• Dec 9, 2025

#26: Tough Questions to Ask When Considering Dating Someone

  • Pink Positive Dating

So you’ve hit it off with someone new—the chemistry is sizzling, the conversation is flowing, and the spark of a new flame might be igniting. But… how do you know if you should actually date this person seriously? Today’s episode is the perfect match for you, because we’re breaking down the exact questions to consider when thinking about whether or not to pursue a relationship with someone!

Life Vision and Lifestyle Alignment

Understanding and accepting a partner's lifestyle is crucial. You're not just dating the person but their lifestyle too. Do you enjoy how they spend their time? This can affect your relationship profoundly. For example, if someone prioritizes activities like marathon training that extensively fill their schedule, you might question how much space there’s left for a relationship. Consider if a partner's focus on a career, hobby, or goal leaves room for you and assess your own feelings about this.

Views on Marriage and Children

Discussing views on marriage and children early can prevent potential heartaches. Too often, couples avoid these discussions thinking they share the same perspective, only to later discover divergent views. It’s essential to know where you both stand on issues such as marriage and parenthood. Ask indirect questions about future life plans to get insights without applying pressure early on.  

Career Goals and Life Balance

Career ambitions can significantly influence your shared life path. Do the professional aspirations of your partner complement or clash with your own? Are you willing to support different levels of ambition or work-life balances? Reflect on whether hustle or travel aspects in a career align with your relationship goals and lifestyle preferences.

Financial Compatibility

Money isn’t just about numbers; it deeply influences lifestyle choices. Evaluate how potential partners view money and manage their finances. Discuss things like financial independence, attitudes towards debt, and strategies for wealth building. A shared vision of financial freedom can strengthen the foundation of your relationship.

Emotional and Mental Readiness

Emotional availability and mental readiness play vital roles in solid partnerships. Consider how potential partners handle stress or emotional discussions. Are they open and communicative, or do they resort to withdrawal or unhealthy coping mechanisms? Their willingness to consider help, like therapy, for unhealed trauma can also indicate engagement in emotional growth.

Love Languages

Knowing each other’s love language can enhance understanding and expression of affection in your relationship. Whether it's through affirmations, acts of service, or quality time, these expressions align with fostering a stronger emotional bond. Discuss and acknowledge love languages early on to feel seen and appreciated.

Core Values, Beliefs, and Identity

Shared core values and beliefs often serve as a guiding compass in relationships. Couples overlooking significant differences, like religious beliefs, eventually face challenges. Weigh the importance of issues like political beliefs, fitness routines, or lifestyle choices and discuss how they impact the relationship.

Conflict Style

Conflict is inevitable, but understanding how a partner handles it is essential. A partner’s approach to conflict resolution, openness to communicate, or how they manage disappointments reveals much about their relationship compatibility.

Relationship Intentions and Readiness

Intentions in dating can make or break future compatibility. It’s crucial to clarify if both parties see the potential for a serious relationship. Avoid investing time in someone unsure about their intentions, and ensure that your goals are aligned. Being upfront about your desire for a committed relationship prevents misunderstandings and aligns expectations.

The YOU Factor

Ultimately, reflect on how you feel about the connection. Does their presence bring joy, or do you feel the need to hold something back? Evaluate the mutuality of interest and your satisfaction with the status quo. Trust in your feeling about whether they fit into your life as envisioned.


Big Pink Question

Every episode ends with a Big Pink Question, a powerful reflection prompt to help you practically apply sentiments from today’s episode directly into your dating and relationship life in a transformative way. This episode's Big Pink Question is:

W hat are three important factors you want you and your ideal romantic match to be aligned on? It could be family planning, life goals, shared religion, discipline, financial goals, etc.?

Take some time to reflect or journal on this prompt. You never know what a good reflection will help you discover!


Affirmations

Affirmations are powerful tools you can use to transform your dating and relationship life, whether you're single and mingling or already in a committed relationship.

Affirmations are positive statements that you repeat to yourself to foster a mindset of positivity and self-empowerment by rewiring your brain to focus on a belief in your ability to accomplish your goals and outcomes.

These mental shifts reshape your internal dialogue, motivate you to take action, boost your emotional well-being, and offer you the strength to pursue goals despite challenges.

Follow@pinkpositivedatingon Instagram for daily affirmations to transform your love life. These affirmations can you help build confidence in your ability to find a suitable romantic partner, build a strong positive mindset to succeed at modern dating, and help you attract and strengthen romantic relationships.


Psst...Want to see some action? 👀 We're on YouTube!


Timestamps

Want to hear more about the points highlighted in the blog? Use the podcast timestamps to easily navigate to something you want to hear more about in the show!

04:17 Marriage and Children

05:53 Career Goals and Life Balance

08:13 Financial Compatibility

10:18 Relationship Readiness

11:26 Love Languages

13:00 Core Values

14:59 Conflict Style and Resolution

15:54 Defining the Relationship

19:03 The YOU Factor

20:28 Big Pink Question


Modern dating got you down? No worries.

Say bye-bye to settling for less and hello to dating success! Check out our free ebook on the ten steps to overcoming singlehood, settling, and situationships.

I'm in! Give me the ebook :)


Psst...wanna know a secret?

Whether you're searching for love or strengthening your relationship, we've got the secrets to help you meet your dating goals. Navigate the modern dating scene confidently with real conversations on topics that matter. You in?

Yes, I'm ready for all the tips!


Important Links

At Pink Positive Dating, our mission is to serve as a positive space for uplifting conversations of building happy healthy romantic relationships. Want to learn more? Check out the links below for insights, real conversations, and high vibes ✨

Next Steps

We hope you enjoyed you enjoyed this blog post! Don't forget to tune into the show, follow us on socials, and share this page with a friend! 😁

All Blog Posts