GROOM: Clayton (Age 24)

BRIDE: Caille (Age 30)

LOCATION: Clayton and Caille are currently living apart but have spent time together in both Idaho and Iowa. They are now based in Cedar Rapids, Iowa, where they’ve been working seasonal sales jobs.

RELATIONSHIP DURATION: They have been officially together since October 1, 2024

ENGAGEMENT DATE: January 2, 2025

Clayton and Caille first met nearly three years ago while out dancing. Although there was an immediate spark, they remained friends for several years before deciding to pursue a romantic relationship. After spending an entire weekend together last fall, they quickly transitioned into a serious relationship. Just three months later, Clayton proposed during a New Year’s cruise to Mexico, even though they’d only been officially dating for a short time. Despite the rapid timeline, both felt confident they had found something meaningful.

While they share a deep bond and years of friendship as their foundation, their relationship has faced significant challenges. They began long-distance, living over 400 miles apart and learning how to stay emotionally connected without physical proximity. Once Clayton moved closer, new issues arose, including financial stress, frequent relocations for work, and the strain of adjusting to shared life after long periods apart. Both carry lingering trust issues from previous relationships where they experienced betrayal and heartbreak. Those past wounds have led to emotional walls and arguments in the present, sometimes leaving them feeling disconnected and uncertain about how to bridge the gaps.

Their relationship has been marked by a cycle of intense highs and difficult lows, including explosive arguments and periods of silence where unspoken tension hangs between them. Caille has at times questioned whether Clayton’s attention is fully on her, especially when he seems distant or preoccupied. She has even questioned infidelity. Clayton, in turn, has worries about whether Caille is truly committed to him or might see him as a fallback option. He had an ex who used him for money, so he’s hyper sensitive to being used. Both admit they’ve wondered if they’re staying together out of love, fear of being alone, or simply a habit.

Family and friends have expressed mixed reactions to how quickly the relationship progressed. Clayton’s family, especially his sister Mackayla, has raised concerns about whether he and Caille are truly prepared for marriage, given the speed of their engagement and the challenges they’ve faced. Caille’s mother, however, has been supportive from the start, giving the couple her blessing early on and trusting them to work through their struggles privately.

Despite the cracks that have emerged, Clayton and Caille remain committed to figuring out whether they are truly meant to be together. Both are eager for clarity about lingering doubts and hidden truths. They hope that by confronting uncomfortable questions and exploring their unresolved issues, they can either solidify their foundation or gain the closure they need to move forward separately. Ultimately, they want to know whether they’re building a relationship that will stand the test of time or if they are simply holding on to avoid letting go.

Example Questions From Caille to Clayton:

  • Have you ever cheated on me- emotionally or physically? 

  • Do you sometimes feel like telling me the truth could cost you my love or admiration?

  • Do you feel like I only want you when you’re being a certain version of yourself (funny, helpful, affectionate, etc.)?

  • Have you ever feared that being fully honest with me would lead to the end of our relationship?

  • Is there a part of yourself you think you’ll have to kill off in order to stay with me long-term?

  • Have you ever wondered if I’d still want you if you failed financially, emotionally, or spiritually?

  • Do you believe we’ve both used the threat of leaving—directly or indirectly—to gain power in the relationship?

  • Have you ever withheld affection or attention as a way to get back at me (even subtly)?

  • Is there something you’ve never told me—not because it would hurt me, but because it would change how I see you?

  • Have you ever confided in someone else about our issues in a way you wouldn’t want me to know about?

  • Have you ever suppressed your desires—sexual, spiritual, creative—so you wouldn’t rock the boat with me?

  • Are you actually fully committed to wanting to be here and be in this relationship?

  • Is Clayton keeping secrets about his childhood?

  • Is Clayton’s mother trying to break us up?

Example Questions From Clayton to Caille:

  • Do you still believe I’m the person you want to spend the rest of your life with?

  • Have you ever had doubts about our future together?

  • Do you feel emotionally safe when you’re vulnerable with me?

  • Have I ever hurt you in a way you haven’t fully brought up to me yet?

  • Do you ever feel like you’re compromising too much of yourself for the relationship?

  • Have you ever felt like walking away from the relationship during a hard time?

  • Do you trust me completely with your heart and your future?

  • Are there things about our physical or emotional intimacy that you wish were different but haven’t said?

  • Do you feel seen and appreciated for who you truly are in this relationship?

  • Are you in this relationship for financial benefit?

  • Have you ever lied to me about something you knew would hurt me?

  • Have you ever imagined being with someone else while we’ve been together?

  • Do you ever feel like you settled by choosing me?

  • Would you still be with me if I lost everything—money, health, or status?