I won the lottery and took my family on a trip – they said I'm SELFISH

DEAR JANE: I won $1 million in the lottery and took my family on a five-star vacation to celebrate – they called me SELFISH because I didn’t give them all CASH

  • In her latest agony aunt column, best-selling author Jane Green gives advice to a recent lottery winner whose good fortune is causing a rift with his family
  • She also reaches out to a lesbian influencer who has fallen for a man
  • Do you have a question for Jane? Email [email protected] or ask it below 
  • READ MORE: I refuse to lie to my kids about Santa or buy them Christmas gifts

Dear Jane,

I was lucky enough to win a significant amount of money in the lottery a few months ago – just over $1 million. 

Sadly in today’s world, that’s nowhere near enough to allow me to retire anytime soon, but it’s enough that I can feel confident I won’t find myself falling on hard times. 

I tried to keep the win as quiet as possible, having heard all kinds of horror stories about past winners who suddenly found old acquaintances from high school getting in touch to ask for a handout, but I did tell my immediate family.

I also wanted to share the wealth, as it were, with my loved ones, so I planned a luxury vacation in the Bahamas for all 13 of us, complete with flights and a villa that I booked and paid for with my winnings.

The trip was amazing – but towards the end, it started to feel like some of my family members were expecting… more? They kept asking whether I had any ‘big surprises’ planned for the end of the trip, or whether I was planning to do something ‘over the top’ to bring the vacation to a close. 

Dear Jane, I won just over $1 million in the lottery and took my family on vacation to celebrate it – but instead of being happy for me, they called me ‘selfish’ for not giving them all cash

I took them all out for a nice dinner, but I kind of felt like I’d more than done my part by paying for the vacation in the first place?

When we got back home, I got an email from my aunt, which I thought would be a thank you message – but instead she revealed that she and several of my family members were ‘upset’ that I hadn’t shared the winnings with them in a more ‘generous’ way, essentially suggesting I should have given them all cash handouts.

Then my brother phoned me and said he thought it was pretty ‘selfish’ that I’d shoved my new money in their faces on this trip and wouldn’t it have been better for me to simply give them all money, so they wouldn’t have to feel ‘guilty’ about being on a trip that I was paying for. 

He also mentioned that several of them had been sharing similar grievances while we were away because they had been ‘expecting’ that I’d give them all cash to end the vacation.

International best-selling author Jane Green offers sage advice on DailyMail.com readers’ most burning issues in her Dear Jane agony aunt column

I am really pissed, I mean I spent tens of thousands of dollars taking them on vacation and that wasn’t good enough? A part of me wants to cut them all off for good with a flip of the bird, but then this guilty feeling creeps up inside me and I start to think maybe they were right?

Should I mail them all cash for Christmas and just be done with it?


Wary of Wealth

Dear Wary of Wealth,

My mother always used to use a phrase that immediately came to mind on reading your letter: no good deed goes unpunished.

I completely understand why you are angry. You did a lovely thing for your family, and instead of gratitude for an unexpected treat, they want more, which does not say anything particularly nice about them.

Wary of Wealth, you are not obligated to share your money with anyone. Imagine if one of the family members got an unexpected bonus at work. Would the rest of you be demanding their share? I think not. 

You got a windfall, and it’s yours, fair and square. Good God, people are their own worst enemies, aren’t they? Despite that, know that money does strange things to people, often revealing them at their worst.

You certainly don’t owe your family anything more. 

If you let them prey on your feelings of guilt, you’ll be left giving the whole lot away, and frankly, there’s nothing to feel guilty about. You’ve already done your bit. 

If they continue asking you for money, tell them you’ve put it in a trust (which is an excellent idea).

You’ve all enjoyed the luxury vacation. Don’t make the mistake of living like a drunken millionaire or you’ll be back at square one. Get yourself a financial adviser who can tell you the best way to protect that money so it doesn’t slip through your fingers, or the fingers of your family, like sand.

Dear Jane,

I’m a mid-20s lesbian with a relatively large following on social media. Most of my content is centered around sexuality and being gay, so I think it’s safe to say it plays a pretty big role in my life.

But a while ago at a gathering, I met a guy who does some work as a video editor. He knew who I was and thought my content was cool, and he even offered to help me out with some projects, which I happily agreed to since we seemed to get on well. 

We exchanged contact info, started talking frequently over the next few weeks, and quickly became good friends.

He’s a naturally flirty and charming guy, which I just found pretty sweet at first, but over time I started to get much more into him than I’d ever thought I could. 

He seemed to share my feelings, and eventually after meeting up at his place to work on some stuff together one day, we ended up sleeping together.

Dear Jane’s Sunday service 

The more inflexible we are in life, the more we try and keep things the same, keep the status quo, the more dull our lives tend to be. 

Stepping out of our comfort zones into the unknown can be terrifying, and gratifying, for that’s where the magic usually lies.

Now I’m not sure what to do… he’s a wonderful guy and I’m truly into him, and he’s into me too, but being a lesbian is such a big part who I am – as well as my job – so I’m not sure how possibly entering a relationship with a man would affect all of that?

Any advice would be appreciated!


Social Media Mess

Dear Social Media Mess,

If sexuality is a continuum, which most people seem to agree it is, then a certain amount of fluidity is to be expected. 

Of course there are plenty of people who find themselves firmly at either end, straight or gay, but far more people find themselves somewhere in the shades of grey. 

They may mostly be attracted to a particular type, be it male or female, then find, as you are discovering, themselves surprised.

I understand this is more challenging given that you make your living as a public lesbian, but the message of being open, of bravely finding yourself in a situation you never expected, of how you resolve that, and the challenges it brings, is important.

I suspect that being honest about this will resonate with many. For many people, sexuality is fluid. What draws an audience, whether it’s on social media, in books, in movies, is truth. 

People gravitate towards authenticity and truth, and whilst you don’t owe your followers anything, being truthful about the change, and how you feel about it, and the issues that arise, is important.

I urge you to bring your followers with you on the journey, remembering that what matters is not who you love, but that you love. I wish you much luck.

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