The first thing to remember about proposing a toast is that it is really a short speech, and the three criteria for a successful speech of any length are: you’ve earned the right to give it, you feel strongly about the subject, and you want to do it. In almost every toasting situation the criteria are met, otherwise you likely wouldn’t have been asked to participate.
You will have earned the right to propose the toast by virtue of your association with the person being toasted. You will have some emotional investment in the event through your presence at it, which combined with your feelings for the person being honoured means you will meet the criterion of feeling strongly about it. Finally, if there’s any doubt about you wanting to do it, just remind yourself of what an honour it is to be asked. On the other hand, if you don’t really know the person very well and have no strong feelings about the event, even if you’re an accomplished speaker you should decline the request. Everyone, and especially the guest of honour, would know you’re just playing a role, and your participation will in no way enhance the event or your reputation; in fact, it’s apt to diminish both.
Toasts should be short and to the point with everything you say being both relevant and interesting. Keeping a toast short, relevant and interesting will avoid the most common mistake people make when proposing a toast, which is turning it into a speech about themselves. The audience wants to hear about the person being toasted, not about you, although it’s appropriate to include information establishing the relationship between you and the person being toasted, provided, as already mentioned, it’s both relevant and interesting. For example, when toasting a bride it might be relevant that you met her through playing bridge with her parents, but it’s not very interesting. Remarks about her school term abroad in Scotland might be interesting, but hardly relevant unless it had something to do with how she met the groom.
Whether you intend to speak “off the cuff,” use notes, or speak from a marked-up script, as in every speaking situation it’s important to initially write out your remarks in full. Writing out your remarks allows you to effectively organize, edit, time and rehearse your material. Even a very short toast should be rehearsed, if for no other reason than to identify and avoid cumbersome phrasing or words you might have difficulty pronouncing.
Never tell a joke when proposing a toast! There is no toasting situation in which a joke is appropriate. However, it is perfectly in order to relate an amusing anecdote involving the person being toasted, particularly if it’s relevant to establishing your personal relationship.
Most important of all, don’t look at the person you’re toasting until the very end of your toast. Instead, make eye contact with all parts of the audience until you ask them to rise and join you in the toast. Then raise your glass, pause, turn to the person being toasted and emphatically and clearly conclude your remarks with “To (the toastee)!”