Playbook Guide 01 · Before the proposal

Pre-Season

The lead-up to the ask: readiness, alignment and a moment designed around your relationship.

The Principle

If your goal is long-term success and partnership with your person, it's worth feeling and thinking your way through an engagement well before the actual proposal. This is your "pre-season": an important time to develop readiness, alignment and confidence for a moment designed around enhancing your relationship.

The Essentials

1. When it matters. While there is no magic number for when to start preparing and planning, build in a conservative time estimate to allow for ample space before you propose. It's really a practical exercise. Type As may consider loosening up just a bit to avoid analysis paralysis and turning something beautiful into something rigid and stressful. Type Bs may want to make an extra effort to avoid coming off as nonchalant or last-minute. Whether you're planning to ask, expecting to be asked, or deciding together, the season starts here.
2. Check your readiness and alignment before you check the calendar. Having a perfect moment is secondary to ensuring it's a ready one: be honest with yourself about whether and how you've talked about a shared future, and that it's a choice from a place of shared confidence (as opposed to drifting into the next logical step).
3. Have key conversations first. Marriage, children, money, faith, careers, where you'll live, how flexible each of you are, and any "non-negotiable" things that you know deep down would fundamentally change how you show up in the relationship. While life is unpredictable, the big surprise should be the moment of the proposal and celebration.
4. Feel out how they want to be asked. Some people want a full surprise; others want to choose the ring together or know roughly when. Pay attention to your partner, and get to know people who know them well. Find out quietly, or simply raise it as part of your future planning and life-building conversations.
5. Choose the ring with intention. Learn their style through what they wear or a trusted friend. Set a budget you're comfortable with (don't get caught in the hype of going into debt for a flashy ring), get the size right, spend time comparing the vast combinations of materials out there, and ask about appraisal, insurance and resizing when you buy. Fun fact: rings with stones around the whole surface of the band are often harder to resize.
6. Consider family and tradition. If asking for a blessing matters to your partner or either family, plan that conversation. If it doesn't, skip it without guilt. Equally, if it matters to you personally, go for it. Also, if the family doesn't give its blessing, spend time really considering the impact that can have on the relationship, and whether you're both comfortable without that additional family support.
7. Design the moment in a way that's special for both of you. While the goal is to "get to yes," designing the engagement in a way that is memorable for both of you goes a long way and adds to the joy of the occasion. From a planning perspective, incorporate elements that play to your strengths, which will help with confidence and poise in the moment.
8. Decide whether and how to capture it. Similar to the notes above, decide how comfortable you and your partner would be in the public eye. To capture the moment in real time, finding a professional is a relatively easy service to coordinate and helps add nice polish to commemorate a major life milestone. Equally, a quiet moment between the two of you may be the right move. And you can then arrange for photo or video at a celebratory gathering, shower, engagement trip, etc.
9. Plan the logistics. How much time you may need to save for the ring and proposal activities, where the ring stays until the moment, a weather backup, travel timing, anyone you need to coordinate with for the surprise, what you both will wear, dinner reservations, photographers, etc.
10. Plan the first hour after. A dinner, a toast, the first calls to family and friends. The moment right after "yes" deserves a plan. This, too, should be customized to fit your relationship vibe.

Self-Reflections

Questions for honest self-assessment and curiosity to help build confidence as you progress through your groom season.

• Why now, and what am I choosing?
• What does partnership mean to me, and have we had transparent discussions about it?
• How would my partner want to be asked: surprise, involved, or somewhere in between?
• Private moment or people we love nearby?
• What would they want to be wearing, or ready for, if there are photos?
• What ring budget feels right without strain?
• Who can I trust to help, and keep the secret?
• What do I want to say?
• Even if they know it's coming, what little surprises can I layer in?

Potential Missteps

• Proposing before the key conversations have happened.
• Planning for social media instead of for your partner.
• Stretching too far on the ring to meet someone else's standard.
• Guessing the ring size and hoping for the best.
• Telling too many people, so the secret leaks.
• No backup plan for weather, timing or travel.
• Not knowing what you'll say when the moment comes.

Julian's Journey

Sharing tidbits from my own experience that may help discern your own confidence level:

How did you know it was the right time?

There are things we think about, things we feel, and things we know. On one hand, it's not often that we make major decisions from a place of 110% certainty. Life is risk and we do the best we can within that reality. On the other hand, people usually show you who they really are within the first 6–12 months of a relationship. That is a rule of thumb, but within that timeframe you have a pretty good grasp on a person's habits, preferences, good, bad and ugly.

For me, I of course paid attention to how my partner showed up, our chemistry, the fun we had together, alignment in life goals, and family and friend relationships and support. But I also examined how we handled conflict. In any instance of tension or disagreement, we have always come together closer and stronger than before. That dynamic, on top of everything else, created a sense of "knowing" and confidence in being ready to propose.

How did you choose Alexandra's ring?

That process was something we did together over a handful of weekends. And I'm glad we did, because my vision was quite different from hers. I think she would've been grateful and happy with my preconceived design, but she got to have substantial input to help guarantee she'd absolutely love the ring. That said, we didn't start shopping until we'd had a series of conversations about how we want to partner.

How did you plan the moment, and what would you keep or change?

Candidly, I invested a significant amount of planning, thought, and attention to detail for the proposal. But even the way I initially intended to propose changed over time and shifted pretty dramatically.

My original plan was to propose in Paris. I "sold" the trip as an anniversary celebration, but my partner was anticipating that, and I wanted to be a bit more spontaneous. So, I did some benevolent conspiring with her parents and a couple of friends to plan an unforgettable evening in Chicago (where we live).

I hired a boat for an evening river cruise and arranged for two stops along the river, including at an exclusive restaurant that was actually easier to dock at than secure a table.

Before the dinner, I picked her up on the river with champagne and macarons. As the boat set off, I started playing a playlist I made specifically for that evening. And I gave her a customized leather-bound journal in which I wrote and designed our story by chapters. By the end of the story, I was on one knee with the ring.

We then headed to dinner, where I had arranged for a professional photographer and a select group of people to celebrate with us. We then cruised the river and lake to close out the evening.

A few weeks later, we still went to Paris, took more pictures, and had a ball. But with the pressure turned way down since the proposal was behind us.

What did you say, or what do you wish you'd said?

I spoke (and wrote) from the heart. And I wouldn't change a thing.

Checklist

Tick items off as you go. Your progress stays on this device.

Make it yours

From the ask to the aisle.

The Curator is Grūm SZN’s premium offering: it helps you focus your priorities relative to how much time you have and moves with you along your journey. One-on-one sessions with Julian can be added à la carte (volume discounts available) for a bespoke service experience. A session can even help you plan the proposal itself: timing, the ring, the setting, logistics and thoughtful surprises, all discreetly.

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Grūm SZN shares personal experience and general ideas only. Nothing here is legal, financial, insurance or mental-health advice. For decisions like budgets, contracts or insuring a ring, talk with a qualified professional.