Design Your Dating Life: Five Free Worksheets (PDF Pack)

Dating is a design problem, not a lottery

Ask a successful man how his last project at work succeeded and you will get a structured answer: a brief, constraints, feedback loops, reviews. Ask the same man how his dating life is going and you get weather-report language — "quiet lately", "you know how it is", "the apps are dreadful". One area gets his intelligence; the other gets his leftovers.

The premise of this pack is simple: your dating life responds to the same discipline as everything else you are good at. Not tactics, not scripts, not pretending to be someone else — just honest data about what you want and what you are doing, reviewed on a schedule, with small experiments instead of grand resolutions.

Worksheet 1: The Dateview

The Dateview is 250 to 500 words of continuous prose answering one question: what is dating actually for? It is the counterpart to the original course's Workview, and it is harder than it sounds, because the honest answer is rarely the respectable one.

Write in paragraphs, not bullet points — bullets let you hide. Answer the prompts inside the writing: why date at all, beyond not being alone? What kind of relationship do you actually want, as opposed to the one that sounds impressive at dinner? What do you bring? What will you not negotiate on — and what have you been filtering on that would not matter in year five?

The mistake to avoid is writing the version you would say at the pub. Nobody sees this page. If the truthful answer is "I want someone who makes the house feel different when they are in it", write that. You cannot design around a lie.

Worksheet 2: The Lifeview

The Lifeview asks the wider question: what life do you want in three years? Write it on a different day from the Dateview, so the two are not quietly reconciled in your head before they reach the page.

Be concrete. Describe an ordinary Tuesday evening three years from now — who is there, what is cooking, what time people leave. Describe a good weekend. Describe where you live and how work fits around life rather than over it. Vague criteria produce vague results; a specific picture gives you something to steer by.

Then comes the exercise that makes both pages earn their keep: read the Dateview and Lifeview side by side. Underline where they support each other, circle where they contradict. The man whose Dateview says he wants a settled relationship and whose Lifeview describes seventy-hour weeks and four work trips a month has just located his real problem — and it was never his Hinge profile.

Worksheet 3: The Good Date Journal

For two to three weeks, log every date and every social evening where you met new people. Four columns: the date and setting, how engaged you felt from one to ten, whether the evening gave or took energy, and one line on what specifically was good or bad.

This feels too simple to matter. It matters because memory lies in your favour. Men are certain they "never meet anyone" until two weeks of data show three evenings they cancelled and one they left early. Others discover the pattern is not the women but the format — dinner interviews drain them, while the climbing-wall introduction their friend organised left them energised even though nothing romantic came of it.

At the end of each week, answer the three reflection questions on the sheet: which settings keep producing high-engagement evenings, what drains you regardless of who was there, and what gets more time next week. That is your dating strategy writing itself from evidence.

Worksheet 4: The Meeting Map

Once the journal has data, take one moment where you felt genuinely at ease with someone new — not the most successful moment, the most natural one — and put it in the centre of the page. Branch outwards without editing: places, activities, people, atmospheres. Push past the obvious first ring; the interesting options live in the second and third.

Then compress the map into three channels. One recurring weekly commitment where the same faces return, named with a day and a time. Three people in your existing network who could introduce you to someone, named, with the message you will actually send. And the one app you keep, with a strict weekly limit — the rest get deleted.

Three channels is the whole architecture. It replaces the vague intention to "get out there more" with a week that has specific doors in it.

Worksheet 5: Three Dating Futures

The final worksheet is the dating version of the Odyssey Plan, and the one to do if you do only one. Sketch three genuinely different three-year futures. Future A is your current approach extrapolated — same apps, same week, same effort. Future B: the apps are deleted tomorrow and cannot come back, so what do you build instead? Future C: fear and other people's opinions are removed — what would you actually do?

Give each future a six-word title, a few lines of what has to happen, and honest scores out of five: realistic, exciting, confident, coherent with your Dateview and Lifeview.

Most men arrive certain that Future A is sensible and Future C is fantasy. They finish realising there is at least one piece of B or C that could be pulled into next month — a recurring thing to join, an introduction to ask for, a conversation to stop avoiding. The last line of the sheet asks you to write that piece as a dated action, because an insight without a date is a nice evening's entertainment.

How to actually use the pack

Print it. Block one quiet hour for the Dateview, a separate one for the Lifeview. Run the journal for a fortnight before you judge anything. Do the Meeting Map with the journal in front of you, and give the Three Futures a proper ninety minutes rather than a rushed twenty.

Two warnings from watching men do this work. First, do not fill the pack in once and file it — the value is in the review, so put a date in your calendar to re-read it in a fortnight. Second, do not use the worksheets as a sophisticated way to delay action. The pack takes a month at most; at some point the journal has to record real evenings with real people.

If you finish the pack and want a second pair of eyes on what it surfaced, that is exactly what the free thirty-minute call is for. Bring the sheets — the contradictions you circled are usually where we start.