The Ultimate Guide: When to Propose


So you think you’ve found the one – the person that puts up with your quirks, laughs at your dad jokes, and indulges in the same hobbies as you. But now comes the big question: when should you propose? 

Proposing comes with a billion different emotions; you’ll feel excitement, anticipation, joy, nervousness, and even a fear of rejection sometimes. Before you start picking out the ring, let’s walk through some factors to consider to figure out when you should propose.

Understanding Your Relationship

Every relationship has its unique dynamic, and you’ll want to take a hard look at the depth of your connection and just how committed you are to each other before going for a proposal.

You can ask yourself questions like – Are we able to solve disagreements respectfully? Do we share common goals and wants in life? Are they emotionally supportive? Can I see myself spending the rest of my life with them? Why do I want to get engaged? These questions will help measure the strength of your relationship and the relationship’s readiness for an engagement[1].

Of course, it’s not just about answering these questions. It’s also looking for indications that you truly understand one another, respect each other, and have shared aspirations. These should be a lot more than simply having common interests or enjoying each other’s company. You should feel confident that the relationship can stay strong even during difficult times and that it’s more than a collection of peak experiences.

Relationships aren’t about reaching a state of perfection that you see only in movies – they should have a level of comfort and security, there should be a deep interconnection, and you should both cherish each others’ flaws and good qualities.

Signs That It’s the Right Time to Propose

Recognizing the signs that it’s the right time to pop the question can sometimes feel like reading tea leaves. But based on a survey with 3,100 responses, couples in the U.S. typically date for 13 – 18 months before getting engaged[2]. While time is one of the indicators, there are other markers that can determine when you should propose:

  • Open discussions about the future: While it’s fun and exciting to talk about your next holiday together or what dog breed you’d like to adopt, planning larger life decisions shows a deeper level of intimacy and trust. Whether it’s discussing career ambitions or starting a family, these deeper discussions show that you both see a shared future. In fact, when researchers have compared engagement proposals that were accepted versus rejected, people tended to reject proposals that came “too early” in relationships, before couples had these key convos[3]. 
  • Sharing financial goals: Money is a touchy subject, but if you’re able to have clear and honest conversations about it, it’s a healthy sign of readiness. Research suggests 70% of married couples argue about money more than anything else, so being open about it before an engagement can save many potential headaches down the line[4].
  • Emotional maturity: Being emotionally mature is important to a healthy relationship and involves a person’s ability to understand, manage, and express their emotions constructively[5]. Before an engagement, you should be able to navigate arguments without escalating them and show respect and empathy for each other’s feelings.
  • Living together: Two-thirds of married adults who lived with their partner before they got married say they saw living together as a step toward marriage[6]. Living together gives you a real idea of what it’s like to deal with day-to-day issues and compromises and potentially see sides of your partner you wouldn’t have otherwise. If you’ve successfully lived together, it’s a good sign! Just be careful that you aren’t just falling into marriage because it’s the next logical step after living together[7]

Signs That It’s Not the Right Time to Propose

Understanding the signs that indicate it’s not the right time to propose are just as important. Every relationship is unique and will have its own timeline, but there are some reliable  clues to watch for before deciding on an engagement:

  • Unresolved conflicts: Unresolved conflicts often point to a bunch of underlying issues. This might be different communication styles, deep-seated insecurities, or mismatched expectations. It’s no surprise, but if arguments tend to lead to resentment and bitterness, you’re not ready to take the next step[8]. It’s also not wise to use a proposal as a last-ditch attempt to save a failing relationship, as your partner may say no[9]
  • Lack of open communication: Effective communication is the foundation of any healthy relationship. It means you’re comfortable expressing your thoughts, goals, and fears and feel heard and understood. As poor communication is the number one reason why couples divorce, it’s recommended to improve on this factor before getting engaged[10].
  • Financial disagreements: Regular financial disagreements could be a sign you need to work on financial compatibility before a ring comes into the picture. Like communication, money issues are cited as a main reason for divorce[11]. And it’s more than just arguments about expenses and savings, it’s about different values and approaches toward money that could result in broken trust. Getting on the same page financially is key, especially since most couples merge finances when married[12].  
  • Different life goals: Among those surveyed in a Pew Research study, having shared interests was the number one factor of a successful marriage[13]. But as we’ve discussed, life goals go beyond that and include family planning, lifestyle preferences, and moral values. If you can’t find a balance, it could mean trouble and unhappiness later on. 

Navigating the Proposal Timeline with Cupla

Deciding when you should propose is complex. It requires understanding your relationship, evaluating when it’s the right time, and being mindful of red flags that suggest it isn’t the ideal moment yet. 

Relationships aren’t black and white, and there isn’t a “perfect” time to propose, but Cupla can play a role in maintaining your relationship with your partner as you move through your relationship journey. This relationship management app can foster open conversations on mutual goals as you set to-dos and reminders while you plan your life, help you spend more quality time together, and find space for each other in your busy schedules. 

Love isn’t just about that exciting proposal but an ongoing journey of nurturing and growth together. Let Cupla be your guide!

Cupla is a relationship management app for couples. With its user-friendly interface and innovative features including a shared calendar and to-do’s and date planner, Cupla empowers couples by providing tools for better organization, communication, and relationship well-being.

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