Fun means scale, not comfort
With a Sagittarius Sun in the 5th house, enjoyment requires an element of size or risk: the long route, the ambitious project, the game where losing is genuinely possible. Comfortable entertainment leaves you flat within an hour. You need pursuits with some reach in them.
This is why your idea of a good weekend puzzles people who wanted a rest. Neither is wrong, and it is worth saying out loud before you plan a holiday with somebody for the first time.
What you make is made large
Creative work here arrives at ambitious scale: the long book, the piece requiring six people, the plan that needs three years. That reach is genuine and the completion rate is the weak point. Halve the scope of the next one deliberately and finish it, because one completed thing teaches you more than four magnificent outlines.
Romance as an expedition
You pursue people the way you pursue anything interesting: enthusiastically, with plans attached, and with an implicit invitation to come and see something. It is genuinely attractive. The gap is the ordinary Tuesday, when the expedition has ended and the person is still there wanting your attention on nothing in particular. That is the part you have to learn rather than the pursuing.
You will take the bet
Risk appeals to you as a form of play rather than as a calculation, and this is the house where that shows: the stake, the gamble, the venture entered for the interest of it. Set the loss limit before you start, in a number, and treat it as absolute. Your enjoyment does not require the stake to be large, only real.
With children you have permission to be ridiculous
Around children you are the adult who takes them somewhere, answers the enormous question honestly and is willing to look foolish. That is a rare gift and children remember it for life. The part needing effort is the smaller repeated care: the routine, the patience, the fifth reading of the same book without improvising a new ending.
Come and see this
Your courtship is an invitation into something larger, and it works because the enthusiasm is real. What sustains the relationship afterwards is different and less natural to you: staying interested when nothing is being discovered. Build one shared ongoing project, however modest, so that the two of you always have a horizon in common and the relationship never has to run on maintenance alone.
Work with an audience and a stake
Performance, teaching, entrepreneurship, anything where you are visibly attempting something with a real chance of failure suits you. Safe salaried repetition does not, whatever it pays. Choose the role with an actual wager in it, and keep enough behind you that a bad year is survivable rather than catastrophic. The reserve is what lets you keep taking the interesting risk.
The trip everybody still talks about
You are the person who proposes the outsized plan and then actually books it, which produces the occasions your friends recount for twenty years. Keep doing it and take one practical person with you. The vision is yours and the logistics are better handled by somebody who reads the schedule properly, which is a division of labour worth agreeing out loud before you book anything.
The parent who takes them out
Children in your orbit get expeditions, honest answers and the sense that the world is larger than the house. Balance it with something small and daily that they can rely on. A weekly ritual that never varies will mean more to a child than any of the adventures, though they will never say so.
Finishing one large thing
The satisfaction available here is completing something at genuine scale, which requires staying past the exciting stage several times over. Choose one ambitious project and give it a fixed end date rather than an open horizon. A deadline announced to other people is the only structure that survives your enthusiasm for whatever the next idea turns out to be.