How to Commission D&D Art When You Don't Know Their Character (The Sneaky Gift Guide)
You want to surprise your boyfriend with a custom portrait of his D&D character for Christmas.
There's just one massive problem: you have absolutely no idea what his character looks like.
Or what race they are. Or if "warlock" is a good thing or a bad thing. Or what the difference between a longsword and a greatsword is, and frankly, you're not sure you care.
You've considered casually asking him about his character, but you're pretty sure "so what does your elf guy look like?" would immediately blow the surprise. He'd know exactly what you're planning.
So you're stuck. You want to give him this incredibly meaningful gift, but you're missing the one crucial ingredient: any actual information about what to commission.
Here's the good news: you have way more options than you think. And the best option doesn't require you to know anything about his character at all.
I've helped over 500 people commission D&D portraits, and at least half of them started in your exact position. "I know nothing and I need to keep it that way" is basically its own category of commission.
This guide walks through three proven approaches, from "complete secrecy" to "strategic intel gathering," so you can choose the path that works for your situation.
Understanding Your Three Options
Before we dive deep, here's the overview of what's actually possible:
Approach 1: The Photo Transformation (Zero Character Knowledge Required)
Commission a fantasy portrait based on his actual face. You send photos of him, choose a general fantasy vibe (warrior, wizard, rogue), and the artist transforms him into a fantasy hero. No character details needed whatsoever.
Approach 2: The Intelligence Mission (Sneaky Info Gathering)
Recruit allies (the DM, party members) or strategically gather information through careful observation. Build up enough details to commission his actual character without him knowing.
Approach 3: The Collaboration (Partial Surprise)
Tell him you want to commission character art and work together on the details. You lose the full surprise but gain certainty that it'll be exactly right.
Let's break down each approach so you can figure out which one fits your situation.
Approach 1: The Photo Transformation Method
(My Recommendation for Complete Secrecy)
This is the approach I recommend most often to gift-givers in your position, and here's why: it sidesteps the entire problem.
Instead of trying to figure out what his character looks like, you commission a fantasy portrait based on what he looks like. You transform his actual face into an epic fantasy hero.
How It Actually Works
Step 1: Gather Photos
You need 2-3 clear photos of his face from different angles. Ideally:
- At least one straight-on face shot
- Good lighting (not shadowy or backlit)
- Him looking relatively neutral (not mid-laugh or weird expression)
- Recent photos (from the last year or two)
You probably already have these on your phone. Candid photos work fine as long as his face is clear.
Step 2: Choose a Fantasy Aesthetic
You don't need to know his character's class or race. You just need to pick a general fantasy vibe that suits his personality or the kind of hero he'd want to be:
- "Fierce Warrior": Battle-ready, strong, commanding presence. Heavy armor, weapons, determined expression.
- "Mysterious Wizard": Mystical, intelligent, powerful. Robes, magical energy, knowing gaze.
- "Shadowy Rogue": Sleek, agile, dangerous. Leather armor, dual weapons, intense focus.
- "Noble Paladin": Heroic, righteous, protective. Shining armor, holy symbols, confident stance.
- "Wild Ranger": Rugged, outdoorsy, independent. Natural materials, bow, connection to nature.
If you're not sure, think about his personality in real life. Is he analytical and thoughtful? Wizard. Athletic and competitive? Warrior. Strategic and clever? Rogue.
Step 3: Work with an Artist Who Specializes in This
Not all commission artists do photo-based fantasy transformations. You need someone who:
- Specializes in taking real faces and rendering them in fantasy style
- Understands how to guide non-players through the process
- Can make decisions about fantasy details (armor style, weapons, colors) based on minimal input
The artist handles all the "D&D stuff." You just provide the photo and general direction.
Why This Approach Is Brilliant
Pros:
- Zero risk of getting character details wrong
- Completely secret—no suspicious questions needed
- Works even if he has multiple characters
- It's unmistakably HIM in fantasy form
- More personal in some ways than a character portrait
- No D&D knowledge required from you
Cons:
- It's not his specific character (if that matters to him)
- Won't match his character's race if it's non-human
- Requires good photos of his face
This approach is perfect for:
- Complete surprise gifts with zero info leaking
- When he has multiple characters and you don't know which to pick
- When you genuinely have no way to gather character info
- First-time commissioners who want minimal complexity
- When you want something deeply personal that's still fantasy-themed
The Reaction You Can Expect
Here's what typically happens when someone receives a photo-based fantasy portrait:
First, there's recognition: "Wait, that's me." Then there's the realization: "That's me as a fantasy hero." Then comes the emotional hit: "You turned me into the kind of character I imagine being."
It's different from seeing their specific D&D character brought to life, but it's powerful in its own way. Because it's not just fantasy art. It's them, transformed into the world they love spending time in.
I've watched this reaction dozens of times. The smile is always genuine.
Real Example: Sarah wanted to commission art for her boyfriend Marcus, who'd been playing D&D for two years. She knew he played "some kind of magic user" but that was it. She sent me three photos of Marcus and said "he's strategic and kind of mysterious, so probably wizard vibes?"
I transformed his face into a powerful wizard with dramatic lighting, mystical robes, and magical energy. When Marcus opened it on Christmas, his first words were "how did you make me look this cool?" It's been his Discord profile picture for over a year.
Six months later, Sarah told me: "He told his D&D group he loves it even more than a character portrait would've been, because it's actually him in their world, not just his character."
How to Get This Done
If this approach sounds right for you, here's what you need to do:
- Find 2-3 good photos on your phone (takes 5 minutes)
- Decide on general aesthetic (warrior/wizard/rogue/etc.)
- Work with an artist who specializes in photo-based fantasy portraits (I do this specifically for gift-givers)
- Provide photos + general direction ("make him a fierce warrior")
- Review the portrait when it's done (2-3 weeks typically)
- Give the gift and watch his reaction
That's it. No character sheets. No D&D terminology. No risk of getting details wrong.
For a complete breakdown of how fantasy portrait commissions work (including pricing and timelines), check out my guide to commissioning fantasy portraits as gifts.
Approach 2: The Intelligence Mission
(For When You Want His Actual Character)
If you're determined to commission his specific D&D character (not just a fantasy version of him), you need information. And you need to get it without blowing your cover.
Here's how to pull off the sneakiest gift reconnaissance mission of your life.
Strategy A: Recruit the Dungeon Master
This is your nuclear option. The DM (Dungeon Master) is the person who runs the game. They know everything about everyone's characters.
How to approach this:
Send them a direct message (Facebook, Discord, text, whatever works):
"Hey! I want to surprise [boyfriend] with custom character art for Christmas, but I need help. Can you tell me what his character looks like without him finding out? I'll totally owe you one."
Most DMs will be thrilled. They get just as excited about this stuff as the players do, and they love being part of a surprise.
What to ask the DM:
- "What does his character look like?" (physical description)
- "What kind of armor/clothing do they wear?"
- "What weapons do they use?"
- "What's their personality like?" (helps with pose/expression)
- "Any important accessories or items?"
The DM can usually answer all of this from memory or by checking their notes.
Pros:
- Most accurate information possible
- DMs love being part of surprises
- One conversation gets you everything
- You get the actual character, not a guess
Cons:
- You have to know who the DM is and how to reach them
- Slight risk they accidentally spoil it
- Won't work if he IS the DM
Strategy B: Enlist a Party Member
If you know any of the other players in his D&D group, they're perfect co-conspirators. They see his character every session and can provide detailed descriptions.
How to approach this:
"I'm commissioning character art for [boyfriend] as a surprise. Can you help me figure out what his character looks like? What do you picture when you think of [character name]?"
Players love this. They're invested in each other's characters and will happily help you nail the details.
Strategy C: The Eavesdropping Method
If he plays at home, you have a tactical advantage: you can just listen.
What to do:
During a game session, do something nearby (reading, working on your laptop, cooking, whatever). Casually listen to the game without making it obvious you're paying attention.
What to listen for:
- Physical descriptions: "My character walks up" "He draws his sword" "She adjusts her hood"
- Character name (they'll say it constantly)
- Race/species references: "As an elf, I..." "My dwarf beard..."
- Class abilities: "I cast fireball" (wizard/sorcerer), "I rage" (barbarian), "I use sneak attack" (rogue)
- Equipment mentions: "I pull out my bow" "I'm wearing my plate armor"
Take notes on your phone. Even fragments like "tall, dark hair, uses a bow" give an artist something to work with.
Strategy D: The Character Sheet Screenshot
If he tracks his character digitally (D&D Beyond, Roll20, etc.), you might be able to sneak a peek at his device.
Timing options:
- When he's in the shower
- While he's asleep (if he leaves his laptop open)
- When he steps away during a game session
What to screenshot:
- Character sheet main page (has name, race, class)
- Any character portrait/image he uses
- Equipment list
- Character notes or description field
Send these to yourself immediately and delete from his recent/sent items.
Ethical note: Yes, this is sneaky. It's also for a good cause (an amazing gift). Just don't snoop beyond what you need for the commission. We're being tactical, not invasive.
What If You Only Get Fragments?
Here's a secret: you need way less information than you think.
Professional D&D artists are used to working with incomplete details. If you come to them with:
- "His name is Theron"
- "He's an elf, I think?"
- "Uses a bow"
- "Wears green, I heard him mention that"
That's actually enough for an experienced artist to create something great. They'll ask clarifying questions, make educated guesses based on class/role conventions, and fill in gaps in ways that make sense.
I created a free resource called the Ultimate Character Blueprint specifically for this situation. It's a template that organizes character information into categories. You fill out what you know and leave blank what you don't. Then the artist can see exactly what information exists and what needs creative interpretation.
It transforms "I have random fragments of info" into "here's everything I know, organized clearly."
This approach is perfect for:
- When you want his specific character, not just a fantasy version of him
- When you have access to his DM or party members
- When he plays at home and you can observe
- When you're okay with a bit of detective work
- When accuracy to his actual character matters more than complete surprise
Approach 3: The Collaboration
(When Certainty Beats Surprise)
Some people just say "screw the surprise" and make the portrait commission a collaborative gift.
You tell him what you want to do, and you work together to make it perfect.
How This Works
Option A: The "Gift Certificate" Reveal
On Christmas morning, give him a card or printout that says:
"I'm commissioning custom artwork of your D&D character. Let's work together to make it exactly what you want."
Include example artwork from the artist you've chosen, or show him portfolio options. Make choosing the artist and providing details part of the experience.
Option B: The "I Tried But Need Help" Approach
Order the commission but tell him partway through:
"So... I tried to surprise you with character art, but I realized I don't know enough details to get it right. Can you help me make sure it's perfect?"
He gets to participate in the creation while still appreciating the thought and investment.
Why This Can Actually Be Better
Pros:
- Zero risk of getting details wrong
- He gets to be involved (which he might love)
- You still get credit for the thoughtfulness
- No stress or anxiety on your end
- Can discuss portrait type, pose, and details together
- He might reveal preferences you wouldn't have guessed
Cons:
- Loses the surprise element
- Less of a "Christmas morning reveal" moment
- Some people prefer full surprises
The truth? Many people end up preferring this approach. Yes, the surprise is gone. But the gift becomes a shared experience, and you're guaranteed he'll love the final result because he helped shape it.
This approach is perfect for:
- When you value certainty over surprise
- When he's particular about details and accuracy
- When you want to eliminate all stress from the process
- When making it a shared experience sounds appealing
- When you've already tried to gather info and hit dead ends
For a complete walkthrough of what the commission process looks like (whether you're working solo or collaborating), check out my first-time commissioner's guide.
The Decision Tree: Which Approach Is Right for You?
Answer these questions to find your path:
Question 1: How important is complete surprise?
- Critical (it must be a secret) → Approach 1 (Photo Transformation)
- Nice but not essential → Approach 2 (Intel Gathering) or Approach 3 (Collaboration)
- Don't care about surprise → Approach 3 (Collaboration)
Question 2: Do you have access to his DM or party members?
- Yes, and they'd help → Approach 2 (Intel Gathering)
- No, or I don't know who they are → Approach 1 (Photo Transformation)
Question 3: Does it need to be his specific character, or is "him as a fantasy hero" good enough?
- Must be his specific character → Approach 2 (Intel Gathering) or Approach 3 (Collaboration)
- Fantasy version of him works great → Approach 1 (Photo Transformation)
Question 4: How much effort are you willing to put into information gathering?
- Minimal (I want this to be easy) → Approach 1 (Photo Transformation)
- Moderate (I'll do some detective work) → Approach 2 (Intel Gathering)
- None (let's just work together) → Approach 3 (Collaboration)
Question 5: What's your confidence level with commissions?
- First timer, want simplicity → Approach 1 (Photo Transformation)
- Willing to learn and coordinate → Approach 2 (Intel Gathering)
- Want him involved to reduce risk → Approach 3 (Collaboration)
Real Success Stories (All Three Approaches)
Let me show you how each approach played out in real commissions:
Photo Transformation Success:
Jessica wanted to surprise her husband Mike for their anniversary. He'd been playing D&D for three years but had multiple characters across different campaigns. She had no idea which one to commission, and she wanted it to be a complete surprise.
She chose Approach 1. Sent me photos of Mike, said "he's analytical and strategic, so wizard vibes, but make him look powerful." I transformed his face into a commanding wizard with dramatic robes and mystical energy.
Mike's reaction: "This is me as the wizard I've always imagined being." It's been his work Zoom background for six months. Jessica said it felt more personal than a character portrait would have been.
Intel Gathering Success:
David wanted to commission art of his girlfriend Emma's ranger character, Lyra. He messaged her DM on Discord: "Help me surprise Emma with character art."
The DM sent him a full description: half-elf ranger, long chestnut braid, green leather armor, uses a longbow, has a scar across one eyebrow from her first hunt, personality is protective but warm.
With those details, I created a portrait that was exactly Lyra. Emma cried when she opened it on her birthday. She'd played Lyra for over a year, and seeing her come to life was overwhelming. The DM later told David the whole party wanted their own portraits now.
Collaboration Success:
Rachel ordered a commission for her boyfriend Chris but realized mid-process she didn't know enough details. She told him: "I already paid for character art of Theron, but I need your help to make it perfect."
Chris was thrilled. They spent an evening going through his character notes together, picking the perfect pose, and discussing every detail. Rachel said it became a bonding experience—she learned way more about his character and why D&D mattered to him.
The final portrait was perfect because Chris had input. And he still appreciated the gesture just as much as a surprise would have been.
Minimum Viable Information (For Approach 2)
If you're gathering intelligence, here's the bare minimum you need to commission something great:
Tier 1: Absolutely Essential
- Character's race (human, elf, dwarf, tiefling, etc.)
- General physical appearance (hair color, build)
- Class or role (warrior, wizard, rogue, etc.)
Tier 2: Very Helpful
- Clothing/armor style
- Primary weapon
- One distinguishing feature (scar, tattoo, unusual eye color)
Tier 3: Nice to Have
- Personality traits
- Color scheme preferences
- Specific accessories
- Pose ideas
If you have everything in Tier 1 and at least two items from Tier 2, you're golden. An experienced artist can extrapolate the rest.
What About Pricing and Timeline?
All three approaches cost roughly the same:
- Bust portrait (shoulders-up): $100-$200
- Half-body portrait (waist-up): $140-$250
- Full-body portrait (head-to-toe): $200-$400
The photo transformation approach (Approach 1) is sometimes slightly less expensive because there are fewer specific details to render, but the difference is minimal.
Timeline is also consistent: most professional commissions take 2-3 weeks from order to completion.
For detailed pricing breakdowns and what affects the final cost, see my complete guide to D&D commission pricing.
My Honest Recommendation
After helping hundreds of people through this exact situation, here's what I actually tell people:
If you want complete secrecy and simplicity, go with Approach 1 (Photo Transformation).
It eliminates all the stress, removes the risk of getting details wrong, and produces something deeply personal. The reaction is always powerful because it's unmistakably him, transformed into the fantasy world he loves.
Most people who choose this approach tell me afterward they're glad they didn't stress about gathering character information. The gift is just as meaningful—sometimes more so.
If his specific character is really important and you have access to his DM or party, go with Approach 2 (Intel Gathering).
The DM route especially is brilliant because you get perfect information in one conversation. If you can't reach the DM, the other intelligence methods work too, you just need to be more patient and strategic.
If you're okay sacrificing surprise for certainty, go with Approach 3 (Collaboration).
Don't underestimate this option. Many couples tell me the process of working on it together was valuable in itself. You learn about his character, understand why D&D matters to him, and create something perfect together.
Your Next Step
You're not stuck anymore. You have three solid paths forward.
If Approach 1 (Photo Transformation) sounds right—and for most people in your situation, it is—I've built a process specifically for this.
You send me photos. You tell me the general vibe. I handle all the fantasy elements and D&D stuff. Two weeks later, you have a stunning portrait that transforms him into an epic fantasy hero.
No character details needed. No D&D knowledge required. No risk of getting anything "wrong."
And because I know gift-giving is stressful, I offer a simple guarantee: if you don't love the first preview, you get your money back. No questions, no hassle.
Check out how the photo transformation process works, including examples, turnaround times, and pricing.
Or if you're still deciding which approach makes sense, read my complete guide to commissioning fantasy portraits as gifts. It covers everything from budget planning to presentation ideas.
The point is: you're not blocked anymore. You can give him this gift. You just needed to know you had options beyond "somehow learn everything about his D&D character."
Now you do.
— Jan