Virginia Ironside's Dilemmas

Dear Virginia,

I'm in my late forties and I've met, on the internet, a lovely man of 30 who appears to be in love with me. I am certainly in love with him! We've been going out for six months. He has a good job but his parents have both died leaving him nothing, and I know he's desperate to buy a flat. He's always talking about how insecure he feels. I feel tempted to give him the money to put down on a flat. He's never asked for it, I should add. What do you think?

Yours sincerely, Freya

One of the commonest faults that we have is that we think we have the power to second-guess people. That's why, apparently, faced with a row of toilet cubicles, we usually choose the one next to the nearest, thinking that that is the one that must be one least used. I saw, again in a toilet, a woman drying her hands on the furthest part of a roller towel. She clearly thought, just as I did – and no doubt everyone else – that most people would choose the front of the towel to dry their hands on, so she'd use the back.

This behaviour, Freya, is just like yours, thinking that because this young man hasn't actually asked you for money, he must be genuine. You think you're second-guessing him. But I suspect that it's he who's second-guessing you. He knows that if he just moans about his living conditions for long enough, he doesn't have to mention money, because you will, at some point, consider giving him some. And then he'll be able to exclaim with delight, saying: "Oh, I never thought of that! How kind!" when all the time he's been plotting to get you to offer him money right from the start.

I hate to say it, but this man sounds like a con-artist. And a really good con-artist will never ask for money – he'll always just set the scene so that there's very little you can do except offer it. He'll never steal your favourite painting. He'll wait until he's driven you into a curious corner in which you just find yourself taking it off the wall and handing it to him.

It's clear you're not only flattered to find this man's in love with you, but also slightly amazed that someone so young should fall for someone of your age. Now I'm not saying he might not be perfectly genuine. But bear in mind that you met him on the internet – a fairly unconventional way to meet someone. You have no friends in common, no shared workspace, nothing. He could have picked you from a list of older suckers just as carefully as a paedophile picks a child to abuse.

If I were you, I'd keep your wallet firmly shut. If he ever does ask for money, you'll be certain he's a con-artist. If, after another year in which he still appears to be just as devoted as he is now, and during which you haven't given him a penny, you still feel you love and trust him, then by all means offer him perhaps the loan of a downpayment on a flat and see how he takes it. But wait. And wait a long time. You may think that the money you're thinking of giving him is worth it for the pleasure he gives you. But in the long run, you may well find yourself giving him far more than you wanted to, and, if you're still falling for his charm, eventually becoming responsible for his vast debts as well.

Watch out.

He'll run a mile

Freya, if you want to lose that 30-year-old, go ahead and give him the money for a downpayment on a flat. The sense of obligation can only emphasise the doubts he must have about a relationship with a woman so much older – and wealthier – than he is. Let him go on renting until the two of you discover whether what you have is permanent. If so, you can make the payment, and he can pay the mortgage from his good salary. What you don't want is to be a mother figure, buying sonny something to make him happy. Good luck.

Charles Alverson

By email

Keep your eyes open

I have to be honest with you. Are you mad? Please don't give your money to this man. I'm sure you really do love each other, but how well do you really know him? How well can you know anyone after six months ? I don't just say this because you are older than him, as I feel the age gap is irrelevant in this situation.

You mention that he has a good job, so clearly he isn't a bum who wanting to sponge from you, but I would seriously question his morals and motives if he expects a large amount of money from you.

If you are both truly in love with each other, then maybe consider you future together. I don't see any reason why you wouldn't have one. Maybe give the relationship another six months, then consider moving in together. Perhaps he could move in with you, or perhaps you could buy somewhere together.

Whatever you decide, just ensure that you protect yourself and your current assets. The fact that you are considering giving your boyfriend this money shows that your heart is wide open. Just be sure that you are eyes are too.

Shereen

By email

Don't be an old fool

Forgive me, Freya, but this hardly qualifies as a dilemma. He has a good job. He has not asked you for any money. If he truly loves you for yourself, he will not ask you – he will know that to do so will risk your relationship.

If he asks you, then frankly he is in it only for the money and, hard as it is, you must act accordingly.

Of course, things would be different if you were putting money into a home for both of you to share together.

Try to imagine the situation reversed – a 30-year-old woman and a single man in his late forties. Were he to part with his money in these circumstances and things were then to go wrong, many would be quick to say: "There's no fool like an old fool."

Peter Glover

Rayleigh, Essex

NEXT WEEK'S DILEMMA

Dear Virginia,

One of my best friends, who I've known since school, has has just learnt that he's got terminal cancer and has only been given a few months to live. I have written to him, obviously, and we've had long conversations on the phone. His main anxiety is his children, because their mother died two years ago. I've always been close to them – I've seen them grow up into lovely young people – and I wonder if I should write to them, expressing my sympathy? I am so fond of them and I want them to know that after their father dies there are still people around who care for them deeply.

Yours sincerely, Adam

What would you advise Adam to do? Email your dilemmas and comments to dilemmas @independent.co.uk, or go to independent.co.uk/dilemmas. Anyone whose advice is quoted will receive a £25 voucer from the wine website Naked Wines ( Nakedwines.com)