A few years ago, I lent a large amount of money to a friend to help him out at a tough time. We now live in different cities, and, although I’d say we were still friends, we aren’t as close as we were — mostly due to the distance, I think. There was no contract involved. 
I trusted my friend then and 
I still trust him now. We don’t speak regularly, but when we do, he doesn’t mention paying me back.

I don’t know what my friend’s financial situation is now, a few years on. I want to bring up the subject with him of repaying the money, but I don’t want to put 
a huge deal of pressure on him. I’m conflicted!

As you’ve discovered, lending money to a friend can be problematic. Of course, he should, as your friend, have paid it back without needing to be asked. But the tricky situation you’re in is all too common. It’s highly unlikely he’s forgotten the loan. He either doesn’t want to, or can’t pay it back.

Either way, he is taking advantage of your silence, hoping that you have forgotten or written it off. Maybe he thinks you don’t need the money. You say you’re not as close as you were.

Do you not think this distance, rather than being merely geographical, is at least partly caused by an unspoken tension between you over this money? Perhaps he hasn’t been contacting you because he’s dreading an awkward conversation. And it sounds like you don’t want to contact him because you’re scared he’ll feel pressurised.

But if you don’t talk, you’ll never get your money back, and you’ll also lose your friendship for good.

In an ideal world, you’d have agreed terms at the start, rather than relying on trust. Now, you can only try to rescue the situation. Think about what you want and how you’ll feel if he says he can’t pay you back or, worst-case scenario, denies any knowledge of the money or says he thought it was a gift. Could you afford to write it off? Could you still be friends? Would you sue him?

If he is willing to pay it back, but not in a position to give you a lump sum, you could set up a payment plan for him.

Whatever you decide, you need to communicate with him, or this will continue to hang over you .

My girlfriend and I are planning our wedding. We’re excited to be the first ones in either family to have a same-sex ceremony. The only problem is my teenage son. He lives with his father, and is uncomfortable with the fact that I’ve come out as a lesbian. He’s begged me not to get married, because he feels that it’ll embarrass him in front of his mates. I won’t change my plans — but how can I persuade him to accept us, and play the active role in our ceremony that I would like?

Congratulations on your forthcoming wedding! Of course you’re happy and excited and in love, but perhaps your elation is clouding your ability to empathise with your son.

Please put your own feelings to one side for a moment, and instead think about his. He’s a teenage boy, with all that entails. He’s already dealt with the break-up of your marriage to his dad, the revelation that you are a lesbian and that your relationship with his father was not as it seemed, the arrival of a new step-parent figure… and now you are expecting him to play an active role in your wedding, which he is already feeling embarrassed and conflicted about.

Give him some slack. This is tough for him and he must be dealing with so very many contradictory emotions, probably some that he can’t even articulate.

You can’t persuade him to accept your relationship. This is about emotion, not argument. He is worried about his friends because he’s at an age where their opinion is the most important.

You say you won’t change your plans, and nor should you, but asking him to play an active role in your nuptials is perhaps an expectation too far.

Maybe you need to compromise and accept that just having him there will be enough. Talk to him and listen to what he says. If you pressurise him, or try to make him feel guilty about this, you might end up not only not having him at your wedding, but in your life at all. The fact he lives with his father shows that there is already distance between you. Don’t make it bigger.

Contact Hilary via email at agony@thejc.com, anonymously or not. Or write to her at 28 St Albans Lane, London NW11 7QF