My friend keeps borrowing my money and NEVER pays me back

Dear Jane, 

My oldest friend is always in financial trouble and has asked me for money (again). She always promises to pay me back, but I’ve never seen a cent. 

I have always jumped in to help out, but now I’ve just discovered from another friend that my struggling pal has booked a luxury cruise trip for the pair of them and asked her not to tell me. 

I’m shocked, and hurt, and feel betrayed. She just asked for another ‘loan’, but she’s obviously using the money to secretly live a lavish lifestyle. 

What do I do? 

Love, Increasingly Poorer

Dear Increasingly Poorer,

My grandfather always used to quote Shakespeare: ‘Neither a borrower nor a lender be.’ 

In other words, don’t borrow money, and don’t lend it. What he meant was not that you should never help out a friend in need, as you have done numerous times, but that if you are going to help out financially, consider it a gift, rather than a loan.

Too many friendships have been ruined by money, and it’s fair to assume that someone who has got themselves into repeated trouble financially may have a hard time paying you back. If you are willing and able to help them financially, the only way forward is to let go of any expectations that you will be paid back.

Years ago I had a friend who was having a terrible time, and I knew that the financial stress on her was enormous. I never quite understood why she didn’t ever have money, but sent her a large amount – I was particularly flush at the time – which I suspected would get her out of the hole. 

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The first thing she said, after tears of relief, was that she would pay me back, but I never expected her to. 

In my head, this was a gift. Over the years I have seen her spend lavishly on things I would not spend money on in that position, but that is her choice, just as it was my choice to give her money with no strings attached. I recognized that it wasn’t my job to tell her where to spend her money, and when she spent it on designer handbags, I had to be okay with it. 

That said, I resolved that I would not lend money to that particular friend again, but would happily support her in other ways.

Which is the problem with giving money. If it’s a gift, it’s theirs to do with as they will. 

The bigger problem is your friend asking another to keep the cruise a secret. She knows she will be judged, but how much better it would have been for her to have been transparent? 

Who knows, had she come to you and said: ‘I haven’t had a vacation in years, I’m exhausted, I have no money, and I have this opportunity to go on a cruise, is there any way you can help me?’ perhaps you would have said yes, delighted at being able to help her out. 

That she is trying to hide this is deceitful. I suggest you sit down with her and say just that: had she been honest, you would have had a choice, but that you now feel betrayed by what she has done. See what she has to say, but I’m not sure a friendship can, or should, survive this kind of betrayal.

Dear Jane,

Last year I (amicably) divorced my husband of 26 years; there was nothing ‘wrong’ in our relationship per se, but over the years we grew apart and the spark we were lucky enough to enjoy for so long ultimately dimmed to nothing. 

At the encouragement of my friends I joined a few dating apps – just to see what was out there – and a few months ago I ended up connecting with a wonderful, handsome man… who just so happens to be 18 years my junior.

In so many ways, it’s been wonderful. He is attentive, passionate, energetic and he’s reignited my own sense of adventure. But at 49, I’m finding it incredibly difficult to get involved in his lifestyle. 

I don’t want to go out partying at bars with a group of 30-somethings until the early hours of the morning, and I certainly don’t find the prospect of a ‘10-person budget ski trip’ appealing – but I also don’t want him to think that I’m old and boring.

Is there a way I can prove that age really is just a number? Or am I stuck only dating older men for the rest of my life?

Love,

Aging disgracefully

Dear Aging Disgracefully,

It sounds like you’re already starting to think that this may not be the relationship for you, and I suspect, given your misgivings, this may be running its course. 

However, not for a second do I think you’re stuck dating older men. In fact, as far as I’m concerned, having almost hit the best decade of your life, you’re free to decide exactly what kind of relationship you want, and what works for you.

One of my dearest friends has been dating a wonderful man for the last five years, and they are quite sure that they will be together for life. 

Each of them has their own house, and although they spend some evenings, and nights, together, at least half the week she gets to go to her house, put on her softest pajamas, and climb into bed with a cup of tea, a stack of magazines, and a cat. Which she describes as ‘heaven’.

There are so many joys of aging – comfort in our skin, ability to say no, to decide what we will and will not tolerate in our lives. We care less what others think of us, and realize that we no longer have to people-please, that in fact, should we wish to be in bed by nine o’clock every night, we are absolutely entitled to forego bar-hopping and late-night parties. 

Every woman I know over the age of 45 is working on perfecting her Irish exit (leaving an event very quietly, without saying goodbye, and ideally, without being noticed). My ‘never again’ list includes futons, boxed white wine, and giant cruise ships.

As for being old and boring, look at style icon Iris Apfel – she’s 101 years old, as stylish as ever, and still bringing out new product lines! I defy anyone to call her old and boring.

This is less about age than about stage. It sounds like you may be at a different stage in your life, and you may ultimately want to find someone who shares similar interests and sensibilities. 

In the meantime, stop worrying about what anyone else thinks of you, Aging Disgracefully, for you have earned the right to live your life in the way you choose, regardless of what others think.