Dating can feel like trying to solve a Rubikโs cube while blindfolded. One day youโre head-over-heels, the next youโre questioning if theyโre even on the same page as you.
Weโve 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, youโre probably thinking, “I donโt want to scare them off,” but trust me, getting clarity now saves you from waking up in six months asking yourself, โWhat am I doing here?โ
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?

Hereโs the thing: at some point, life is going to serve you both a nice big plate of stress casseroleโwhether itโs 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 burritoโwrapped 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 โAre you mad at me?โ 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 โletโs live in a van and adopt rescue dogsโ kind of person?
3. What Did You Learn From Your Past Relationships?

Iโm all about learning from my mistakes, and Iโm 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 itโs just about making sure youโre both conscious of what matters to each other so you can avoid falling into old patterns.
4. Whatโs 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 theyโre working on. If theyโve got big dreamsโlike traveling the world, finishing a degree, or building a businessโyou donโt want to be the person who stands in the way of that.
Iโll never forget dating someone who said, โIโm gonna backpack across Southeast Asia for six months.โ 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 oneโs basically like getting the cheat code for your relationship. Love languages are a real thing, people. You might think youโre being an amazing partner by buying them flowers, but if theyโre all about quality time, those roses are basically invisible.
Get clear on how they feel most loved and make sure youโre speaking the same language.
6. If You Could Change Anything About Your Childhood, What Would It Be?
Letโs get deep for a secondโeveryone 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?

Letโs not pretend intimacy isnโt a big part of a relationship. Whether youโre 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 oneโs perfect. I mean, Iโd like to think Iโm 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 youโre worried about their tendency to shut down during arguments. Itโs 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. Whatโs important is how much of it your partner is carrying and whether itโs something you can both handle together. Maybe theyโve got a difficult ex, or maybe theyโve been burned before and have trust issues.
Knowing what youโre up against can help you be more empathetic and avoid stepping on emotional landmines later.
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