Get Them To Say “I Do”: 19 Groomsmen Proposal Ideas

Sure, you can just send an email or text message, but why not try more creative ways to make a groomsmen proposal? Here are some questions to keep in mind when thinking of proposal ideas for your groomsman:

  • What are his hobbies and interests?
  • Is there something he has been looking for but doesn’t have yet?
  • Can you picture him using this groomsmen proposal gift?
  • How customized do you want these gifts to be?

Still unsure what to get them? Here are 19 memorable groomsmen and best man proposal ideas, whether they’re gifts or special events. These unique suggestions and third-party products will get your potential groomsmen to say “I do” for sure!

19. For The Party Animals – The Shoot Your Shot Set

We all have a group of friends that are the life of the party. If your manpack happens to be the feisty crowd, give groomsmen proposal gifts that celebrate that spirit. 

This set offers free personalization for the flask, box, and shot glass. It’s a complete drinking set that they can use at your bachelor party, cookouts, or weekends away – great for groomsmen who enjoy getting buzzed!

18. For The Sentimental Guys – Personalized Pint Glasses

Customized glasses are always a meaningful groomsmen proposal idea, but why stop at a custom label? Take “personalized” to another level and give them a special pint glass, each one engraved with their photo.

Look for funny photos of the best man and groomsmen on social media, and pick the best ones to get engraved on their glasses. Add their nickname to the glass for a personal touch. It’s an original groomsmen proposal gift that all the guys will love!

17. For Homeboys Who Are Homebodies – Comfy Groomsmen Proposal Socks

People seriously underestimate how important socks are to a man’s wardrobe. They’re key for keeping warm and coordinating an entire outfit. Personalized or goofy socks are especially treasured in a guy’s closet, so why not give these comfy accessories as a groomsmen proposal gift?

These black dress sock sets are great gift ideas for Father’s Day or a groomsmen proposal. Spring for a custom groomsmen gift box and send them to your best friends and family members. No cold feet will be seen at your wedding party when your friends wear these thoughtful tokens!

16. For The Sporty Set – Catch A Sporting Event Together

To many guys, there is no better bonding activity than cheering on your favorite teams. Get tickets to a game for yourself and your friends. Send the tickets to them, along with a simple groomsmen proposal inviting them to join your wedding entourage. Drinks, snacks, and congratulations all around while you root for your favorite players – sounds like the perfect day out with your boys!

Can’t get seats together? Watch a scheduled game on your big screen at home instead and have a massive feast! Make it special with this groomsmen proposal idea: custom beer labels for the drinks you’ll be enjoying that day. Each label can have your wedding date and the names of your groomsmen and best man.

15. For Your Drinking Buddies – Send Insulated Koozies

These insulated drink koozies are a great groomsmen proposal idea from a small business! Each groomsmen proposal box comes with a cooler and message. You can pick the wedding title to include, whether it’s best man or groomsman. It’s a simple, practical gift that they can use for your bachelor party, birthdays, and other special get-togethers.

14. For The Rugged Outdoorsmen – Go On A Camping Trip

If you and the boys like to rough it, take them to Mother Nature for your groomsmen proposal! Plan a short weekend away to hike and camp out. Go fishing, swap stories, or simply chill out and catch up with each other. The woods will give you guys the time and space to reconnect without any distractions.

When you’re gathered over smores and taking swigs, give each of your friends a groomsmen proposal card with their favorite drink or snack for the great outdoors. It’s an unforgettable groomsmen proposal idea for nature lovers!

13. For Friends With A Funny Bone – Get Down On One Knee

Sometimes, the best groomsmen proposal ideas are the most obvious, yet creative ways. If you can pop the question to the love of your life over flowers and sweet nothings, you can do the same for your friends! 

Make it a lighthearted occasion at a formal dinner with all the works and really lean into the pseudo-proposal idea. Get down on one knee, say a few words about how they’ve changed your life, then ask them to be your groomsman or best man. Feel free to get a little emotional – it’s not every day that you’ll get the chance to show your boys how important they are to you.

If you want it to be truly spectacular, incorporate a song and dance…or even hire a flash mob! It’s up to you to decide how big a spectacle you want. Don’t forget to take a video of your big groomsmen proposal so you can all rewind and laugh about it later!

12. For The Bad Boys – Go For A Pub Crawl

Why wait until the bachelor party to have a rollicking good time with the boys? There are plenty of cities that have scheduled pub crawls, providing great drink deals for groups out to stay late and cut loose. Many of these crawls also have food and beverage deals that allow you to sample the best of each stop.

No pub crawls in your place? No problem! Make a list of your favorite haunts for a cold one, and plan a whole evening of strong drinks and good times! Celebrate with a toast at the first bar you visit and make that groomsmen proposal – it’s a happy request that will put everyone in a festive mood!

11. For The Classy Kings – Relax At A Cigar Lounge

Invite your friends to a cigar lounge to appreciate fine tobacco and talk about the good old days in a private space at the same time. It’s the perfect chance to bond over memories without any distractions. You can then give them a personalized cigar gift set, each with a groomsmen proposal card.

Not sure what to write on your note? You can still ask them through this personalized groomsmen gift: talk to the lounge proprietor and have personalized labels on each gift cigar’s stogie. This is a simple and meaningful way to ask them to be part of your big day.

10. For The Music Men – Go All Out At A Karaoke Bar

This groomsmen proposal idea is the perfect opportunity to belt out your favorite tunes with your boys. Leave the shyness at home and sing with zero shame at a nearby karaoke bar. With encouragement and a little liquid courage, everyone will be ready to take the mic.

Every group has songs that remind them of special times together, and it’ll be a blast to sing them all together. Pick a moment in the night to sing a cheesy romantic ballad or your group’s anthem – it’s a fun groomsmen proposal for inviting them to your big day!

9. For The Foodie Friends – Have An Amazing Barbecue Together

You know what they say: good food, good mood! Get your boys together for a potluck night of ribs, drinks, and reminiscing about your best times together. 

Everyone can bring a specialty dish that will show off their culinary skills, or you can cook together to bond and have a little friendly competition. After everyone’s done digging into their dessert, you can take out that fancy bottle you’ve been saving, give everyone a shot, and ask them to be your groomsmen. 

Bonus points if you dress it up with a personalized label to commemorate the occasion! Drinking your post-barbecue shots together will seal their acceptance to be part of your wedding party. It’s a lowkey but personal and meaningful groomsmen proposal idea.

8. For The Card Sharks – Hold A Fun Poker Night

You may be getting married to a lovely lady, but the woman you’ll want by your side for this one is Lady Luck! If your potential groomsmen get a thrill from playing a hand or two, host a poker night. Get some delicious snacks and settle down for an evening of bluffing, calling bets, and dealing cards.

When the games start winding down, take the opportunity to make your groomsmen proposal. Give your friends a set of playing cards, with groomsmen proposal cards inserted into each box. Write a special message on each proposal card saying why you want them to be your groomsmen. It’s a unique gift that’ll make your poker party a night to remember!

7. For The Jetsetters – Custom Traveling Kits

Now here’s one of the best groomsmen proposal ideas for destination weddings! Order customized leather travel kits for each friend you’ll ask to be your groomsman and best man. They’re a convenient and useful way for your groomsmen to stash all the essentials while traveling.

Each traveling kit can be customized with two initials or the three-initial monogram of your groomsman or best man. It’s a sleek, practical kit that will help them get ready on the go – there’s no better proposal gift than this if you’re asking them to travel for your wedding!

6. For The Practical Pack – Cooler Bags

If you’re stumped over proposal gift ideas for your groom gang, send them a practical groomsmen proposal gift: a cooler bag. Who doesn’t need a portable fridge for summer days and long weekends away? 

This one is the ideal size for your groomsmen to carry a dozen bottles of their favorite brews. It can stash snacks, cold bottles, ice packs – the possibilities for this bad boy are endless. Get these bags personalized with their initials and their favorite colors. It’s the perfect gift to take to backyard barbecues, tailgating, or the beach!

5. For The Boy Scouts Who Are Always Prepared – A Personal Dopp Kit

Here’s a great gift idea that has all the manly essentials: a custom Dopp kit with a personalized flask, shot glass, and carbon knife! Get them in their favorite colors or pick a specific hue to match your wedding day theme. The glass is a must for those late-night bachelor party shots, while that flask will help you and your friends drink the night away before your big day.

It’s definitely worth it to go the extra mile and get the full set with the carbon knife. After all, it’s a handy tool that every man should carry with him. Why not turn this essential into personalized groomsmen gifts that your buddies will appreciate? Your groomsmen will appreciate these gift sets long after your wedding day!

4. For The Men About Town – Bow Ties And Pocket Squares

No formal ensemble is complete without a tie and pocket square. Give your groomsmen these must-have accessories that are perfect for warm weather. These plaid picks come in a variety of colors that will suit their outfits for your wedding day, and it’s a versatile set they can use for other occasions!

Add a note to this bow tie set when you make your groomsmen proposal to your friends, telling them how much their support would mean to you. Whether it’s a day at the office or a night out, this bow tie set is a groomsman gift that your friends will cherish for years to come.

3. For The Dapper Dressers – A Custom Accessory Gift Box

Now, this is a groomsmen proposal box that’s practical and stylish! This classy gift set comes in a personalized wooden box for each friend you’ll be inviting to your wedding party. Each of these groomsmen proposal gifts has a personalized tie clip, money clip, and cufflinks that will add panache to their wedding attire.

Keep it simple by adding their initials, or make it a commemorative accessory by adding the date of your wedding day. Then, write a note letting them know how much it would mean to have them by your side. It’s the perfect groomsmen gift for the well-dressed set!

2. For Friends Who Live Far Away – A Celebrity Cameo

If you and your friends don’t live near each other, you can still make a groomsmen proposal that will make their day: a special invitation from a celebrity! See if any of their favorite TV or movie stars are on the app. For a certain fee, you can get a celeb of your choice to tell your groomsmen your own personal message…asking them to join you at your wedding, of course!

1. For The Smooth Gentlemen – A VIP Groomsmen Proposal Box

This is one of the best groomsmen proposal boxes to invite friends to your special day. This gift comes with an aluminum minimalist wallet, a pocket knife, a flask, and a bottle opener. All five of these items can be personalized with their names and initials. The gift box will also be customized with each recipient’s wedding title, like best man or groomsmen.

Are you making a big deal out of asking them with this gift? Yes, but it’s your wedding – no harm in splashing out! There’s no doubt that this groomsmen proposal gift will have them all saying “I Do”!

Make Your Groomsmen Bro-posal One For The Books

Your wedding party won’t be complete without your friends beside you, so make a groomsmen proposal that they won’t be able to resist! Give these creative gifts or try these cool activities to invite your prospective groomsmen. At least one of these fun proposal ideas will be perfect for your friend group!

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