Creative Ways To Pop The Question: "Will You Be My Best Man?

Popping the question to your groomsmen is the easy part after finding the right partner. There are many ways to ask your friends to be by your side on your wedding day, and it's also an excellent excuse to treat them to something special. Whether you're searching for standalone gifts or want to curate your own proposal boxes, there are plenty of options to choose from. You can go for personalised items, such as engraved cufflinks, or opt for experience-based gifts like a round of golf or a gourmet dinner. If you're looking for something a little different, why not try a novelty tuxedo hoodie or a set of LEGO? Whatever you choose, make sure to add a personal touch to show your appreciation and excitement for the future.

Groomsmen proposal cards

Funny Cards:

• "No Strippers... (wink wink)"
• "Suit Up"
• "Free Beer"
• "Time to Suit Up"
• "Your Service is Requested as a Groomsman"
• "You're Going to be my Groomsman - Funny Groomsmen Card"

Formal Cards:

• "Will You Be My Groomsman?"
• "It's Time to Suit Up"
• "Will You Take a Shot at Being My Groomsman?"
• "Game On"

Personalised Cards:

• Customised with their initials
• Customised with their wedding role (e.g. Best Man, Groomsman, Usher)
• Customised with their name

Groomsmen gift boxes

Pre-filled Groomsmen Gift Boxes:

• The "Stud Set" from GroomsDay includes a personalised flask, black sunglasses, and dress socks with the label "Will you be my groomsman?" printed on the front. It is presented in a sleek black box with crinkle paper.
• The "Fashion Box Set" from GroomsDay includes trendy travel tumblers, which can be adapted in three ways (with a straw, a wide mouth, or a full-cover top) and can keep drinks hot or cold for hours.
• The "Sentimental Gift Box Set" from GroomsDay includes a personalised multi-tool with 10 different implements, including a knife, file, tweezers, scissors, and a screwdriver.
• The "Suave Squad Set" from GroomsDay includes a set of four monogrammed packing cubes made from lightweight, water-resistant materials with zip enclosures.
• The "Ultimate Box Set" from GroomsDay includes a personalised poker set.

Curated Groomsmen Gift Boxes:

• Cocktail groomsmen proposal boxes: Pair a bottle of bourbon with a gift box from Shaker & Spoon, which includes winter spice syrup, orange bitters, oil spray, and black cherries so your groomsmen can craft their own Old Fashioned at home.
• Alcoholic beverages: Include a bottle of their favourite alcohol, such as Fireball or Jameson, and pair it with shot glasses.
• Alcohol-free beverages: For non-drinkers, include a bottle of caffeine-free herbal tea, mini honey jars, ground coffee, or a Starbucks Breakfast Blend.
• Personalised items: Include personalised items such as engraved wooden watches, engraved cigar cases and cutters, custom golf balls, engraved pocket knives, or custom guitar picks.
• Practical items: Include practical items such as a beer cooler, a Dopp kit, a travel journal, a tape measure, or a set of packing cubes.
• Fun items: Add a novelty item such as a novelty tuxedo hoodie, a LEGO set, or a funny notebook with "Best Man Speech Notes and Jokes" written on the front.

You can also add a personal touch to each box by using plain black photo boxes and writing out the names of your groomsmen on card stock with watercolour pens. Fill the box with tissue paper and include a proposal sticker inside.

Groomsmen gifts

Gift Box Sets

A well-curated gift box is always a good idea. You can either build your own or purchase a pre-assembled one. These boxes can include a variety of items such as cufflinks, flasks, shot glasses, beer labels, wallets, and more. They offer a range of options to suit different personalities and interests.

Personalised Accessories

Add a thoughtful touch with personalised accessories like engraved watches, classy cufflinks, custom wallets, or even a stylish flask. These items not only serve as mementos of your special day but also remind your groomsmen of the bond you share.

Outdoor Enthusiast Gifts

For the outdoor enthusiasts in your wedding party, consider gifts like a hatchet and ammo can gift set, a survival knife, or a custom grill tool set for BBQ lovers. These gifts are both practical and unique, offering functionality and a memorable keepsake.

Audio Gifts

For the audiophiles in your bridal party, consider a custom Bluetooth speaker or a set of Bluetooth earbuds. These gifts will allow them to enjoy their music on the go, and the personalisation adds a special touch.

Barware and Drinkware

Drinking-related gifts are always a popular choice for groomsmen. You can opt for whiskey glasses, beer mugs, cocktail smoker kits, or even a personalised beer or whiskey gift set. For a non-alcoholic option, consider a Halo Whiskey Smoker Kit, which allows your groomsmen to create smoked cocktails at home.

Experiences and Activities

Sometimes, the best gift is an experience or activity you can do together. Consider taking your groomsmen to a sports event, a day at the races, or treating them to a gourmet dinner. These shared experiences create lasting memories and strengthen your bond.

Remember, the key is to choose gifts that align with the interests and personalities of your groomsmen. You can also mix and match items to create a unique combination that suits each individual.

Groomsmen proposal ideas

Groomsmen are pivotal to the planning and execution of pre-wedding events, offering support and ensuring the groom gets to the altar without a hitch. Asking your groomsmen to be a part of your wedding party is a special moment and a fun way to treat them to gifts that honour the occasion. Here are some ideas for groomsmen proposal gifts:

Gift Boxes

A pre-filled groomsmen proposal box can include goodies like a personalised flask, black sunglasses, and dress socks with "Will you be my groomsman?" printed on them. You can also build your own groomsmen box with items like engraved flasks, personalised cufflinks, or a custom illustration of you and your friend.

Alcohol-Related Gifts

Alcohol is a classic choice for a groomsmen proposal gift. You can pair a bottle of bourbon with a gift box so your groomsmen can craft their own Old Fashioned at home. You can also get creative with alcohol labels, such as "Chug to Accept" wedding proposal vodka cider bottle labels or custom whiskey labels.

Personalised Gifts

Personalised gifts are a memorable way to propose to your groomsmen. Custom golf balls, engraved cigar cases and cutters, custom dress socks, pop culture tie bars, and engraved wooden watches are all unique gifts that will be cherished for years to come. You can also gift personalised zippo lighters, which are not just for cigar smokers but can be useful in various situations.

Practical Gifts

Practical gifts are always appreciated, especially when they are personalised. Monogrammed handkerchiefs, engraved multi-tools, insulated coffee mugs, wooden valet trays, and packing cubes are all useful items that your groomsmen can use long after the wedding.

Fun Gifts

If you want to add a bit of humour to your groomsmen proposals, consider novelty tuxedo hoodies, LEGO sets, or working clock cufflinks for the friends who are always running late. You can also find funny cards with messages like "I need you, bro" or "There's only ONE thing BETTER than having you as my BROTHER."

Groomsmen proposal sets

The "Suit Up" Set

This set plays on the idea of your groomsmen suiting up for the wedding. It can include items such as:

• A "Suit Up" proposal card, which can be a simple and direct way to pop the question.
• A pair of dress socks with "Will you stand with me as my groomsman?" printed on them.
• A personalised bow tie or tie, adding a fun and stylish element to the proposal.
• Cufflinks, perhaps with a funny twist, like a pop culture reference or a fishing lure for the fishing enthusiast.

The "Cheers" Set

For the groomsmen who appreciate a good drink, this set can include:

• A personalised whiskey glass or beer mug, engraved with their name and their role in your wedding.
• A cocktail shaker and some fancy drink mixers, inviting them to craft their own cocktails at home.
• A set of whiskey stones, so they can enjoy their drink of choice without dilution.
• A funny drinking-themed card, such as "There will be an open bar" or "Your service as a groomsman is requested".

The "Grooming" Set

For the groomsmen who appreciate looking and feeling their best, this set can include:

• A personalised toiletry bag, filled with travel-sized grooming essentials such as cologne, shower gel, and a shaving kit.
• A stylish pocket comb, perhaps engraved with their initials.
• A set of fancy soaps or beard oils, for a touch of luxury.
• A card that says, "You're the groom's man, now go groom yourself!"

The "Memories" Set

For the groomsmen who have been by your side for a long time, this set can include:

• A personalised photo album or a scrapbook filled with memories of your friendship.
• A vintage-inspired card or a retro photo card, reminding them of all the good times you've shared.
• A gift that ties into a shared hobby or interest, like a custom golf ball set or a set of playing cards featuring their favourite baseball team.
• A heartfelt letter, expressing your appreciation for their friendship and their role in your life.

The "Fun and Games" Set

For the groomsmen with a great sense of humour, this set can include:

• A novelty tuxedo t-shirt or hoodie, adding a touch of fun to the proposal.
• A funny card, such as a "Will you join my wolf pack?" reference or a "Bro, do me a solid" request.
• A LEGO set or a small puzzle, inviting them to be a part of your wedding "crew".
• A personalised joke book or a set of funny groom-themed socks, for a light-hearted touch.

Frequently asked questions