Friday Favourite: Holiday Shopping Skill Challenge

by Ameron (Derek Myers) on December 19, 2014

On Friday we comb through our extensive archives to find an older article that we feel deserves another look. From December 11, 2009, Dungeon’s Master once again presents: Holiday Shopping Skill Challenge.

‘Tis the season for giving and receiving gifts. Regardless of your personal or religious reasons for celebrating during the holiday season, everyone likes getting gifts. This is no secret to retail merchants. They know that you’ll be shopping for everyone on your list at this time of year and they want you to spend, spend, spend.

Shopping for Christmas presents can be a lot of hard, grueling work. It’s the part of the holidays that I like the least. So I decided to look at a challenging, real life situation through my D&D coloured glasses (as I so often do). A few months ago we put together a skill challenge called Battle for the Remote. It’s in that same vein that I present a holiday themed, real life skill challenge called Holiday Shopping.


There aren’t many shopping days left until Christmas. You’ve still got to pick up gifts for numerous people on your list. Priority should go to your wife’s gift if you know what’s good for you.


5 (12 successes before 3 failures)

I’ve never had a shopping experience of less than complexity 5, although some claim such a skill challenge does exist.

Primary Skills

Acrobatics, Diplomacy, Dungeoneering, Endurance, Insight, Intimidate, Nature, Perception, Religion, Streetwise

  • Each skill can only be used to accomplish 1 success towards the overall skill challenge unless noted otherwise.
  • Skill checks denoted as assist do not count as a success or failure towards the overall skill challenge.

Sample Skills

These are just a few examples of skills that can be used towards achieving successes in this skill challenge. Be creative. With enough cash any merchant (DM) will happily say yes.

Receive a +2 bonus to any social interaction skill if you smile. This stacks with all other bonuses.

Acrobatics (moderate DC)

Weave your way through the busy stores as other shoppers plod along, window shopping.

Diplomacy (hard DC +2)

Convince an over-worked, underpaid retail clerk to check the back for an item they’ve already told you is sold out. Receive a +5 bonus if you’ve ever worked retail and sympathize with them.

Dungeoneering (moderate DC)

Discover the best, most efficient way through the mall. Receive +2 bonus if you consult a directory.

Endurance (moderate DC, maximum 3 successes)

The mall crawl is tough work. An Endurance check is required for every hour spent in the mall or after visiting every 5th store.

Insight (hard DC)

Pick the best line when checking out. The shortest line isn’t always the best choice. Your instinct gives you a good feeling about a particular cashier.

Intimidate (moderate DC)

Threaten physical harm to another shopper if they don’t get out of your way or give up a present you were about to grab. Receive a +1 bonus for each hour you’ve been shopping and for every 5 stores you’ve already visited. These bonuses stack.

Nature (moderate DC)

Find out if it’s snowing now or will be later in the day and plan your trip accordingly. Receive a +5 bonus for consulting the weather channel.

Perception (hard DC, maximum 3 successes)

Spot a great deal.

Religion (moderate DC)

Pray that the gift you want isn’t sold out by the time you get there.

Streetwise (moderate DC, maximum 2 successes)

Ask a sales clerk when or if an item is going on sale. Receive a +5 bonus if you’ve ever worked retail and sympathize with them.

Streetwise (moderate DC, maximum 2 successes)

Talk to other shoppers and find out where the best deals are.

Thievery (hard DC)

Use of Thievery to steal gifts results in automatic failure of the skill challenge. Even if the check is successful you’ve ruined the original purpose for the gift giving. You should feel deep shame.


You did it. You got gifts for everyone on your list. You’re happy to be done and you know they’ll be happy to get these gifts. Another holiday shopping season is over.


You couldn’t find the gift you wanted and had to settle for something not on the list. It could go either way, but you’re pretty sure the outcome won’t be great. Worse yet, you got everything on the list but grossly misjudged someone’s desire to own that particular gift. Better luck next year.

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