Wedding
How to Plan a Holiday Engagement and Find the Perfect Ring at Dickinson Jewelers
Published: Nov 18, 2025
The holidays are one of the most magical times to pop the question. Twinkling lights, cozy weather, family gatherings — everything feels more meaningful. But planning a holiday engagement also brings its own challenges. At Dickinson Jewelers, we believe that finding (and proposing with) the perfect engagement ring should be as joyful as the season itself. Here’s a guide to help you navigate the process — plus a few local touches to make it extra special.
1. Start Early (Because ‘Holiday’ Means Everything Moves Fast)
2. Learn the 4 Cs
At Dickinson Jewelers, our team is well-versed in the 4 Cs (cut, carat, color, clarity), and we’re ready to walk you through them so you don't have to feel overwhelmed!
Cut — This affects how a diamond sparkles.
Carat — The weight of the diamond.
Color — How clear or colored the diamond appears.
Clarity — Whether the diamond has internal inclusions or blemishes.
Knowing your priorities among these (for example, “I want brilliance over size” or “I want a clean-looking stone”) will guide your choices.
3. Payment Made Easy: Layaway & Financing Options
Proposing over the holidays doesn't mean blowing your whole year-end budget. Dickinson Jewelers offers flexible payment options: you can use cash, major credit cards, in-store layaway, or financing (through approved credit).
Our layaway plan is especially useful for holiday engagements — you can put down a 20% deposit, make monthly payments (at least 10% of the purchase price), and pick up the ring when you’re ready.
4. Make the Ring Truly Yours
If you’re envisioning something more personal than a standard ring, Dickinson Jewelers offers custom design services. During the holiday season, designing a custom ring gives you something uniquely meaningful — maybe a band that reflects shared traditions, or a setting inspired by a special moment.
Because custom rings take time, planning early is even more important. Begin the design process well before your intended proposal date so you're not rushed, and you have space to refine details.
5. Prepare Your Proposal — With a Local Twist
6. After the Proposal: Ring Care & Next Steps
7. Why Choose Dickinson Jewelers for Your Holiday Engagement
Proposing over the holiday season creates a memory that extends beyond just a “yes” — it becomes part of your story. With thoughtful planning and the right support, your ring shopping can feel like an extension of the joy and warmth of the season, rather than something stressful. At Dickinson Jewelers, we’d be honored to help you make that moment unforgettable.
1. Start Early (Because ‘Holiday’ Means Everything Moves Fast)
- Inventory can shift. The holiday season often brings increased demand for engagement rings. Starting your search now gives you access to a wider selection, especially for popular styles.
- Book your appointment. While appointments at Dickinson Jewelers aren’t required, they’re highly recommended. One-on-one time with our stylists ensures you get expert advice, a relaxed experience, and personalized help. See more on the “Engagements Made Easy” page.
- Allow for resizing or custom design. If you’re starting with a setting or a mounting, and you want something custom, you’ll need extra time. Designing, ordering, and resizing all take time — and over the holidays, jewelers can get busier.
2. Learn the 4 Cs
At Dickinson Jewelers, our team is well-versed in the 4 Cs (cut, carat, color, clarity), and we’re ready to walk you through them so you don't have to feel overwhelmed!
Cut — This affects how a diamond sparkles.
Carat — The weight of the diamond.
Color — How clear or colored the diamond appears.
Clarity — Whether the diamond has internal inclusions or blemishes.
Knowing your priorities among these (for example, “I want brilliance over size” or “I want a clean-looking stone”) will guide your choices.
3. Payment Made Easy: Layaway & Financing Options
Proposing over the holidays doesn't mean blowing your whole year-end budget. Dickinson Jewelers offers flexible payment options: you can use cash, major credit cards, in-store layaway, or financing (through approved credit).
Our layaway plan is especially useful for holiday engagements — you can put down a 20% deposit, make monthly payments (at least 10% of the purchase price), and pick up the ring when you’re ready.
4. Make the Ring Truly Yours
If you’re envisioning something more personal than a standard ring, Dickinson Jewelers offers custom design services. During the holiday season, designing a custom ring gives you something uniquely meaningful — maybe a band that reflects shared traditions, or a setting inspired by a special moment.
Because custom rings take time, planning early is even more important. Begin the design process well before your intended proposal date so you're not rushed, and you have space to refine details.
5. Prepare Your Proposal — With a Local Twist
- Holiday gathering with family: If your family or partner’s family get together for Christmas or New Year, that’s a natural moment to propose. The warmth of familiar faces can make it feel even more intimate.
- A winter walk or lights display. Whether strolling the North Beach boardwalk or touring the Annmarie Gardens light display, there are some great Southern Maryland options! The soft glow of decorations is a perfect backdrop for a proposal.
- Cozy dinner followed by dessert: You could plan a dinner at home or at a favorite restaurant, then bring out the ring over dessert. You could even wrap the ring box as a "gift" to open together.
- Capture the moment: Have a friend or family member on standby to take a photo, or consider hiring a local photographer for a short session. You’ll want to remember not just the yes, but the way the season looked around you.
6. After the Proposal: Ring Care & Next Steps
- Sizing check: Fingers can swell or shrink a bit in colder weather — especially over the holidays when comfort foods, rich meals, and different routines come into play. If you weren’t 100% sure of ring size, now’s a good time to revisit it.
- Inspection and cleaning: We offer appraisals, repairs, and regular maintenance to keep the ring in top shape.
- Insurance: Once you have the ring, consider insuring it. If you need a professional appraisal, we provide that too.
7. Why Choose Dickinson Jewelers for Your Holiday Engagement
- We make the process easy, stress-free, and fun — no pressure, just expert guidance.
- Our staff is highly knowledgeable about diamonds and rings, so you don’t need to become an expert overnight.
- Flexible payment makes it more manageable to plan a meaningful engagement during the expensive holiday season.
- If you want something custom, we can design a one-of-a-kind ring that truly symbolizes your relationship.
Proposing over the holiday season creates a memory that extends beyond just a “yes” — it becomes part of your story. With thoughtful planning and the right support, your ring shopping can feel like an extension of the joy and warmth of the season, rather than something stressful. At Dickinson Jewelers, we’d be honored to help you make that moment unforgettable.