The Valentine’s Day Skill Challenge

by Ameron (Derek Myers) on February 14, 2012

Today is Valentine’s Day so we decided to take a light-hearted look at the day most associate with love. All the members of the Dungeons’ Master team are happily married or in a long-term relationship, so we felt that we should do our part to help those looking for love. However, we are by no means experts on the subject so please take the advice provided below with the good humour in which it is indented.

It’s unfortunate that many envision the gamer stereotype as a lonely guy who’s awkward around girls. Although there are certainly a few gamers out there that fall into this category, in my experience many gamers are not really that much different that the rest of the non-gaming masses. Everyone is looking for someone and hopes to avoid painful rejection along the way. With that in mind we’ve put together some tips in the form of a skill challenge. By framing this advice in a familiar wrapper we hope that it will make it easier for all those gamers looking for love on Valentine’s Day.

Skill Challenge – Looking for Love

Although love knows no bounds, this skill challenge is set up for young adults. That’s not to say that older folks won’t benefit from these tips, but those in their 20s are like to find this skill challenge a lot more familiar than those with more life experience.


You’re young in looking for love. Do you really need more of a setup than that?


Level will vary depending on your standards and whether you’re looking for a long-term commitment of just one night of fun and excitement.


Bluff, Diplomacy, Endurance, Insight, Stealth, Streetwise

Note: The DCs for these skill checks will vary considerably depending on the environment and the potential lover. Best to assume it will always be a hard check.


Many believe that lying is a tried and true way to impress girls. That’s not to say they believe the lies, but it’s a foot in the door and it gets conversation started. The bigger the lie the greater the chance of being shot down. However, even an outrageous and obvious lie can still have a positive outcome if you play it right.

Don’t forget to make that Bluff check when you’re getting dressed. The correct attire, or rather the appearance of the correct attire, can make all the difference.


For those who prefer a more honest approach there’s always straight-up Diplomacy. This usually requires incredibly confidence or a complete lack of shame. In either case honesty is often a better way to go. It’s always easier to remember the truth than some outrageous lie.

Diplomacy can also bee seen as the measure of courage. What you lack in finesse, you more than make up for in ambition.


Only the very fortunate few find a perfect match with their initial try. For the rest of us it’s a long and often tiring process which requires Endurance. Developing stamina can have additional benefits if you manage to find a receptive partner.


There are going to be times when she’s just not that into you. It doesn’t matter how good you are (or think you are). If she’s not interested then she’s not interested. It’s rare that you can change her mind once its made up. A strong Insight check will save you endless embarrassment, and let you know when it’s time to move on to a more receptive partner.


It’s easy to spot something beautiful; it’s difficult to see through the façade. In many social settings people go to great lengths to make themselves look more attractive than they really are (see Bluff above). Keep your eyes open and look for any tell-tale signs of significant manipulation.


In an environment rich with potential partners (a bar or night club, for example) men will often continue to look for love until they’re successful. It’s important that unsuccessful courting attempts are not seen by other women. It’s not that you don’t want to be seen, you just don’t want to be seen making the attempt or worse yet, striking out.


Finding the right woman can be difficult. Some men are content to settle, but those with more discernable taste will often take the time to survey the field before making any attempts at an introduction.

The Wingman

Never underestimate the importance or value of a good Wingman. His job is to assist you. With him on the scene you get an automatic bonus to most skill checks.

The Wingman should be skilled in Bluff, Perception and Streetwise. He’s your advance-man and the guy who helps you look better by comparison. He’s willing to talk to the less attractive friend or make other suitors look silly by comparison. Treat him right and your chances of success increase greatly.


Success is measured by the company you keep. If you’ve got someone then you win!


The consequence for failure in this challenge is another night alone. But the good news is that you can keep repeating this skill challenge as often as you want until you finally meet with success. Good luck!

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1 David Flor February 14, 2012 at 11:30 am

No use of the Intimidate skill? Even as an opposed check by the woman? 😉

2 Alton February 14, 2012 at 11:53 am

Your wingman can give you a +2 bonus to skill checks if he works it well.

The streetwise can be used to find the place with the types of people you would like to be with.

Cute article. I like it.

3 The Unlucky Paladin February 14, 2012 at 6:02 pm

Lol worth a laugh… Do you even do actual work at work bro?

4 Sunyaku February 17, 2012 at 6:23 pm

You could make this challenge a lot harder if the party knew that there was one Succubus/Incubus at the party to watch out for– or to put a less “datey” spin on this, the challenge could even be to find and lure the demons away from the party where they could be dealt with without anyone getting hurt.

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