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How to Pick a Best Man So You Don’t Regret It

Ok, groom. We have a question for you. You don’t have to say the answer out loud, just kind of… admit it to yourself. Did you know who your best man was going to be before you even proposed? Well, we know it might be too late, but we’d like you to hold your horses for just a sec. Until you get to the end of this article, at least. If you haven’t asked anyone to be your best man yet, you have the luxury of actually thinking about it. Here’s how to pick a best man.

Oh, and one more thing. After you go through this list, you may discover the only person who actually meets all the requirements is, like, your dad. Who is already going to be at the wedding, after all. It’s ok; as long as your best man fits some of the points below, you’ll be alright. We’re crossing our fingers. Let’s go now and pick a best man. 

pick a best man

Photo from Nickola & Gary’s real wedding by Zi Fernandes Photography

At the very least, you should be able to count on your best man for these two things: a sympathetic ear and a helping hand. Does he possess these two traits? Because, you’re going to need them.

Before the wedding, you’ll be frustrated with the planning, and you’ll definitely argue with your other half about money at some point. The road to ‘I do’ isn’t all sunshine and lollipops. Is your best man a good listener? Can you tell him practically anything, and he won’t judge? If not, then maybe he’s not the best candidate.

As for the helping hand – you’re going to need a bit of that too! Many best men assume their only job is to organise a stag do, and to avoid drinking too early on the wedding day, so they can stand at the altar without swaying like they’re on a boat. There’s more to it than that. Is the best man the type of guy who gets stuff done? If he’s always been there when you needed help (like with moving), and when he promised something he actually did it, then you got a good one. But if his only help ever has been buying you more drinks when you’re already sozzled, then any practical stuff may be beyond him. Your call.

Is the best man dependable? Dependable is a big deal in weddings (in life too, of course). Dependability means he’ll show up when he says he will, he’ll do what he promised, he won’t forget the rings, and when you’re on your honeymoon, he’ll return the suits on time so you don’t get charged a late penalty. If he’s the opposite type, you may have problems. Don’t pick a best man who barely shows up to work on time every day.

pick a best man

Photo from Sarah & Tony’s real wedding by Liam Kidney Photography

He needs to look out for you. When you go out drinking and you reach the point of no return, what does the best man do? Does he take you home, or at least call a taxi? Or does he leave you propped up next to the pub bins and goes home himself? You wake up the next day, and you don’t know how and why you’re there. Where has your mate gone? Don’t pick this guy for a best man. If you go on a stag do in a foreign land, he’ll leave you next to some bins over there too. And we all know how those stories end. You’ll have no wallet, no phone, and your hotel may be at the other end of the country. And you don’t speak the language. 

This leads us nicely into embarrassment. Does your best man love embarrassing you? Or even worse… terrifying you? Would he find one of those stag kidnapping pranks hilarious? Or, make you jump into a body of water that looks like a lake but is actually a puddle? Or, tie you to a lamp post without a stitch on? We could go on, but we’re basically describing an immature 11-year-old prankster here. Is that your best man’s secret identity? Avoid asking him to be your best man at all costs.

Making a speech is a traditionally assumed role for the best man. True, things have really changed now, and it’s no big deal if the best man doesn’t do one. But let’s say you want to stick to tradition and have the best man speech. Is your best man painfully shy? Has he never given a speech before? Does he go all pale and sweaty just at the thought of it? Depending on how much that matters to you (and how good he is at all other aspects of being the best man) you can tell him he doesn’t have to do it. But if you really want to have the speech… then pick a best man who’s not afraid of public speaking.

pick-a-best-man

Photo from Allida & Evan’s real wedding by DKPHOTO

And now, we feel you’re ready for the big question. Does your potential best man disapprove of your other half? Maybe he’s never said it straight up, but you kinda get that impression from the way he talks about her. Even if he’s being subtle about it, it’s always there, niggling and lingering… Not good. Not good at all. A good best man is a gentleman – he keeps his opinions to himself. But if you happen to have a best man who stands behind this marriage thing 100% and thinks the bride is truly the best woman for you, then he’s a keeper. Don’t pick a best man who hates your fiancé.

In conclusion… you need an upstanding member of the male population to be your best man. The kind of man you’d like your sister to date. The clue is in the name really: BEST MAN. If you don’t know anyone who meets at least a few of the requirements, then you could get creative. Get a best woman. Or two best men – ideally, they’ll have all the above qualities between them. Ask your dad to be your best man! Or don’t get a best man at all – it’s not a law that you should have one. Nobody wants to tell a story entitled ‘how my best man ruined my wedding’.

Main photo from Laura & Patrick’s real wedding by Deirdre Langan Photography

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Rachel Green

Rachel Green

If you think the bride should always have the last word, then Rachel is on your side! A devoted fan of everything quirky, unusual, colourful or crafty, she loves scouting WOL's real weddings for unique and fun touches. When not gazing at pictures, she's dispensing no-nonsense advice on everything from reception entrance songs to bridesmaid problems.

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