I'm a 59-year-old man just starting to date.

Ten years ago, I lost my business, my house, my marriage, and went bankrupt.

Today I have an excellent well-paying job and I’ve recovered mentally, but not financially.

I rent a house, own a nice car, but live paycheque to paycheque with zero savings. Though living very frugally I still can't get ahead.

I’m about to have a third date with a very successful executive woman. She’s complimented my good looks, witty conversation and strong work ethic.

When do I reveal my financial situation, or should I have already done so?

She’s five years away from retirement while I’ll have to work until I die. I don’t want a partner supporting me financially.

Is it unfair for an honest man with a nice car to hide his financial problems on the first date?

Poor Guy

Finances are interesting to early-daters, but honesty has a higher value.

Nevertheless, the first date is too soon to reveal your cash flow or lack thereof. You’re both just seeing if there’s any interest in each other.

The second date is also surface exploration – learning personality traits, comfort and attraction level.

The third date matters. Between mature adults such as you two, it becomes a statement of deeper interest.

Serious factors must be put on the table: Divorced/separated recently, or attached? Working/unemployed?

Finances? Tell the story matter-of-factly – your business failed; you expect to work indefinitely.

This woman will understand the impact of your current financial situation.

However, raising whether a future partner would have to support you in time, is conjecture, not fact. Do not present yourself as near-dependent.

Be open and stress the positives: you dug yourself out of major losses, mentally and practically. You’re building a new record.

She’s either interested enough to keep dating, or not. She may like you for yourself, and if so, may also have some helpful thoughts about your situation.

Just don’t let that topic take over getting to know each other a lot better.

FEEDBACK Regarding the ex-boyfriend who’d remained distant over months of dating and sleeping together, then suddenly texted her months later (December 17):

Reader – “Your response to this is clearly female-based. He wouldn't text for a fling knowing how it ended in the past.

“He didn't want to start big so he's just sending a greeting. Like everyone would do if they’re thinking of somebody who was in their life.

“You can do better.”

Ellie – I’m hoping that you can do better, too. Your approach to reading about relationships comes with gender-bias.

This guy did what many women have also done… led a person on with frequent dating and sex, while privately certain about never having a full-on relationship.

He also knew – just as women who behave this way, know – that his former “girlfriend” was devastated by his cold distancing.

No, I didn’t answer from a female perspective but from my view having spent years reading the painful, personal stories of many men and women, seeking advice when they’ve been rejected and devastated by lovers…. then casually approached later on, often when the availability of warm bed-partners gets too low.

This man’s a “user” - a personality characteristic which doesn’t have a specific gender-based gene.

That’s why I find periodic gender-based feedbacks like yours a wasted opportunity for readers to dig deep into an opportunity to learn what others feel.

All of us can do better in trying to understand each other.

FEEDBACK Regarding your Christmas Eve column advising people to feel the true seasonal spirit by helping out at a Christmas dinner for the homeless or a children’s hospital:

Reader – ‘The idea to help out is very good but not through a children’s hospital as most places with any vulnerable population require a police check and training.

‘I don't think they’d want anyone arriving to visit without permission from the families. Having unknown people visiting could compromise patient and family privacy and perhaps safety.

‘Perhaps you could’ve made it clearer that they can't just decide on Christmas Day to go somewhere to help out unless it’s already arranged with the organization.

‘Volunteering is a great way to help others and feel good about ourselves, too, but not by just dropping in.’

Ellie – Good point, thanks for catching me on that. I did assume, wrongly, that people interested in volunteering would check ahead, find out what’s acceptable, etc.