Dear Vanessa,
I’m 54 and have been seeing a wonderful man who’s 58 for just over a year.
We both came out of long marriages and thought we’d finally found a second chance at love. He’s kind, generous, and emotionally supportive – everything I wanted.
The problem is, he’s still giving financial support to his ex-wife. It’s a significant monthly amount, and it’s been going on for several years. He tells me there are another five years left before it ends.
At first, I didn’t think much of it – after all, he’s doing the right thing and honouring his responsibilities. But over time I’ve noticed that when his business slows down, he struggles to keep up with the payments. He’s had to dip into savings and, more recently, I’ve started covering more of our shared expenses.
I pay for most of the dinners out, our weekends away, and even helped with some household bills when he was short. He insists it’s temporary, but I’m starting to feel uneasy.
I own my home outright and have worked very hard to build financial security. I love him, but I don’t want to end up carrying someone else’s financial load again.
Am I being cold-hearted, or just realistic?
Cautiously in Love.
Leading money educator Vanessa Stoykov
Dear Cautiously in Love,
You’re not being cold-hearted at all – you’re being wise, and you’re asking exactly the right questions. When we fall in love later in life, we often bring history with us – emotional and financial. It’s not easy to merge two lives that have already been lived.
Alimony, or spousal maintenance, is a legal obligation, and it can have a huge impact on how free someone is to build a new future. Your partner isn’t doing anything wrong by paying it, but what matters now is how transparent he is about his overall financial position and whether there’s a plan for stability.
If he’s repeatedly running short, that’s not just bad luck – it’s a pattern you need to understand before you entwine your finances any further. It’s also worth asking yourself some practical questions.
Is he contributing fairly to the relationship, not just emotionally but financially? Are you already starting to ‘rescue’ him when things get tight? Once that dynamic sets in, it’s hard to reverse.
Many women in their 50s and 60s end up in this situation – generous partners who slowly become the financial safety net. Love and money don’t have to clash, but they do need boundaries and clear expectations.
If you’re considering living together, I’d suggest having an open conversation about how bills will be split, what happens if his income drops again, and how you’ll protect your home and savings. A cohabitation or financial agreement drafted with the help of a professional can save a lot of pain later.
This isn’t about mistrust – it’s about self-preservation. You’ve worked hard for your security and protecting that doesn’t make you cynical; it makes you smart.
I strongly recommend sitting down with a financial adviser who can help you look at the numbers objectively and show you what the next few years might look like. You can find one here.
Relationships in midlife can be wonderful – full of maturity, laughter, and understanding. But the best ones are built on honesty and equality, not financial dependency.
Keep your eyes open, your heart steady, and your bank account separate until you both have a clear, shared plan for the future.
All the best,
Vanessa.