There’s something undeniably magical about a Toronto proposal, whether it’s beneath the twinkling lights of the Distillery District, overlooking the city skyline from the Toronto Islands, or in a cozy corner of your favourite restaurant on King West.

The moment someone drops to one knee is life-changing, the kind of moment you'll replay in your mind a thousand times.

But here's what nobody tells you: before you get swept up in the romance, before you start posting those ring photos and fielding congratulations from everyone you know, there are some essential conversations you need to have.

Think of this as your pre-engagement checklist, a practical guide to making sure you're both on the same page before you dive into wedding planning and, more importantly, before you start building a marriage together.

Because here's the truth: spontaneity is romantic. The surprise proposal? Beautiful. The rush of excitement? Absolutely. But clarity is what builds a foundation that lasts. And realism? That's what turns romance into partnership.

Let's walk through what you actually need to discuss before you say "I do" or even before you start planning how you'll say it. Because the couples who do this work early? They're the ones who look back on their engagement as the beginning of something solid, not just something beautiful.

Start Designing Your Celebration

Have the Big Conversations First

Before the proposal happens, discuss your readiness for marriage and what it means to each of you. Ultimately, make sure you’re both on the same page and that each of your values align regarding your wedding, but most importantly, your marriage overall.

Be transparent about finances (this can be an uncomfortable topic, and that's ok!). You should understand each other’s financial situations and attitudes toward money and spending habits. Toronto’s cost of living is significant; understanding where you both stand helps set realistic expectations for engagement rings and wedding budgets.

Discuss your future lifestyle. Will you stay in Toronto long term? Do you envision a downtown condo or living the suburban life? These conversations reveal whether your visions align.

Claudia and Co. Proposal Tip

The best proposals surprise you in the moment, not the fact that you’re getting engaged. Discuss whether you prefer a grand public gesture or an intimate moment for two.

Talk about ring preferences. Your partner will wear this every day, so preferences matter. Silver or gold? Classic diamonds, lab-grown or coloured stones? These are all questions that should be answered prior to looking at rings for your future spouse.

Decide if you want professional proposal photos (with your partner ideally). Toronto photographers specialize in discreetly capturing these emotional moments.

Set Your Wedding Vision Early

Once engaged, questions flood in immediately. Having preliminary answers about timing, location, and size saves awkward “we haven’t decided” responses.

Discuss your ideal guest count and venue style. Do you envision a large venue like Liberty Grand? Or a smaller, more intimate venue such as the Cluny Bistro. Your numbers shape every decision.

Consider Toronto's seasons carefully when choosing your wedding date; each brings different advantages and challenges.

Summer offers beautiful weather but comes with premium pricing and limited venue availability since it's peak season. Fall brings stunning foliage and that cozy, romantic atmosphere (we're seeing incredible fall weddings right now, check out our blog on the trends we're loving this season). Winter can create logistical stress with unpredictable weather, though it offers a different kind of magic. Spring often has better vendor availability and more flexible pricing, plus you get those fresh blooms without the summer heat.

Navigate Family Dynamics and Expectations

Decide how you’ll share engagement news. Will you tell your parents first or announce it together? Navigate blended families sensitively.

Discuss cultural or religious traditions. Toronto’s diversity means many couples blend backgrounds, creating beautiful but complex celebrations that require planning.

Set boundaries about family involvement in wedding planning. Establish early who makes decisions and how much input you’ll accept.

Create Your Engagement Season Plan

Decide on an engagement party. Toronto offers stunning views from Yorkville dining rooms to rooftop patios with skyline views.

Consider engagement photos for save the dates. Evergreen Brick Works, Casa Loma, High Park and Kensington Market provide gorgeous backdrops.

Claudia and Co Proposal Tip

Start booking your key vendors, photographer, venue, and planner, within the first three months of your engagement, especially if you're planning a wedding during peak season (May through October in Toronto). The vendors you love most are often the first to fill up, sometimes a year or more in advance.

We always tell couples: don't wait until you have every detail figured out to reach out to vendors. Most professionals can guide you through the decision-making process, and securing your date with the right team is more important than having your color palette finalized.

One practical note: if you're considering a Saturday wedding in Toronto, start your search early. Fridays and Sundays offer more flexibility and availability, and they often come with better pricing, without compromising the experience.

Discuss Wedding Planning Logistics & Practical Concerns

Decide your involvement level. Will you DIY, hire a full-service planner, or find a middle ground? Toronto planners can make the process stress-free.

Establish your planning style. Does one person lead, or do you tackle everything together? Understanding your dynamic prevents frustration.

Planning a wedding can feel like a full-time job. Set boundaries to prevent burnout. Maybe no wedding talk during dinners, or limit planning to one or two evenings weekly.
Discuss name changes after marriage. This affects legal documents and professional identity.

Talk about living arrangements. Will you move in together post-engagement, wait until marriage, or are you already living together?

Consider honeymoon priorities and budget. International escape or a Canadian adventure? Factor in extra timing if planning a summer wedding.

Building Your Support Team

Planning a proposal is exciting, but it also involves logistics, especially if you want professional photography, a specific location setup, or coordinating timing without spoiling the surprise.

Your friends and family will want to help, and their support means everything. But proposal planning requires discreet coordination and vendor knowledge that most people don't have. That's where professional guidance makes the difference.

A luxury event planner helps you manage every detail without the stress. We coordinate with photographers, scout locations, handle permissions if needed, and ensure everything flows seamlessly, so you can focus on the moment itself, not the logistics behind it.

Planning your proposal should be exciting, not overwhelming.

Let us handle the coordination so you can enjoy the experience.

Start Planning Your Celebration

More Resources For Our Couples

How to Avoid a Tired Traditional Look: 5 Actionable Tips to Refresh Your Classical Wedding

6 Black-Tie Wedding Rules for the Guests Scrambling for Outfit Inspiration and Etiquette Questions

Why Portugal Is Your Dream Wedding Country & 5 Reasons You’ll Be Missing Out If You Go Elsewhere

At Claudia and Co., we specialize in luxury weddings and stunning proposals that stand the test of time, celebrations that people will talk about for years to come. If you’re looking for a wedding planner who can bring your dream wedding to life, let’s connect!