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Best Man

22 Cool Ways to Ask Your Best Man


Ok, you’ve done the easy bit and asked your girlfriend to marry you. Now things get really tricky.

Just how do you ask your best mate to be your best man?

Going down on one knee? Too formal. Hire a flashmob? Too much. On his favourite beach? Too weird. Plus, you don’t want your bride-to-be to feel overshadowed (despite the fact you took her to see the latest Star Wars movie, treated her to a McMeal and then took her to the exact spot where you ordered your first takeaway together as boyfriend and girlfriend).

So, here are some fun, blokey ways to pop perhaps the second biggest question you’ll ever ask… “Will you be my best man?”

Bow Tie – Mrs Bow Tie

Smart, stylish and a great way of giving him a taste of things to come before you pop the question:

“Will you be my best man, and do you promise to wear this and look smart for once?”

Enjoy first-class service and a fantastic range of designs from Mrs Bow Tie.

Check them out here!

Bow Tie Mrs Bow Tie

Socks – Super Socks

There are just so many reasons we love Super Socks, and being a great way to propose to your best man is one of them. Either spell it out with words for him or get him a pair of ‘face mash’ socks. It’s the perfect way to celebrate your bromance.

Check them out here!

Socks - Super Socks

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Whisky Glass – keepitpersonal.co.uk

After all the times he’s left you with an empty glass (the round-shy, barman-dodging, cheapskate!), presenting him with an empty glass might be quite fitting, especially if he’s a whisky fan. With Keep It Personal, you can create your own message or they have a huge selection of best man products to choose from.

Check them out here!

Whisky Glass - keepitpersonal

Personalised Glengoyne Whisky – Glengoyne

No one wants to see an empty glass, so fill it courtesy of our favourite distillery, Glengoyne. Not only can you present your BMF with something personal, but it’ll also be filled with one of the smoothest, richest whiskies he’ll ever have the pleasure of tasting.

Buy yours here!

Personalised GlenGoyne Whisky - Glengoyne

Whisky Miniature – Real Unique

Don’t actually want to buy him a whole bottle? Fair enough! Go miniature with a personalised Jack Daniel’s bottle that has a handy Yes/No answer label. It’s also small enough that you can share one each before heading into the ceremony on the day. A neat little idea from Real Unique.

Check them out here!

Whisky Miniature - Real Unique

Cufflinks – Etsy

Cufflinks are cool – it’s as simple as that. But these wooden bad boys from Etsy are a cut above. Literally, as it happens, as they’re engraved in wood and make a fantastic memento of the day, plus, they’ll stop his sleeves flapping about while he’s comedically ripping you to pieces during his speech.

Get yours here!

wedding party cufflinks etsy

Guitar Plectrum – Printed Guitar Picks

Thanks to Printed Guitar Picks, asking your best man to be your best man is the new rock ‘n’ roll. A great way to get him to say “I do” and give him a cool piece of rock memorabilia. You can create your own design, get a photo printed or keep it simple with a message… then get the band back together, man!

Get yours here!

Guitar Plectrum - Printed Guitar Picks

Sunglasses – Bridea

Why just stop at the best man? Thanks to Bridea, you can get the whole of Team Groom kitted up with best man, groom, usher, groomsman, whatever shades. Great for a wedding day photoshoot with a twist, plus you can personalise each one with the wedding role and colour!

Get yours here!

Sunglasses - Bridea

Scratch Card – Real Unique

“Be lucky!” This is a fun and different way to ask him, and it’s especially handy if he doesn’t live close by (or is simply not allowed out to play very often having tied the knot himself). Real Unique have some funky designs and other useful gift ideas for the rest of your groomsmen.

Check them out here!

Scratch Card - Real Unique

Hip Flask – keepitpersonal.co.uk

If he’s the kind of guy who enjoys a tipple, or you just want to make sure he’ll have Dutch courage for you both to share on the day, then a flask is not only really handy, but it also looks hip (see what we did there?). Pick a cool design or use words of your own – just make sure he keeps it handy and full on the day.

Check them out here!

Hip Flask - keepitpersonal.co.uk

Golf Balls – Golf Online

Rather than balls up your attempt to ask your best man to help get you through the biggest day of your life, hit the sweet spot with a personalised golf ball. While out playing, you can keep the ball hidden and switch it with his at the right moment to surprise him. Then watch the Slice King hunting in the rough for hours to recover his new, special ball.

Check them out here!

Golf Online

Football Shirt – Direct Soccer

Celebrate your bond of love, laughs and football with a personalised football shirt. Add a number, name or message to ask him to be your wedding strike partner. Sure, he can’t actually shoot for toffee, but at least he’ll look a complete player in a smart shirt from Direct Soccer.

Check them out here!

Football Shirt - Direct Soccer

T-Shirt – T-Shirt Studio

Ask the big question and free him from his own terrible dress sense by designing him something cool and personal with the T-Shirt Studio. Really user friendly, you can upload photos or artwork, or add your own words or message – just make sure he knows he has to dress smartly on the big day.

Check them out here!

T-Shirt - T-Shirt Studio

Card – Norma & Dorothy

Now, you could grab your crayons and make your own ‘Will you be my best man?’ card, or you could get this funky number from the arty geniuses at Norma & Dorothy. Retro, cool, classy and plenty of room for your own personal message inside. Just remember to be nice, he’ll already be planning your best man speech, after all.

Card - Norma Dorothy

Personalised Spirits – Prestige Drinks

If you want to up the stakes and add a touch more class to your question, then Prestige Drinks have a very full drinks cabinet packed with top quality beverages that you can add a message to. They even have the glass bottle etched to create something truly unique that any man would love.

Personalised Spirits - Prestige Drinks

Beer – gettingpersonal.co.uk

What could be better for your best man than picking up an ice-cold bottle of beer with his own face on it? How about a bottle of beer with your face on it?! You can choose either as a brilliant way to tell him your news and ask him to be your best man.

Check them out here!

Beer - gettingpersonal.co.uk

Chocolate – Morse Toad

What’s not to love about this sleek way of asking your friend/brother/close personal acquaintance to stand by your side on your big day? It’s really easy to add your own message and a photo, then you can let his inner chocoholic take hold as he agrees to be your best man.

Morse Toad - Choc

Beer Bottle Label

Get ‘Team Groom’ together and treat all your groomsmen to a beer with their own personalised labels. A nice way to surprise them all with the good news and ask them to be with you on the big day. Create your own design or do a spoof of your favourite brew. Not only is it a bit different, but it also involves beer. Win/win!

Beer Bottle Label - PersonalisedBottleLabels.co.uk


Friendship is like fine wine: it only gets better with age. You can celebrate the fact that not only has your friendship lasted over the years, but that he’s now the one guy you want beside you as you take your biggest step yet. Personalised Wine Store a load of fantastic ways to say thanks and give him a great keepsake.

Personalised Wine Store

Wooden Box – Whatnot Wood Craft

Create your own message of thanks with a stylish wooden box your best man can keep his treasured possessions in (like the money he hangs onto when dodging his rounds). Make it personal by adding your own message to a simple but classy design, like: “Stop dodging your rounds!”. Wooden, manly, smart.

Wooden Box - Whatnot Wood Craft

Balloon – Etsy

Quirky, different, plus he’ll have something to play with when you go to see him (you know how his mind tends to wander if he’s not kept occupied). This POP ME best man balloon is great for your own groomsmen reveal party – OK, it’s not a thing, but it could be! Start the trend!

personalised pop balloon etsy

Mug – Not Another Bunch of Flowers

Proper mug, you mug, mugged off… there’s no end to the fitting tributes you can pay your best mate via his own best man mug. Super speedy delivery if you need it in a hurry and a great range of different gift ideas you can tailor to suit your needs for this most manly occasion.

Check them out here!

Not Another Bunch Of Flowers

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