You rarely wait for company
Anyone watching would say you know how to enjoy yourself and rarely wait for company. With the North Node in Libra in the 5th house, delight is supposed to be shared: made with somebody, chosen together, witnessed. You need one pleasure that genuinely requires two people.
Solitary enjoyment is a real capacity and it has no second half. What is missing is the version where somebody else's pleasure is part of yours.
Make something with one other person
Start with a collaboration rather than a project: cook together, play together, build the thing with somebody whose hands are also on it. Then let them make half the decisions about how it goes. The output will be different from what you would have produced alone, which is the entire evidence you are collecting.
Sharing the making feels like it dilutes it
There is a specific reluctance about creative company: another person's choices seem likely to compromise the thing, so you would rather do it properly alone. Notice that you cannot know that in advance. Complete one collaboration all the way through before judging it. The compromise usually turns out to be an addition.
Enjoyment that has a witness
What accumulates is a store of shared pleasures rather than private ones: things you did with somebody, which both of you can bring up years later. Solitary enjoyment leaves no such record and is oddly hard to recall. The witnessed kind is what a life feels made of when you look back at it.
Going ahead because arranging it was slow
The retreat is impatience: coordinating with another person takes messages and delays, so you go alone and enjoy it perfectly well. Each individual instance is reasonable and the pattern behind them is the point. Wait for the arrangement once, even at the cost of losing the afternoon entirely. The waiting is the part being practised here.
Court somebody at their speed
Your romantic pace is yours: you decide, you move, and the other person is invited to keep up. It works on people who like being swept along and loses everybody else. Try one courtship conducted at their tempo, with their preferences leading. It will feel slow, and it produces a relationship rather than a conquest.
Joy that had somebody in it
Look back at the moments you would keep and count how many had another person present. If the good times are mostly solitary, that is not independence — it is a habit that has been quietly editing your life. Arrange three shared pleasures this season and notice which ones you are still thinking about in a year.
Co-author something
Creative work here has been signed by you alone, which is clean and limits what you can make. Take on one genuinely joint piece where the credit is shared and neither of you could have produced it. The negotiation is the difficult part and the result is usually beyond what either of you would have reached.
Let somebody else pick the fun
Your leisure runs on your own taste, so the people around you have never had much say in what you all do. Hand the choice over for a month — their film, their restaurant, their idea of a good Saturday. Enjoying something you would not have chosen is a specific skill and you have very little practice at it.
Play the game they wanted to play
With children your instinct is to introduce the activity, set the rules and run it well. Let them lead one entire afternoon instead, including the parts that are boring or make no sense. Being followed rather than directed is what they are actually asking for, and it is the harder half for you.