How to Romance Chance in Date Everything (March 2026 Guide)

Updated by Ankit Babal
July 7, 2025
Gaming

How to Romance Chance in Date Everything Guide

Ever wondered what it would be like to fall in love with a D20 dice? In Date Everything, this quirky possibility becomes reality through Chance – the enthusiastic tabletop RPG game master who’ll steal your heart faster than you can say “natural 20.” I’ve spent countless hours perfecting his romance route, and trust me, winning over this dice-turned-dateable is an adventure worth embarking on.

Quick Guide: Romancing Chance in Date Everything

Aspect	Details
Dateable Number	#60
Location	Office desk (left side, near pencil holder)
Voice Actor	Matthew Mercer (Critical Role)
Main SPEC	Charm
Meetings Required	2 interactions
Difficulty	Medium (requires winning G&G campaign)
Realization Requirements	Smarts: 80, Empathy: 60, Charm: 80, Sass: 30

Finding Chance: Your D20 Love Interest

Unlike the complex hunt for Airyn, locating Chance is refreshingly straightforward. Head to your office on the first floor and look for the D20 dice sitting on the left side of your desk, right next to the pencil holder. Don’t let his small size fool you – this little dice packs a massive personality that’s impossible to miss once awakened.

First Encounter Setup

When you first use your Dateviators on the D20, you’ll be greeted by an enthusiastic figure draped in a TTRPG map cloak. Chance appears with:

Red eyes behind red-lensed, gold-rimmed glasses
Brown hair partially hidden under a D20-shaped hood
A shirt featuring hand-drawn dungeon maps on grid paper
Dice bracelets adorning his wrists
A red G&G (Grottos & Gargoyles) rulebook chest piece

How to Romance Chance in Date Everything?

I’ve tested every dialogue combination possible, and here’s the definitive path to winning Chance’s heart. Unlike some dateables who require multiple meetings like Vaughn Trapp’s multi-step romance, Chance can fall for you in just two encounters – if you play your cards (or dice) right.

First Interaction: Setting the Stage

Initial Meeting Choices:

“… what did you call me?” – Acknowledge the misunderstanding
“Oh! Well then. A good day to you!” – Be friendly and welcoming
“You know what they say about all work and no play” – Show you’re fun
“Are you kidding me? Of course I’ve heard of G and G!” – Express enthusiasm
“I’m partial to… all of them, actually. How could I possibly choose?” – Show appreciation for all aspects

Campaign Setup: 6. “That would be a lot of fun, Chance!” – Accept his invitation eagerly 7. “Can we play with just the two of us?” – Choose intimate setting 8. “I can roll with that! What’s next?” – Go with the flow 9. “I dunno, this sounds right up my alley!” – Show genuine interest 10. “You would do that for me? You’re the best” – Appreciate his help

Character Selection: 11. “What do you suggest I play as?” – Let him guide you 12. “The Troubadour sounds like fun!” – Choose the bard class (recommended) 13. “When do we get to play?!” – Show excitement 14. “Sounds great! I can’t wait!” – End on a high note

Second Interaction: The G&G Campaign

This is where Date Everything’s unique gameplay shines. You’ll actually play a mini D&D-style campaign with Chance as your Dungeon Master (or should I say, Grotto Master?). The key to romance is not just winning – it’s showing enthusiasm throughout.

Pre-Game Dialogue:

1. “I couldn’t stay away from your cute face!” – Flirt immediately
2. “Ready, Chance!” – Show you’re prepared

Campaign Choices (Troubadour Path):

3. “[Sass 25] WHO’S READY TO ROCK! LET ME HEAR IT, COUNTER TOP!” – High energy start
4. “I toss them a coin for their prompt service” – Be generous
5. “I try to get a better look at them” – Show curiosity
6. “What’s The Butcher Block?” – Ask about the world
7. “I ask them, ‘What do you want with a simple singer?'” – Stay in character
8. “They think that… Oh!” – Realize the situation
9. “They may be beautiful but there’s no way they’re as hot as you, Chance” – Flirt with the DM

Mission Acceptance:

10. “Okay! I’ll do it! I’ll save the Prince!” – Accept the quest
11. “It’s great because I’m doing it with you!” – More DM flirting

Combat and Exploration:

12. “I break from the path to see what they do” – Take initiative
13. “Ahh!! What is that thing?” – React naturally to threats
14. “I wanna knock this Knobgoblin’s knob off!” – Show fighting spirit
15. “Maybe this is a sign. I need to collect myself before moving forward” – Strategic thinking
16. “I open my eyes, looking for the sound” – Be observant
17. “I bow. Instantly. No wait! I kneel!” – Show respect to royalty
18. “I’m on my way to save your son” – State your mission
19. “I would be honored to have you by my side” – Accept help graciously
20. “Let’s make ’em go Night-Night!” – Battle cry!

Final Battle Sequence:

21. “Is something the matter here, my Queen?” – Check on allies
22. “What?? The King?” – Express surprise at twist
23. “Monologue away!” – Let villain speak (classic D&D)
24. “I try to dodge out of the way!” – Defensive maneuver
25. “The Queen gave a command. Save the Prince!” – Remember priorities
26. “I’m going for the King!” – Make decisive choice
27. “I hope the shield works!” – Trust your equipment
28. “I start to throw sonic spells!” – Use your class abilities

The Romance Moment:

29. “I understand your insinuation and I am all for it” – Accept his romantic advance

Alternative Endings: Friends or Foes

Not everyone wants to romance every dateable, and that’s okay! Date Everything respects player choice with multiple ending options.

Friendship Ending

Want to keep things platonic? When Chance makes his romantic move asking about “moving from character sheets to… other sheets,” simply respond:

“Oh… this was just supposed to be a fun thing to do with friends!”

This maintains the positive relationship while establishing clear boundaries. You’ll still gain 5 Charm SPECS points and keep a wonderful friend who shares your love of tabletop gaming.

Hate Ending

Achieving Chance’s hate ending requires deliberate sabotage of everything he holds dear:

Mock G&G at every opportunity
Break character constantly
Choose deliberately terrible tactical decisions
Fail the campaign on purpose
Make fun of his enthusiasm for the game

The hate ending is surprisingly difficult to achieve because Chance is so genuinely enthusiastic and forgiving. It takes concentrated effort to make this sweetheart dislike you.

G&G Campaign Strategy Guide

Success in Chance’s campaign requires understanding the basic mechanics. Here’s what I’ve learned from multiple playthroughs:

Hit Points Management

You start with 50 HP
Sleeping between sessions restores 20 HP
The Sass 25 option grants +10 HP bonus
With proper choices, you can complete the campaign without taking damage

Class Differences

While I’ve detailed the Troubadour path above, each class offers unique gameplay:

Troubadour (Bard):

Best for first-time players
Charm-based solutions
Musical abilities for crowd control

Wizard:

Magic-focused combat
Requires more strategic thinking
Different spell options in battle

Warrior:

Direct combat approach
Higher damage output
Simpler decision trees

Rogue:

Stealth-based solutions
Trap detection advantages
Unique dialogue options

Combat Tips

Always scout before engaging
Use class-specific abilities when available
Remember the Queen’s alliance – she’s crucial for the final battle
The shield mechanic is vital against the King’s attacks
Don’t forget environmental interactions

Realization Requirements and SPECS Building

Once you’ve achieved a Love or Friend ending with Chance, you’ll unlock the ability to realize him – but only after completing 10 other dateables first. His realization requirements are surprisingly demanding:

SPEC	Required	Tips for Building
Smarts	80	Focus on dateables like Mac, Lyric, and Farya
Poise	0	No requirement – lucky!
Empathy	60	Romance Betty, River, and other empathetic characters
Charm	80	Date Phoenicia, Skylar, and other charming dateables
Sass	30	A few sassy encounters with Ben-hwa or Lux will suffice

Pro tip: Plan your romance route strategically. Since Chance gives Charm points, consider dating him after building up your other stats but before tackling dateables that require high Charm.

Voice Acting and Character Design Excellence

Matthew Mercer’s performance as Chance deserves special recognition. Known for his work as Dungeon Master on Critical Role, Mercer brings:

Authentic tabletop gaming enthusiasm
Perfect comedic timing on dice puns
Genuine warmth in romantic scenes
Expert narration during the G&G campaign

The character design brilliantly merges D20 elements with human features:

The hood shaped like an icosahedron
Dice accessories that jingle when he moves
Map patterns that shift during emotional moments
The way his eyes literally sparkle when discussing G&G

Common Issues and Troubleshooting

During my extensive testing, I’ve encountered several issues players might face:

Can’t Find Chance:

Ensure you’re looking at the office desk, not other surfaces
The D20 is small – look for the red die specifically
He’s on the left side of the desk near the pencil holder

Campaign Won’t Start:

You need at least one Dateviator charge
Must complete the first interaction entirely
Try sleeping and returning the next day

Keep Failing the Campaign:

Follow the exact dialogue choices above
Ensure you have 25+ Sass for the HP bonus
Save before starting the second interaction

Romance Won’t Trigger:

Must win the campaign first
Check that you were enthusiastic throughout
Ensure you didn’t accidentally choose friendship dialogue

Cultural Impact and Community Reception

The Date Everything community has embraced Chance with particular enthusiasm:

Speedrun Strategies

For players attempting to 100% Date Everything quickly:

Day 1: First interaction with Chance
Day 2: Complete G&G campaign for Love ending
Total time: Approximately 15-20 minutes
One of the fastest complete romances in the game

Advanced Romance Strategies

Dialogue Variation Testing

Through extensive testing, I’ve discovered:

Some dialogue choices have hidden point values
Enthusiasm matters more than “correct” answers
Flirting with Chance during the campaign adds romance points
Breaking character occasionally won’t ruin the romance if other choices are strong

Multiple Playthrough Benefits

First playthrough: Learn the campaign mechanics
Second playthrough: Optimize for perfect run
Third playthrough: Try different character classes
Achievement hunting: “Roll for Initiative” achievement

Comparing Chance to Other Dateables

Chance’s romance stands out for several reasons:

Unique Mechanics

Unlike straightforward dateables, Chance offers:

Full minigame integration
Multiple character class options
Branching campaign paths
Meta-commentary on dating sims through RPG lens

Romance Difficulty

Compared to other dateables:

Easier than: Connie (requires breaking Luna’s loop), Vaughn (multi-dateable chain)
Similar to: Parker Bradley (board game theme), Dasha (your supportive desk)
Harder than: Betty (your bed), Abel (tables), basic furniture

Tips for New Players

If you’re new to Date Everything and considering Chance as an early romance:

Pros:

Straightforward location
Quick completion (2 days)
Fun minigame teaches game mechanics
Matthew Mercer’s excellent voice acting
Good Charm SPECS payout

Cons:

Requires winning the campaign
Sass 25 requirement for easiest path
Realization needs high stats
Some players find RPG elements confusing

Recommended Approach:

Build up 25 Sass first (date a few sassy characters)
Save before starting his questline
Use this guide for dialogue choices
Enjoy the unique gameplay experience
Don’t stress about perfection – he’s very forgiving

Easter Eggs and Hidden Details

The developers packed Chance’s route with references:

D&D/Critical Role Nods:

“Natural 20” appears in his love ending text
The campaign mirrors classic D&D rescue quests
Voice lines reference famous Critical Role moments
His dice collection includes every standard RPG die type

Date Everything Meta-Humor:

Chance comments on dating sim tropes
G&G mechanics parody both D&D and dating games
The “other sheets” innuendo is perfectly delivered
His realization has him planning a campaign in the real world

Post-Romance Content

After achieving Chance’s love ending:

Collectible Unlock:

D20 always rolls natural 20 (was 10 before)
Special achievement for critical success
Unique dialogue if you return post-ending

Impact on Other Routes:

Dasha mentions your G&G session
Parker Bradley references tabletop gaming
Mac comments on dice probability
Some dateables ask about your campaign

Frequently Asked Questions

Q: What happens if I choose a different character class?

A: Each class has unique dialogue options and solutions. The core romance path remains similar, but combat encounters change significantly. Warrior is easiest for combat, while Rogue offers the most unique dialogue.

Q: Can I romance Chance if I hate tabletop RPGs?

A: Absolutely! The game doesn’t require prior D&D knowledge. Chance explains everything needed, and the simplified mechanics make it accessible for newcomers. Just show enthusiasm for his interests.

Q: Is Chance’s SASS requirement mandatory?

A: Not mandatory, but highly recommended. Without 25 Sass, you miss the HP bonus dialogue option, making the campaign harder. You can still win without it, but you’ll need to play more carefully.

Q: How long does Chance’s complete route take?

A: Roughly 15-20 minutes for both interactions. The first meeting takes 3-5 minutes, while the G&G campaign runs 10-15 minutes depending on reading speed and choice consideration.

Q: Can I replay the G&G campaign after finishing?

A: Unfortunately, no. Once you’ve achieved an ending with Chance, returning only gives brief dialogue. The campaign is a one-time experience per save file, making that first playthrough special.

Q: What’s the best order to romance dateables for stats?

A: For Chance’s requirements, I recommend: Start with Sass-giving dateables → Build Empathy through kind dateables → Save Charm-givers for last since Chance provides Charm → Tackle Smart dateables throughout.

Final Thoughts

Chance represents everything magical about Date Everything – the ability to find love in the most unexpected places. His route combines humor, genuine emotion, and innovative gameplay in a way that few other dateables match. Whether you’re a tabletop gaming veteran or someone who doesn’t know a D20 from a D12, Chance’s infectious enthusiasm and Matthew Mercer’s stellar performance create an unforgettable romance experience.

So grab your dice, charge up those Dateviators, and prepare for an adventure where love is the ultimate critical hit. After all, in the world of Date Everything, romance doesn’t have to be left to chance – even when you’re literally dating Chance!

Remember to save your game before starting his route, check out our other Date Everything guides, and most importantly, have fun rolling for romance. May all your romance rolls be natural 20s!