Valentine’s Week isn’t just about one big moment, it’s about the build-up, the tiny gestures, the smiles that linger. And if your love happens to have included ice cream dates, stolen spoonfuls and inside jokes over cones, then a proposal at an ice cream shop Chicago couples adore, such as Big Bros Ice Cream, feels… just right.
Whether you’re a romantic who swoons over grand gestures or prefers soft, subtle romance, here are 7 proposal ideas to suit different personalities, different days, and different kinds of love, just right for celebrating valentines with a sweet Big Bros twist.
1. The “One Perfect Day” Proposal
For the classic romantic.
Not everyone wants a week-long plan. There are some people who believe that the best way to celebrate is to choose one glorious day and make a memory out of it, such as valentines day.
Keep it simple: a Valentine’s date, some flowers, a note, maybe a walk. End the evening at Big Bros Ice Cream. As you order, slide a small note across the table or ask the staff to hand over a cup with a message taped underneath:
“Will you be my Valentine… forever?”
It’s simple. No pressure. Just warmth, sweetness, and honesty, like the best kind of love.
2. The Valentine’s Week Countdown Proposal
For those who love anticipation.
This one’s for the planners and the romantics who enjoy suspense during valentines week.
Each day of the week, do something small,
a flower, a treat, a tiny surprise that feels thoughtful rather than overdone.
On the final day, bring them to Big Bros Ice Cream. Order two scoops. On the last spoonful, ask the question.
The message here is subtle but powerful:
“I choose you, not just today, but every day.”
3. The Flavor-Based Love Story Proposal
For couples who bond over food.
This is where Big Bros Ice Cream really shines, even if you’re sharing a scoop of vanilla ice cream in Chicago that feels familiar and comforting.
Choose flavors that represent your relationship, your first meeting, their personality, the chaos and calm you share. As you explain why you chose each flavor, end with:
“Just like these flavors, I don’t want life without you.”
Sometimes meaning melts hearts faster than rings.
4. The “Ordinary Day” Surprise Proposal
For low-key, deeply emotional lovers.
No decorations. No announcements. Just a normal day that turns extraordinary at an ice cream shop Chicago locals already associate with comfort.
You casually suggest ice cream. They think it’s just another date. While sitting there, mid-conversation, you pause and say:
“I don’t want this to be just another day. I want it to be the day I asked you to stay.”
That quiet shock, the soft smile, the teary yes, that’s the magic.
5. The Group-Friendly Proposal
For people who feel safer with loved ones around.
If your partner values friends and family, make it a shared joy, perfect even for galentines day vibes.
Invite close people under the excuse of an ice cream outing. Everyone orders scoops. Laughs happen. Photos are clicked. Then you stand up, nervous, real, honest.
You ask the question. Cheers erupt. Someone cries. Ice cream melts. Memories don’t.
6. The Long-Distance Reunion Proposal
For couples who’ve waited.
If you’ve been apart, this one hits differently, especially when it ends with something familiar like an ice cream truck Chicago couples often spot on nostalgic evenings.
After a long gap, keep the day light. No hints. End it with ice cream that feels grounding. As you sit together, say:
“We’ve already survived distance. I want to choose closeness with you.”
Soft words. Deep meaning.
7. The Big Bros Signature Flavour Proposal (Save This for Last)
For the dramatic finish.
This is the showstopper.
Pick a Big Bros signature flavor, the one they always order or the one you fight over every time. Ask the staff, if possible, to help with a small card or cup message.
When the ice cream arrives, let the question speak before you do.
Because some love stories don’t need speeches,
they just need the right flavor at the right moment.
Final Scoop: Love, But Make It Real
A proposal doesn’t need perfection.
It needs truth, timing, and intention, especially on valentines day, when emotions already run high.
Big Bros Ice Cream isn’t just dessert. It’s laughter after bad days, comfort after silence, and sweetness shared without reasons. And that’s exactly what love should feel like.
So whether you propose in one moment or across a whole week, make it you.
Make it honest. And let love melt naturally.
Frequently Asked Questions
Yes, proposing at an ice cream shop Chicago couples already love keeps the proposal moment intimate and stress-free. It’s relaxed, special, and exactly what you want if you want the proposal to happen naturally and not too formally planned.
Of course. An ice cream truck chicago proposal idea is a surprise and a fun memory that will be perfect for Valentine’s Day if your partner enjoys surprise and fun moments over formal ones.
Couples in Chicago opt for vanilla simply because it represents comfort, simplicity and undying love that is ideal to express what you feel without bringing stress or complications at a given moment.
Both are perfect. Valentine’s Day Week gives you a chance to build anticipation over little actions, while Valentine’s Day is good for people who don’t want more than one big moment.
Yes. Some proposal ideas, although romantic, can be used for galentines day, especially if you are celebrating love, friendship, or if you are planning a non-traditional proposal with friends.
