The Ugly Truth

1. Communication

• How do you prefer to handle conflict? Do you need time to cool off, or do you prefer to resolve things immediately?

• How do you feel about checking in with each other emotionally on a regular basis?

• What’s the best way for me to approach you when I have a concern or frustration?

• How do you usually express love and appreciation? How do you like to receive it?

• Have you ever felt unheard or dismissed in past relationships? What could have prevented that?

2. Money & Finances

• How do you view money—security, freedom, stress, or something else?

• What’s your spending vs. saving style? How do you feel about budgeting together?

• Do you believe in merging finances, keeping them separate, or a mix of both?

• How do you feel about debt? What are your financial goals for the next 5-10 years?

• What’s your opinion on financial transparency in a relationship?

3. Infidelity & Boundaries

• What do you consider cheating—physical, emotional, online interactions, or something else?

• How can we set boundaries to make sure we both feel secure and respected?

• How do you feel about friendships with exes or close friends of the opposite sex?

• What would help you feel reassured and confident in our relationship long-term?

• How should we handle situations where one of us starts to feel disconnected?

4. Intimacy & Emotional Connection

• What makes you feel most loved and connected in a relationship?

• How important is physical intimacy to you? How do you like to express affection? Do you like expressing affection publicly around others?

• Have you ever experienced a period of emotional or physical disconnection in a relationship? How did it impact you?

• How do you feel about discussing our needs and desires openly? Do you want me to express to you what I desire sexually and sensually in our relationship?

• What’s something small I can do that makes you feel wanted and appreciated?

5. Life Goals & Values

• What are your biggest personal and professional goals? How do you see our relationship fitting into them?

• How important is work-life balance to you? How do you handle stress from work?

• Do you envision living in one place long-term, or do you like the idea of moving?

• What does success look like for you in a relationship?

• How do you handle situations when your values clash with your partner’s?

6. Expectations & Responsibilities

• What are your expectations for how we divide household chores and responsibilities?

• How do you feel about traditional vs. modern gender roles in a relationship?

• What are some things your past partners have done that made you feel taken for granted?

• How do you think we should handle situations where one of us feels overwhelmed or unsupported?

• What’s something small that I can do regularly to make you feel appreciated?

7. Addiction & Habits

• How do you typically deal with stress? Do you turn to any habits for relief?

• Have you ever struggled with or been affected by addiction (yours or a loved one’s)?

• How do you feel about alcohol, smoking, gambling, or other potentially addictive behaviors in a relationship?

• How should we handle it if one of us develops a habit that negatively affects our relationship?

• What’s a healthy way we can support each other’s well-being and self-care? How do you want me to take care of my physical health, physical appearance, and overall well-being?

8. Conflict Resolution & Fighting Fair

• How did your family handle conflicts when you were growing up? Do you think that influenced how you deal with disagreements? Did your parents fight aggressively or did a parent walk away and ignore the other? What patterns of behavior do you think you picked up in the form of your fighting style?

• Do you think it’s okay to go to bed angry, or should we resolve fights before sleeping?

• What’s your biggest pet peeve when arguing with a partner?

• How do you feel about couples therapy or counseling as a way to work through problems?

• How can we create a safe space where we can express concerns without feeling judged or defensive?

9. Parenting & Children

• Do you want kids? If so, how many, and what kind of parenting style do you believe in?

• How do you feel about balancing parenting responsibilities between partners?

• What values and traditions do you want to pass on to our children?

• How do you think we should handle discipline, education, and other major parenting decisions?

• What’s something about your own upbringing that you’d want to replicate or avoid with your kids?

10. Family & In-Laws

• How involved do you expect your family to be in our lives and decision-making?

• What role do you think in-laws should play in a marriage?

• How do you feel about setting boundaries with family if needed?

• What’s your ideal way to spend holidays—together, separately, or alternating between families?

• Have you ever experienced family drama in a relationship before? How was it handled?

11. Growing Apart & Keeping the Spark Alive

• What’s something fun or adventurous you’ve always wanted to do together?

• How do you feel about scheduling date nights or intentional time together?

• What’s a way we can continue to learn and grow together over the years?

• How do you think long-term couples can keep the excitement alive?

• How do you want us to handle times when life gets busy, and we start feeling disconnected?

12. Conflict Prevention & Support

• What’s something I can do to make you feel supported when you’re having a bad day?

• How do you feel about apologizing—what makes an apology feel sincere to you?

• What’s a small issue that you think, if not handled properly, could turn into a bigger problem for us?

• How do you feel about relationship check-ins (e.g., sitting down every few months to discuss how we’re feeling about the relationship)?

• What’s one thing you wish more couples talked about before getting married?

1. Unresolved Emotional Baggage & Attachment Issues

• What childhood experiences have shaped the way I handle conflict and connection?

• Do I tend to withdraw when stressed, or do I seek reassurance? Why?

• Have I ever felt abandoned, rejected, or unworthy in relationships? How has that impacted me?

• Do I struggle with trusting others, or do I fear being too dependent?

• How do I react when my emotional needs aren’t met? Do I shut down, overcompensate, or lash out?

• What patterns from past relationships keep repeating? What role do I play in them?

• Am I fully aware of my emotional wounds, or do I avoid acknowledging them?

2. Poor Communication & Conflict Resolution

• How do I typically handle conflict—do I confront, avoid, or shut down?

• Do I feel safe expressing my emotions, or do I fear being misunderstood or judged?

• When I’m upset, do I communicate my needs clearly, or do I expect my partner to “just know”?

• Have I ever resorted to passive-aggression, criticism, or defensiveness in past conflicts?

• What is my biggest trigger in arguments, and where does it stem from?

• When was the last time I felt truly heard and understood? What made that experience different?

• How can I improve the way I approach difficult conversations?

3. Unmet Emotional Needs

• What makes me feel loved, valued, and emotionally secure?

• Have I ever felt emotionally neglected in a relationship? How did I respond?

• Do I rely on my partner for validation, or do I cultivate self-worth independently?

• When I feel lonely or disconnected, how do I usually cope?

• Have I ever prioritized external responsibilities over emotional intimacy? How did it affect my relationship?

• What emotional needs have I ignored or suppressed in past relationships?

• How can I communicate my needs in a way that fosters connection rather than conflict?

4. Clashing Core Values & Life Goals

• What are my non-negotiable values in a relationship?

• Have I ever sacrificed my values or dreams to accommodate a partner? How did that feel?

• Do I tend to prioritize security and stability, or do I crave adventure and spontaneity?

• How do I feel about financial management, career ambitions, and parenting? Are my views flexible?

• Have I ever felt fundamentally incompatible with someone because of life goals or beliefs?

• What is more important to me—finding a partner with shared values or learning to compromise?

• How can I ensure my next relationship aligns with my core values?

5. Power Struggles & Control Issues

• Do I struggle with giving up control, or do I let others take the lead too often?

• Have I ever dismissed or invalidated a partner’s thoughts or decisions?

• Do I subconsciously try to “fix” or change my partner rather than accept them as they are?

• Have I ever felt powerless in a relationship? How did I react?

• Do I view decision-making as a shared responsibility, or do I feel the need to have the final say?

• Am I comfortable setting and respecting boundaries, or do I struggle with them?

• How do I handle situations where I feel jealous or insecure?

6. Lack of Effort in Maintaining the Relationship

• Have I ever taken a relationship for granted? What led to that?

• Do I believe love should be effortless, or do I understand that relationships require work?

• How do I typically show love and appreciation in a relationship? Is it enough?

• Have I ever let routine or external stressors weaken my emotional or physical connection?

• What does effort in a relationship look like to me? Am I willing to give that consistently?

• How can I be more intentional about maintaining intimacy, communication, and connection?

• What small, meaningful actions could I take daily to nurture my future relationship?