I’ll be honest—I didn’t think choosing my groomsmen would be so hard. I figured, hey, just round up the bros, right? But then came the questions.
“If I pick this Ash, I have to pick that Perrie, right?”
“What if one of them can’t make it?”
“What if one of them shouldn’t make it?”
“Is it okay if my brother isn’t my best man?”
And my personal favourite:
“Do I even have enough close male friends who own a suit?”
If you’re getting married, you’re probably already juggling the ROM date, the guest list [37. Who to Invite to My Wedding?], and the age-old debate of whether to serve or not serve shark’s fin.
So let me help you out here—man to man—with a few thoughts on how to choose your groomsmen without turning your wedding into a diplomatic summit.
1. Pick People Who’ve Been There, Not Just People Who’ve Been Around
Start by asking: Who’s been there for me?
Not just during the fun nights at CQ, but the tough seasons too—when the relationship nearly broke, when you lost that job, when you accidentally called your fiancée by your ex’s name (and somehow survived it).
Groomsmen should be your inner circle. Not your loudest drinking buddies or the guys you haven’t properly spoken to since NS, but the ones who actually know you.
This is a big moment. You want people next to you who will celebrate it with heart, not just show up for the photo ops.
2. Quality Over Quantity
There’s no rule in Singapore that says you must have 6 groomsmen just because your fiancée has 6 bridesmaids. We’re not arranging national day parade contingents here.
Have 2, 4, or even 1. What matters is that they matter.
At my own wedding, I had three groomsmen. My best friend from JC, my younger brother, and a church mate who’s seen me at my lowest. That was enough. (Plus, fewer suits to coordinate.)
3. Consider the “Wedding Day Reliability” Factor
Here’s a truth you won’t find on Pinterest: Some people just aren’t meant to be in the wedding party.
If he’s always late for brunch, frequently ghosts your WhatsApp group, or once got lost on the way to his own birthday dinner… he might not be the best person to hand the wedding bands to.
Choose groomsmen who are dependable—especially because wedding days run like precision clockwork. One delay, and suddenly your solemniser is double booked.
4. It’s Okay to Mix It Up
Your groomsmen don’t all need to be childhood friends. It’s okay if one’s your colleague, another’s your cousin, and one’s your regular gym bro.
What binds them together isn’t their shared history—it’s you. You’re the common thread. And if you trust them, they’ll respect the role.
5. Be Honest With Yourself (And Them)
If someone expects to be a groomsman but you don’t feel comfortable including them, have the courage to be honest. That conversation may be awkward—but trust me, it’s better than forcing it and regretting it later.
Explain it with grace. Maybe you’re keeping the group small. Maybe you want them to enjoy the day without responsibilities [30. What Are the Responsibilities of Groomsmen]. (There’s always usher duty, right?)
6. Don’t Forget to Say Thank You
Being a groomsman isn’t just standing beside you and looking good in a bowtie. It’s showing up for fittings, helping with logistics, calming you down when the caterer says they’re “on the way but stuck in a jam.”
So appreciate them. Write a card. Buy them a solid gift—local ideas include customised cufflinks, a bottle of whiskey from Brass Lion, or even a cold brew set from Parallel Coffee Roasters if they’re coffee guys.
Final Thoughts
Choosing your groomsmen is a small part of wedding planning, but it sets the tone for the day. These are the men who’ll walk with you, literally and figuratively, as you take that next big step.
So pick with intention. Pick with heart. Not for the gram, not for balance with the bridesmaids, but for you.
Because at the end of the day, when you’re standing up there, hands slightly sweaty, nerves all over the place…
You’ll want to look to your left and see the ones who’ve always had your back.
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