Halloween Date Raffle 2026

Guess who’s back… back once again, I couldn’t resist. And can you really blame me? It’s a little bit of fun and we all know I need that like a flower yearns for the sun.

The Halloween Date Raffle of course!

I know I said I wasn't doing one this year but this year has not gone to plan now has it. I’ve been bouncing around on the run up to this month whispering to myself ‘but I said I was doing a glasto and taking a year off from it’ & ‘those dates though… they’re always incredible and it really is fun to partake in’ and also, ‘it’s the dopamine, I need the dopamine, we all need the dopamine, why am I restricting dopamine in times like this?’ So, here we are. A little last minute and a bit more restrained with consideration to the past years events for me. Fun! Guaranteed, nonetheless.

Six lucky winners can win a date with me for 2027! Should you win the luck of the draw I am opening the diary for the winners to book in from February 2027 onwards. I know there is one winner from last year who is yet to claim his prize (Me! Obviously) - this year really threw a spanner in the works and made scheduling impossible. However now i’m back and the diary is open from February 2027 for winners, you are invited to book in for a date from then also! Or, should you wish to roll the dice again there is an upgrade on the table should the tide be once again in your favour.

What are the prizes, rules, important dates and participation fees I hear you ask?

There are six three hour dates up for grabs. Six winners with equal prizes but should someone win more than one then the prizes get added together. As you may know from past years, or incase you are new, I use a randomiser that is completely free from interference. Once all the entrants are in the hat it spins out the winners at random until six names are revealed and discretely noted.

The draw will be on the best night of the year, October 31st 2026 also known as All Hallows' Eve.

Tickets are £100 each and you can get more than one!

For this year only you can bundle buy SIX tickets at once (the amount of months I was forced into hiatus this year) for £300.

Every entrant that does not win has a choice this year on their consolation option, as years before everyone who doesn’t win can turn the ticket cost into a deposit/part payment on their next booking. Or they can request an original poem from me which can be as filthy, flirty, personalised and a little bit weird, as you like.

Let's have a little fun and get the diary for next year looking a lot more lively than this year has been!

All money raised is going towards the black hole my six month hiatus caused and the ongoing recovery of a concubine post crisis.

Enter by 6pm on October 31st

With Love,

Winter x

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