‘I am best man at my friend’s wedding but he is making a mistake’

My best friend has been going out with a girl for the past few years and I don't like her. None of our friends like her. He doesn't know this and he is going to propose to her. They are moving to a different part of the country and he will have no life and I don't know how to say it to him.

She's really rude to us all, kind of stand-offish, but I don't think he sees it. I don't want him to move away or to be miserable for the rest of his life if he marries her.

He has asked me to be the best man and my gut reaction was to say no – I don’t know how I could make a speech congratulating them and saying that it would be the beginning of the best part of his life. But I don’t want to let him down either as he has never been that lucky with girls and I don’t want to make him feel bad.

What should I do? I've said yes to the best-man job but feel totally fake with him and sad because I think this could be the end of a really good friendship.

The question of whether to tell the blunt truth is always a big one. The relationship is the deciding factor in terms of how much the other person should hear from you and in this situation your friend has asked you to be best man so this is a very important relationship to him.

Of course he is completely free to choose who he wants to marry but it seems that you and other people close to him have grave doubts and these are unexpressed. Why have you not yet spoken? Is it that you fear he will take offence and stop being friends with you? It seems that a broken friendship is in the offing anyway as it sounds unlikely that you will be a constant visitor to his home in the country.

The first question to ask is not if he “wants” to hear your opinion on his relationship but whether he “needs” to hear it. If you can answer yes to the second question, then it up to you to gather the courage and speak honestly to your friend.

If you are doing this for your friend’s benefit and not because you are afraid of causing him hurt, then it would seem that your direction is clear. At the outset, you need to be clear that, no matter what the outcome is, you will always stand by your friend and be there for him if he ever needs you.

This means that you will not take offence if your friend is hurt and angry but will keep contact regardless. Perhaps the best way to do this is to set aside a private time to talk to your friend; ask him how he thinks his partner is getting on with his friends and if he can see any difficulties.

Perhaps ask if he would be open to hearing some comment from you on the relationship and express your concern about how this might affect the two of you. If he still wants to hear your comments at this point, then speak very clearly and openly.

However, if he chooses to ignore your advice, you will then need to adopt a different approach. Many people do not particularly like their friends’ partners but they know that in order to have the friend in their lives they have to find accommodation with the partner and engage with them in the best way possible.

This cannot be fake as the effect of “pretend liking” is negative for both parties. It is always possible to find a connection with someone even if it seems unnatural at first. Most of us find that if we spend enough time with another human being we can find a tolerance and even a friendship – think of schools, clubs and so on.

It may be that if your friend continues with his relationship, you will need to put aside your judgments and find something worthwhile in his future partner. The reason you would do this is because the friendship is very valuable to you and this makes it worth putting aside your judgment for the comfort of your friend.

The longer we wait to speak truthfully, the more murky the eventual engagement: think of telling a colleague they have body odour – the sooner you speak the less likely the other person is to worry about how long you have been hoarding the thought. So speak to your friend as soon as possible and do him the honour of treating him as an adult who can manage his own feelings.