Sing to groom at reception

A college friend once learned a whole song for mutual college friends, and then sang at their wedding.

We all swooned. It was amazing!

If you are comfortable doing it, DO IT.

I have seen (heard?) this done at a few weddings and quite honestly, unless you’re a trained professional singer, it’s never a good idea. Emotion, nerves, having a crowd staring at you - they’ll all play a part and chances are your performance will not be what you’d like it to be, which can be awkward and embarrassing. And if you’re shy, it’ll be worse. However! I do have an alternative suggestion for you: why not record a song? That way you can take the time to get it really right and not have all those other factors play into it, meaning you can perform absolutely at your best and get a much better easily.

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Very different to perform at someone else’s wedding compared with your own, though!

The last wedding I went to, the bride sang a song that she was going to walk down the aisle to. The DJ had it prerecorded so he Just played it back before she started walking. That way there’s no mishaps, wrong lyrics, freight. That sort of thing

I think its very romantic

Not sure if you are planning to do a first look, but you could always sing to him privately with just you two! That's if your main concern is singing in front of people, but I know you mentioned that he wanted others to hear your voice.

If you aren't sure about singing in front of guests, then the private serenade idea would be super sweet and romantic, kind of like your wedding gift to him!

I think it will be beautiful and everyone there will love it! ESPECIALLY HIM! And what better way than to start off by doing that for him?!

Any chance you’re having an after party ?
When I think back to my wedding, squeezing this in would’ve felt awkward and forced....but our casual post wedding hang at the bar while everyone’s feeling loosened up and silly , it would’ve been perfect.

It’s nice that you want to do this sweet thing for him, but you mention being shy and the “stage” at the wedding is pretty intimidating so I worry how that would turn out...and once you start there’s no backing out if you change your mind and suddenly feel too awkward. Also an odd point, but remember your wedding will be one of the most photographed/recorded moments of your life, so I can guarantee it will be filmed — so that’s food for thought !
Another thought on the shy scope is if you’ll feel nervous and anxious about it — you really want to set yourself up to enjoy your wedding day as much as you possibly can, and it will be a blur anyway. If gearing up to sing would preoccupy you at all, I’d skip — just not the kind of energy I want on my day at all.
Just some things to think about !

I would find that very awkward, but it's your day - you should do what feels right.

I have seen people do that.

maybe you can record yourself and give it to him as a gift for him to listen to

I would also say it's awkward... just my opinion though.

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I second this idea. Or record yourself singing and play it for your first dance. However, I am not a fan of the singing to him at the reception idea.