20 Questions to Ask Yourself Before Starting a New Relationship

Before entering a relationship, ask yourself the big (and hilarious) questions to ensure you're ready for love, quirks, and the occasional fight over pizza toppings. Here are 20 questions to ask yourself before starting a new relationship.

Alyana Aguja
November 19, 2024
5 min read

20 Questions to Ask Yourself Before Starting a New Relationship — Simone Secci from Unsplash

It’s not just about swiping right; it’s about getting to know yourself and what you need. By asking the right questions, you can embrace someone else’s quirks and survive awkward couple selfies and pizza debates. This can turn chaos into a thrilling adventure rather than a romantic trainwreck.

1. Do I like myself right now?

Giulia Bertelli from Unsplash

If not, then how do you expect someone else to like you? A good grounding in self-love means you are not looking for someone to complete you but rather someone to complement you. Plus, confidence is magnetic—own it!

2. Am I over my ex, or am I just pretending?

Kelly Sikkema from Unsplash

Dragging unresolved baggage into a new relationship is like wearing last season’s outfit—it doesn’t fit quite right. Make sure you are ready to move forward. Nostalgia is fine, but don’t let it sabotage your next chapter.

3. What am I really looking for: a partner or a distraction?

Victoria Roman from Unsplash

Be honest: Are you looking to connect, or are you bored and want someone to share memes with? Relationships take work, not just a Netflix partner. If you’re looking for entertainment, get TikTok instead.

4. Do I really have time for a relationship, or am I just idealizing what that could be?

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Love is fun, but it’s also time-consuming. It is a part-time job that pays in hugs and arguments. Don’t overpack your schedule with stuff where the real work of connecting must be done. Never be perpetually “too busy.” That’s no way to end. Neither of you will end up happy.

5. Am I ready to embrace someone’s quirks and flaws?

Girl with red hat from Unsplash

Spoiler alert: nobody is perfect, not even you. If you’re looking for perfection, you both will be headed straight for disaster. Can you accept their love of pineapple on a pizza or their obsession with conspiracy theories?

6. What’s my conflict resolution style: screaming, sulking, or solving?

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How you handle fights or arguments significantly affects your readiness for love. Relationships will test your patience, and you should expect misunderstandings and bumps. Are you a drama queen, a peacekeeper, or a problem-solver?

7. Am I willing to compromise on my favorite pizza toppings?

The Nix Company from Unsplash

Relationships are about compromise—and, of course, that includes pizza toppings. If you can’t give in to the little things, you probably won’t be able to make it happen with the big stuff. Love is having joy in decisions made together, even anchovies.

8. Do I even know what I want in a partner?

Oleksii Bocharov from Unsplash

You don’t go to the grocery store without a list, so why dive into dating without knowing what you’re looking for? Take some time to consider your non-negotiables versus your “nice-to-haves.” Clarity will make the search way less chaotic.

9. Am I prepared to meet some of their friends who might hate me?

Windows from Unsplash

Meeting the crew is daunting, especially if they’ve been burned. Prepare to win over that loyal BFF or skeptical sibling. Bonus points if you can charm the grumpy dog!

10. Am I cool with the impending embarrassment of couple selfies?

Nate Johnston from Unsplash

Love is full of cringe moments, from matching outfits to dancing with TikTok. Can you laugh at yourselves without spiraling into consciousness? Sharing awkwardness is half the fun.

11. How much of my past am I willing to reveal upfront?

Michał Robak from Unsplash

Your past has shaped you, but it doesn’t define you. Decide what you’re comfortable revealing and what can wait for later. Mystery is fine, but honesty is hotter.

12. Am I truly independent and willing to fight for that independence?

Denis Oliveira from Unsplash

A good relationship doesn’t mean merging into one person like some rom-com cliché. Make sure to keep your interests, friends, and routines. By the end of it, it is sexy to have a life outside of your partner.

13. What is my take on PDA?

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Some people love hand-holding, while others cringe at a cheek kiss in public. Know your boundaries and be ready to discuss them. There’s no correct answer, but mismatched PDA levels can be awkward.

14. Am I financially stable, or do I just want free dinner dates?

Vincenzo Landino from Unsplash

Money may be sensitive but discuss that, too. The reality is that dating doesn’t come cheap anymore—there are coffee dates, movie nights, and anniversary gifts. Discuss your financial level while things aren’t awkward yet.

15. Am I good at apologizing without sounding like a politician?

Michaela St from Unsplash

“I’m sorry you feel that way” isn’t an apology—it’s a cop-out. Practice taking responsibility for your mistakes. Genuine apologies can save a relationship from crashing and burning.

S O C I A L . C U T from Unsplash

Yes, this is important. Some people are excellent at giving you their last fry, while others will guard their food like it’s a national treasure. Can you compromise, or will it spark World War Snack?

17. How do I respond to jealousy: calmly, or catastrophically?

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Jealousy is a natural emotion, but if you let it run amok, it can turn toxic. Consider whether you’re prone to paranoia or trust issues.

18. Can I discuss my emotions without meming?

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Sharing memes is fantastic, but deep conversations tie a relationship together. If you can’t express your feelings verbally, work on them before getting into love. And no, sending a crying cat GIF doesn’t count.

19. Am I willing to listen to Spotify playlists that make no sense?

Tyler Lastovich from Unsplash

Chances are that music tastes get weirdly personal, and your partner may introduce you to genres you never knew existed. Prepare for lengthy car rides on folk-metal fusion or lo-fi whale sounds. You don’t need to like it, but you’ll probably learn to appreciate it.

20. Do I believe in love, or am I just jaded?

Mayur Gala from Unsplash

If you’re too cynical, you’ll sabotage the good things before they start. Believe that love can be messy, beautiful, and worth it. After all, the right relationship feels like the ultimate adventure.