9 questions to ask yourself before you say “yes” to a relationship

Starting a new relationship can feel like standing at the edge of a cliff. When you think about it, that’s what it is – a new adventure. 

It’s thrilling, a little nerve-wracking, and who knows what you’ll discover, right?

But before you dive in, let me be that friendly voice in your head asking you to pause and reflect. 

Are you really ready for this leap? 

Here are some honest, soul-searching questions to ask yourself before saying “yes” to a relationship. Hopefully, they’ll give you some clarity as much as they did for me. 

1) Am I truly over my past relationships?

It’s funny, but a new relationship often requires us to look back before moving forward. I suppose that’s how it is with any self-improvement goal. 

The past is there to teach us lessons about ourselves. But it’s not a place to stay, especially if you’re with someone new. 

So ask yourself honestly if you’ve truly moved on from your past relationships. Lingering feelings for an ex can cloud your judgment and affect your new relationship. 

In fact, you may have moved on in the sense that you no longer love your ex, but what about anger? Hurt? Regret? 

Those are feelings to consider, too. If you’re still holding these in your heart, that could mean that there are still some unresolved emotions. 

It wouldn’t be fair to your new partner-to-be to carry that old baggage into your relationship. They’re a new person who deserves the fresh, baggage-free, completely-present, emotionally available version of you. 

That said, don’t forget to ask yourself this next question…

2) How well do I really know this person?

So, you’ve met this wonderful, wonderful person who makes your heart beat faster. Makes you see the world in rose-colored glasses. 

That’s great! But be careful – that could be the initial rush of infatuation and attraction talking. 

That’s all well and good if you’re casually dating. But if you’re deciding whether to enter a relationship with them, you’ll need to dig a little deeper. Get to know them a little bit more, beyond the surface-level interests you have in common. 

For example, how do they react to minor and major annoyances? How do they express themselves when something isn’t going well? 

What are their plans in life? What things give them joy? What’s their stand on issues that are close to your heart? 

And there’s a whole lot more to find out. So take the time to truly get to know the person, beyond the initial excitement. 

I know that entering a relationship involves the courage to take chances – after all, we can’t really get to know every single thing about a person even when we’ve been with them for a long time. 

But at least, do some due diligence and listen to your gut. You want a connection that’s based on more than just initial attraction.

Simply put, even when it comes to love, it pays to try and make as informed a decision as you can make. 

3) What are my personal goals and aspirations?

Just as much as you should know more about your partner, so should you know yourself, too. In fact, I’d say this is probably more important. 

Because when you know yourself, what you stand for, what your goals are…it becomes easier to choose a potential mate. It becomes clearer if you should “yes” to a relationship or not. 

This was a lesson I learned with one of my exes. Going in, I knew that our future paths were headed in different directions. 

His job involved a lot of travel, and as a teacher, mine required me to stay put. I ignored the thought that it would be hard to have a real relationship in a situation like that, and I insisted – we’ll make it work. 

News flash – we didn’t. We couldn’t. 

This experience taught me the importance of understanding what you want for yourself. Truth is, sometimes love isn’t the only deciding factor. 

4) Do our core values align?

This is the main point of why you need to get to know yourself and your prospective partner a little better beyond their looks and the feelings they inspire in you. 

Because in the long term, what will keep your relationship strong is the alignment of your core values. 

By core values, I mean the fundamental beliefs that guide our lives, like views on honesty, family, work ethic, and how to treat others. These are the principles that shape our decisions and actions. 

To give you an example, my husband and I have such different personalities and interests. On the surface, our relationship makes no sense. 

It will only make sense when you consider how compatible our core values are. We’re both family-oriented, hard workers, and we share similar ethical beliefs and life goals. 

You don’t have to agree on every little thing, but there should at least be a mutual respect and understanding for each other’s core beliefs. 

And believe me, even when you share similar core values, there will still be conflict. So it’s super important to flesh out your communication and conflict-management styles, too! 

5) Am I feeling pressured to say ‘yes’?

Really? In this day and age, people still feel pressured to go into relationships? 

Yes! 

Pressure doesn’t have to look like pressure (although if you come from an overly involved family complete with parents harping on their desire for grandchildren, you’d definitely feel that pressure 100%). 

Sometimes, though, pressure could simply take the form of envy, like when all your friends are coupling up and you’ve got no one on the horizon. 

And society does give us the message that we’ve got to be married/in a relationship by so-and-so age, as if you’d be a loser if you didn’t meet that timeline. 

Then there’s the internal pressure – the worry that time is running out to find someone, or the fear of being alone.

So it’s always worth asking, “Am I considering this relationship because I genuinely want to be with this person? Or am I just trying to meet someone else’s expectations or quiet my own fears?” 

Hopefully, you get an honest answer out of yourself. Otherwise, you could be putting yourself in a relationship for the wrong reasons. 

6) Do I feel comfortable being my true self around them?

Obviously, this question should be common sense, right? 

But – we’re strange creatures, aren’t we? We’re saddled with so many fears and anxieties!

“If they find out just how cranky/boring/corny I am, they’d be gone in a jiff…”

“If they saw me in the morning without makeup, they’d get their pants on like lightning…”

“[Insert other (imagined or real) unpleasant traits of yours] and there won’t be a relationship…”

See where I’m going with this? 

I’ve changed parts of my personality in the past just because I was afraid of rejection. And I’m sure I’m not the only one. 

My point is, before entering a relationship, make sure it’s one where you feel comfortable in your own skin. Going in with a facade or an image is just not sustainable. 

7) Am I ready to be vulnerable?

Being authentic also involves being vulnerable. That’s another good indicator if you should say “yes” to a relationship or not. 

You see, vulnerability might be frightening, but without it, all you have is two people showing only the parts they want to share. 

Not the complete picture. Therefore, not a complete connection. 

But if you’re willing to be vulnerable, that’s a good sign because it shows that: 

• You trust the other person
• You’re willing to take the risk

And you know what? With the right person, that risk will pay off. 

As researcher and writer Brené Brown puts it: “Staying vulnerable is a risk we have to take if we want to experience connection.” 

All this to say, if the thought of sharing your deeper thoughts and feelings makes you uncomfortable or anxious, it might be a sign that you’re not ready, or that perhaps this isn’t the right person or the right time. 

But if there’s hesitation, it’s worth exploring why before making a commitment.

8) How does this person impact my emotional well-being? 

Dating someone new can feel quite heady – one moment you’re up in the clouds, the next you’re down in the dumps or anxious as hell. 

Okay, that’s par for the course. But give it a little more time, then reassess. Notice how you feel after spending time with them. 

• Does being with them generally uplift your spirits or bring you down? 
• Do they bring you peace of mind or add to your stress? 
• Are they supportive during tough times? Are they happy for your successes?
• Do they respect your need for personal space, or do they tend to be overbearing or clingy?
• Is communication with them open and positive, or are there often misunderstandings and negativity?
• Does the relationship make you feel confident or inadequate? 

Ultimately, a relationship should positively influence your mental health, not detract from it. That’s something to say “yes” to! 

9) What are my expectations from this relationship?

Finally, what exactly are you looking for in a partner and in this relationship? Is it companionship, emotional support, shared goals, or something else? 

Like anything else in life, it’s always a good idea to flesh out your “why”?

Why? 

Because it answers another important question: Are you really in love with this person, or just with the idea of love?

When you’re clear on this, you save yourself and your partner a world of heartache. You’ll know if your feelings are rooted in reality or if they’re more about filling a void or fitting a societal narrative. 

Final thoughts

A new relationship can sometimes feel like you’re just rolling the dice, doesn’t it? But hopefully, taking the time to answer these questions honestly can get you closer to the right decision.

If nothing else, it will lead you to clarify what you want in a relationship, and that’s always a good thing!