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Will You Be My Best Man? How To Ask

Picking out your wedding party is one of the most exciting parts of getting married. You’ve probably been dreaming about asking your closest loved ones to be a part of your big day for a long time, and the best man proposal is the biggest ask (other than the bride, of course)!

Plus, your besties are going to make things like your bachelor party and other events extra fun.

However, asking your best friend or brother to be your best man might seem a bit intimidating or uncomfortable. It’s an important role, and you want them to say yes! While some do it really low key, others go all out to ask their best bro to upgrade to best man. Keep reading for some great ideas for the best man proposal.

What If I Don’t Want to Do a Proposal?

funny best man

For some people, doing a best man proposal is just weird! You may feel that your relationship with your best man is not close enough to do something like that, or you may just want to have done only one proposal in your life. There are lots of reasons why one might just shoot a quick text to ask if they feel up to it.

That being said, if it’s not your thing, you don’t have to do a best man proposal! This is a totally optional thing, and your wedding is ultimately yours. So no pressure to go through with it if you’re not feeling it!


6 Ideas To Ask Your Best Man

If you’re sold on the idea of a best man proposal, there are tons of cool ways to do it! One way to do so is through a nice gift, either for your best man or for all your groomsmen. You can read here for a full list of groomsmen gifts, letting your boys know you’re ready for them to suit up.

If doing it through a gift is not your thing, then that’s okay! There are tons of heartfelt ways to let your best man know that you want him by your side on the most important day of your life. Below, we list great best man proposal ideas.


Asking Over Food and Drink

One of the best ways to ask your buddy to be the best man is to write the big question inside the box of a pizza! Bring it over to his house for some video games and a drink and let him know you want him to be the best man when he goes for a slice!

You could also do a similar thing by packaging a bottle of liquor or a pack of beer with a note then asks the question. That way, you guys can share a cold one together after the big reveal! This will be a comfortable and fun way to ask your best friend to help you out.


Writing Him a Note

If you want to do it in a nice and meaningful way, you can write a sweet note asking your best man to take on the role. This one has a very cute design and comes with an envelope that you can hand to him and watch his face when he hears the big news.

Writing him a note also goes nicely with giving a gift or a bottle of alcohol! It’s a very warm way to let your best man know that you care and want this to be a memorable experience.


Compiling Old Memories

One of the best ways to ask such an important question is to walk down memory lane and remind your best man why he’s the one you’re picking for the big day. By picking an old photo to spread the love, whether it be from elementary school or college, you can acknowledge how important this relationship is for you!

This example offers one old photo but you could do something like a collage to own the entire history!


Prank Ask

Though this is more of a best man pranking groom than the other way around, you could do something similar to surprise your best man and ask him for the big day! Dressing up in a silly costume like this will surely get the message across.

You could also do something slightly less silly, like getting a puzzle made to ask, so he has to sit and do the whole thing before hearing the big question. Or, you could do a prank call, something a bit confusing to get him to surely say yes!


Ask with Your Fiancee

If your best man is also close with your new wife, you could ask as a group! A silly ask like these boxers (or maybe just t-shirts) is a fun way to get everyone into the fold! This is a great way to acknowledge that your best man is not only your best friend, but that he matters to both of you!

It’s also a good way if you would like your fiancee and your best man to grow closer! This is a good memory to start the long line of shared experiences over the wedding process for them to gain a stronger relationship.


Asking Your Boys As a Group

If you can’t pick a single best man and want to ask all of your friends to be groomsmen at once, you could use any of these ideas to ask them as a group! For example, you can get a few large pizzas to ask your friends that big question, or could hand out several cards.

It’s also a great excuse to get all of your friends together, even if they don’t know each other that well, because as groomsmen, they will have to work together and act as good friends to help you enjoy your wedding. Asking as a group is a great idea!


More About Groomsmen

Here at Yeah Weddings, we’re here to help with all of your wedding needs. From bachelor party hashtags for the groomsmen to the differences between a tux and a suit, keep reading for all of your wedding party needs.

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Katie Sheets

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