Groomsman Proposal 101 - How to Ask Your Groomsman to Be in Your Wedding

So you got the hard part out of the way, and your (now) fiancée has the ring and has accepted your bid to be married. Now is the easy part: asking your buddies to be groomsmen in your wedding! Well, it’s not so easy once it gets down to it. For some guys, this may be really easy, but for some it may be really hard. We’re going to answer the question today for both types and anyone in the middle. “How do I ask my groomsman to be in my wedding?”

Let’s talk about it! We are your source for all things grooms & groomsmen, so let’s dig right into it!

How Many Groomsmen Should You Choose?

Firstly, let’s take a look at how many groomsmen you plan to add to your wedding. We do want to throw out a disclaimer, when we use the term groomsmen, this could also apply to groomspeople, or anyone in your wedding on the “Groom’s side.” 

There’s certainly not a “limit” to how many groomsmen you choose for your wedding; this is something you’ll want to discuss with your future wife, as the number will probably be dependent on how many bridesmaids she plans to have. Every wedding is different, but be sure to include anyone who truly matters to you and your future. 

When is the Best Time to Propose to Your Groomsmen?

Some people plan their wedding years in advance, some plan it months, shoot some plan it hours beforehand. (City Hall wedding, anyone?) Men have a slightly different type of friendship than women, and for the most part, can plan on nothing falling through with their buddies between now and next November. This isn’t to say drama can’t occur, though, so you won’t want to rush it right away and overcommit too early. You can wait a few weeks after you propose to your wife to start your list. 

Ideally, you’ll want to give the groomsmen time to be prepared for the wedding, emotionally and financially. Somewhere around 9 months to a year ahead is pretty healthy, and 6 months should be enough time. This way, they can make arrangements and plan for your big day.

Check Out our Blog on What Makes a Good Groomsman

How to Ask

How you ask will depend on the method by which you choose to ask. It’s also going to depend on the relationship you have with your buddies. Ultimately, you just want to be REAL. You want to be genuine, and you want them to understand the reason WHY you are asking them. If you can handle that, then it won’t matter what way you ask. So be honest, real, and genuine, and remember to explain to them what qualities they possess that have kept them important to you over the length of your friendship. That’s all there is to it. 

Here are a few fun ideas to help get you thinking about you you might go about it.

5 Ways You Can “Propose” to Your Groomsmen

Plan a Night with the Boys

The first method we’ll go over is the team invite. This is where you plan a night out or in with the boys and just meet up to hang out. Some guys get together often, whereas this could be more challenging if you’re older or you don’t all live in the same place. This can be a great way to bro out and get together and get something checked off the list all at once. 

If you’re a natural-born leader and not afraid to huddle the men up and give a speech, this might be your route. You can introduce each guy and ask them all in front of you as if you were the QB or leader of a troop entering battle together. 

Personal Call / FaceTime / Zoom

This method can be the simplest, but not necessarily easy. Some guys have really close connections, and it’s not weird to talk on the phone. Other guys may find it weird to just hop on the phone and call, but for something like this, it’s important to note how special the person is to you and why you’re choosing to have them on your wedding squad. 

The privacy of a call means you can open up and be honest, and talk openly about any concerns or other things you may want to talk about privately. (Which you may need to meet individually with the guys later anyway) 

Personalized Groomsman Proposal Gift

Regardless of HOW you ask, the Groomsman Proposal has become a normal occasion to provide some sort of gift. It doesn’t need to be something huge, just something to show a bit of gratitude for their time and energy for the wedding. It has become a custom amongst guys to grab something between say $25-$100 (normal guys, not talking about rich guys here) just to say thanks and LFG. 

A personalized groomsmen proposal gift gets the job done by adding a token of appreciation to your words, and you don’t need to break the bank to show the person they matter.

Video Groomsman Proposal

If you are a little less personal but more of someone who can make video content, then this could be a good way to send your proposals out. A basic text message may be a bit too informal, but if you were to drop a personalized video message for each individual groomsman, that could be an interesting way to spread the word. This could be a fun way for you to make it creative and fun, while also getting the job done. 

Videos offer the opportunity to be funny, cool, chill, inspirational, motivating, or whatever effect you want to have on your buddy.

Handwritten Groomsman Proposal

Some things are easier said than done, and having a heartfelt heart-to-heart isn’t always easy to have with a male friend. If you want to say some things that you don’t exactly feel comfortable saying out loud, then this could be an easier way to make sure you get your point across. Guys can be a bit difficult to have serious conversations, often creating a sense of humor when faced with too much emotion, and if you’re surrounded by the other guys, you may not get a chance to say how you really feel without a good joke grenate getting tossed in to blow everything up.

A handwritten message can also be accomplished alongside a nice personalized gift, for example. Now, where can you find something like this?

Well, here at Stag Pack, you know you can find affordable groomsmen gifts that include personalized items, as well as a personalized notecard that you can either have printed or write by hand. We offer groomsmen gift packs for any type of dude, from the Golfer to the Outdoorsman, to the Executive & more!!! Good luck to all the Grooms out there, and if you have a fun way of proposing to your groomsmen that we don’t have here, please let us know, and we might feature you on our social media!