Best Sellers
Day Of Accessories
Gift Type
Bachelor Party
Groomsmen Proposal Cards
Ask the question in a way he will not see coming. Personalized groomsmen proposal cards that make the ask official.
You have known these guys through every version of yourself, and now you get to ask them to stand next to you on the biggest day of your life. A proposal card makes that moment land. Hand him something with his name on it, watch him read the line, and let it hit. Every card and box here is personalized free with his name or nickname, printed and finished by hand in our shop in Monroe, Connecticut, and ready to ship in 1 to 2 business days so you can ask your whole crew this week.
Free personalization on every gift
Engraved in-house in Connecticut
Ships in 1 to 2 business days
Not sure where to start?
If you want one gift that does the whole ask on its own, go with the Mustache Groomsman Proposal Box. It arrives looking like a real present, opens to the question, and gives him something to keep on the shelf long after the wedding. It is the pick for the friend who would actually be a little hurt by a plain card.
For the group that turns everything into a toast, the Suit Up Shot Proposal pairs the ask with a personalized shot so you can pop the question and clink glasses in the same breath. It is the easy yes for the buddies who bond over a good drink and a bad joke.
Browse Groomsmen Proposal Cards by Type
Once the yes is in, here is where to look next for the real wedding day gift.
How to Choose a Meaningful Groomsman Proposal Gift
The best proposal card is the one that sounds like how you two actually talk. Match the tone and the format to the friend, not to a trend, and the ask does the work for you.
Match the humor to the man. For the buddy who lives on inside jokes, a funny card like the Pop That Bro-Posal Card gets a real laugh. For your brother or your best man, lean sincere so the moment carries weight.
Decide between a card or a box. A card is quick and personal for a group ask. A box like the Groomsman Proposal Box gives him something to unwrap and keep, which reads as more of an event for your closest guys.
Personalize with the name he answers to. Use his nickname, not his legal name. Seeing what only the crew calls him is the small detail that makes him realize you actually thought about the ask.
Why the ask deserves more than a text
You are about to ask these guys to buy a suit, plan a trip, and stand up in front of everyone you know. A group text gets a thumbs up. A personalized card gets a photo sent to the group chat and a story he tells at the reception. The way you ask sets the tone for the whole thing, and a gift he can hold makes him feel chosen instead of just cc'd.
How Much Should You Spend on a Groomsman Proposal Gift?
The proposal is the opener, not the main groomsman gift, so most guys spend a little here and save the bigger budget for the wedding day present. Here is a simple way to think about it.
$25 to $50
Asking a full crew of five or more
Personalized proposal cards and shot sets like the Will You Be My Groomsman Proposal Card keep it personal without stacking up across the whole group.
$50 to $100
Your best man or a couple of core guys
Step up to a proposal box or a light-up cigar ask that gives him something to keep and marks him as one of the inner circle.
$100 and up
The brother or best friend you want to go big for
Pair the ask with a keepsake he will use on the wedding day, like an engraved decanter or a personalized watch, so the proposal and the gift arrive as one.
Who Are You Shopping For?
Your best man. He gets the biggest ask, so make it feel that way with a proposal box or the Top Groomsman Proposal. Then look at cufflinks for his wedding day gift.
The whole crew at once. Keep the format consistent so nobody feels ranked. A matching set of personalized cards asks everyone in the same tone and looks great lined up in a photo.
The friend who loves a drink and a laugh. Go with a shot or booze themed ask, then set him up with whiskey glasses for the toast at the reception.
The brother you have no words for. Skip the joke and let a clean, sincere card carry it. Sometimes his name and one honest line is the whole message.
Every proposal card and box is personalized free and finished by hand in Monroe, Connecticut, then shipped in 1 to 2 business days.
Order early so every guy has said yes before the deposits, the suit fittings, and the trip planning begin.
Frequently Asked Questions
What is a groomsmen proposal card?
How do you ask someone to be a groomsman?
Can I personalize these proposal cards for free?
Should the best man get a different proposal than the groomsmen?
What goes well with a proposal card as the real groomsman gift?
How long does delivery take?
Most orders ship out of our Connecticut office within 1 to 3 business days. From there, delivery time depends on where you're located.
Customers closer to the Northeast typically receive their orders faster, while those further away can expect a few extra days in transit.
What is your return policy?
We want you to love your purchase. If something isn't right, reach out to us within 30 days of your order and we'll do everything we can to make it right.
Because personalized items are made specifically for you, we're unable to accept returns or exchanges on customized orders. However, if we make an error on your personalization, we will replace the item at no cost to you, no questions asked.
For non-personalized items, we're happy to accept returns within 30 days as long as the item is unused and in its original packaging.
Let customers speak for us
vicki FOWLKES
Cleat Bag - Amazing!
I ordered these and paid for expedite shipping. I ordered 6 of them and they all came in within 4 days and look sooooooo good! Great quality and timely order, what else could you ask for! I was scared of the timing on these being ordered and receiving them, but I had nothing to worry about.
Cleat Carry
Arthur Wilson
Very impressed
I ordered 6 build your own groomsman boxes and once I got them and was able to look them over I am impressed. They are bigger than I expected but great quality. I would definitely recommend to any one that need to get gifts for your groosman.
Build Your Own Groomsmen Box
Jonathan McGuire
Monogrammed travel bags!
I had to order some unique gifts and all I could find were cigar and alcohol related items! But GroovyGroomsman had these totally 100% quality - monogrammed and sturdy as all get out. This is a bag you can be proud of! Small enough to fit on your seat and still hold what you need for the weekend! But with confidence and pride!
Heavy Duty Duffel
Evan Adelman
Well made
Got these for my brother’s bachelor party for all the guys. They are very well made. My only thing I would say is that they are thick for golf ball markers. I would consider cutting them down about half the height of what they are. We are all big golfers and they would interfere on the greens if you use them. Just my honest opinion. But they came out great and shipping was quick! Thank you for making them!
Copperlinks Custom Golf Ball Marker
Gregory Chambers
The quality of the product is as described. The customer service is fantastic.
Twist and Shoot Personalized Flask
T. Carlton
Loved by everyone!
My husband got this for his groomsmen a few years ago but was silly and didn't get himself one. His friends all loved it and would bring it on group trips and talked about how it's their go to bag. I finally ordered him one so he could enjoy it too!! The bag holds up well and carries lots of stuff! Many of the guys pack for themselves and their wives in just that bag.
Muscle Duffle
Victor Flores
Awesome Groomsmen Gifts
I gave these to my groomsmen and they loved it. Most said they will display in their offices as a good conversation piece!
Splendid Splinter Personalized Baseball Bat
Conlan Danieu
Great price, even better quality
And they got here within 3 days when I ordered 5 days before my wedding. So happy with these!
Elite Pour - Set of 5 Groomsmen Decanter Gifts
Matt Guza
Durable duffel
I was impressed with the delivery time, considering my order included 7 uniquely monogrammed duffel bags. Great looking product, seems quite durable and useful - served as a great groomsman gift after I had been searching for something other than stereotypical cigar containers and flasks. I consider myself a very satisfied customer!
Muscle Duffle
Carlos Gonzalez
Great service
Only problem was the bags had a strong musty/mildew odor. I had to place the bags outside for a several hours and add dryer sheets to the inside. Very disappointed in the odor. But the service, the box's and everything else was top notch!
The Gentlemen's Duffle
Ryan Bleull
Fantastic Groomsmen Proposal Box
I have seven groomsmen in my wedding next November and every single person LOVED this box! It made it so easy doing something thoughtful and easy to order when everyone is spread out. 10/10 would recommend!
Golfer's Dream Accessories Gift Box
Brenda Paupst
Great Duffel
This is a great canvas, Duffel. Very sturdy material and cleverly designed. It looks great...down to business looking.
Heavy Duty Duffel
Jake Buhring
The pictures don't do it enough justice
When I opened the package after receiving these, I was surprised how well crafted they were. The engraving was very nice, a lot of attention to detail. The shipping was fast and easy no problems with the item at all.
Aged To Perfection Decanter
Kurt Giuliani
Last minute purchase - made my day!
We purchased these socks for myself, my groomsmen and my father as a last minute decision. The delivery was super fast and made it just in time! The socks were pretty comfortable for all day wearing and my wedding party now have a great memento of the day!
Wedding Party Socks
Jonathon Basham
Best investment ever!!
From The most amazing customer service, to picking out the best gift, to delivery, I very much was very pleased and so was my best man.
No regrets what so ever.
Pal Capone Groomsmen Gift Set
