ll avoid a lot of the guessing games and relationship drama down the road. And hey, if the answers don’t align, it’s better to find out now rather than after months (or years) of emotional investment.
So go on—ask away. Your future self will thank you.
