Money Diplomat

The right number for every money moment — tips, splits, gifts, salary

Navigate every awkward money situation with confidence. 18 scenario types covering tips, bill splits, Venmo requests, lending, dating, gifts, roommates, salary negotiation, inheritance, group travel, subscriptions, affordability checks, cultural money norms, charity, weddings, family, and coworker collections. Plus 5 bonus modes: instant tip/split calculator, debt tracker with AI nudge messages, conversation practice simulator, usage trends with charts, and a persistent profile so you never re-explain your budget or culture.

See what Money Diplomat gives you

Real output from an actual run on the bill below — an excerpt of a longer result, nothing reworded. The amounts are computed in code from the bill, so they add up to the cent.

The bill

Four of us at dinner: Ana, Ben, Cara and me. Ana and Ben shared a $48 bottle of wine and a $12 dessert that Cara and I never touched. Mains: Ana $24, Ben $22, Cara $19, me $21. Subtotal $146, tax $12.41. Everyone just assumes we're splitting the check evenly like always.

Real run, 2026-10-08, on a bill written for this page.

The awkward part

Cara and I would each overpay under the usual even split solely because Ana and Ben ordered a bottle of wine and a dessert the rest of us never had — roughly $22 for Cara and roughly $20 for me.

Equal split (total with a 20% tip: $187.61)

• Ana: $46.91
• Ben: $46.90
• Cara: $46.90
• Me: $46.90

Each pays for what they had, tax and tip shared in proportion

• Ana: $69.39
• Ben: $66.82
• Cara: $24.42
• Me: $26.98

How to bring it up

Hey, since Ana and Ben had the wine and dessert and the rest of us skipped those, should we just have them cover that part and split our mains separately? Probably easier than an even four-way.

Next time

Before the first order arrives, a quick 'should we split evenly or go by what we get?' takes ten seconds and prevents the whole awkward calculation at the end.

In a Nutshell

When

A money moment with a social edge — a tip, a split, a gift, a salary number.

You give

The situation type and the details. A saved profile sharpens everything.

You get

The right number, plus the words to say and how to handle the awkwardness.

The edge

It handles the etiquette as well as the arithmetic. Knowing the number isn't the hard part.

Good to Know

• Set your profile once and forget it — every situation response will automatically factor in your budget comfort level and cultural norms without you re-explaining each time
• Use Quick Math mode for the 60% of situations that just need fast arithmetic — save the AI-powered mode for socially complex scenarios where you need scripts and strategy
• The Practice simulator is especially valuable before salary negotiations and family money conversations — rehearsing with AI builds real confidence for the actual conversation
• Check Trends periodically to spot patterns — if you're constantly in 'lending' situations with the same person, the data makes it easier to set a boundary

Questions people ask

What is the fairest way to split a restaurant bill?

When everyone ordered about the same, split evenly — it is quick and nobody minds. When orders differ a lot, or some people shared things others did not touch, each person pays for what they had, with tax and tip shared in proportion to that. Shared items are divided among the people who shared them.

How much should I tip on a restaurant bill in the US?

For sit-down service in the US, 18–20% of the pre-tax bill is the usual range, and 20% is common in cities. Customs differ widely in other countries, where service may be included or tipping less expected.

How do I suggest not splitting evenly without being awkward?

Say it early and make it about the specific items, not the people: 'Since you two had the wine and dessert, want to cover that and we split the rest?' Before ordering is easiest; at the end, name the items and keep it light.

Does Money Diplomat do the maths for me?

Yes. When you list the items and prices, the split is calculated in code — shared items divided among the people who shared them, tax and tip in proportion — so the shares add up exactly to the bill. It also flags when the items you listed do not add up to the subtotal.