Hi Babysafari. Is it a really diddy cup? If it isn't, I highly recommend going miniature to solve the issue of you having to hold it. I found a mini Babycup (really tiny open cup for babies and weaning) worked really well and it wasn't long for my lo's to use it without help/me holding it. Definitely worth trying that one and asking the nursery to use it too. Will he be having milk/cheese/yogurt in his meals?