Help Me Hera: How do I allow myself to enjoy frivolity again?

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I have to leave a perfectly good man because I want to be alone

This isn’t a question, so you’ve obviously made up your mind, but are presumably struggling with feelings of guilt or uncertainty. Sometimes it’s harder to leave someone who is undeniably good, but for whatever reason – timing or personal growth or an unsubstantiated but nagging sense of unease – your heart isn’t fully in it. It’s easy to feel like there’s something wrong with you for walking away from someone who, on paper, seems like a great partner. Who knows. There probably is. There’s something wrong with everyone. But this isn’t Regency England, and you’re not a downwardly mobile Austen character whose only chance of avoiding destitution is making a dull but economically sensible match.

Needing time alone in the world, to grow and challenge yourself and experience new things, is a completely legitimate and emotionally sound reason to end an otherwise good relationship. Besides, I can’t help noticing a conspicuous lack of enthusiasm. "Perfectly good" is the kind of descriptor you might use about an old microwave with a few years left on the clock, not the person you want to spend the rest of your life with. The best reason not to break up with someone is that you adore them and would miss them every day for the rest of your life. If you don’t feel strongly about your partner, and can’t help feeling like your life would be more rewarding alone, you owe it both to you to set them free, so you can both find a deeper happiness elsewhere.

How do I tell my parents that even though I have chronic health problems, I'm still almost 30 and an adult in my own right?

You can’t really tell people their perception of you is wrong, even if their perception of you is wrong. You can try, but it’s usually more effective to try and demonstrate your capability and independence through actions. But this is a long and tedious process, and people often stubbornly cling to an idea of you that doesn’t necessarily reflect your present reality.

I’m not a parent, but I assume it’s not an easy mental transition to make. After spending years of your life wiping someone’s ass and teaching them the alphabet, it must be hard to see them as anything other than your baby, even when they have mortgages and receding hairlines.

That’s not to say you just have to put up with whatever it is you’re putting up with, but it’s usually easier to address someone’s behaviour rather than their overall perception of you. If your parents are overbearing, it sounds like you need to set some boundaries, whatever that means for you. Maybe that means limiting their information, or access to your whereabouts/medical information, or whatever else is specifically driving you insane. If you’ve always had an overprotective family, this will be difficult, but asserting your independence and autonomy doesn’t have to be a negotiation.

Having said this, give your parents a little grace. No matter how old and capable you are, there is probably always a part of them that will secretly think of you as wearing a fuzzy duck romper, gorging yourself on handfuls of dirt.

My ex stole my bicycle

Your ex is a loser. You could try and steal it back in the dead of night, or file a probably useless police report, but honestly it’s probably not worth the drama/paperwork. Unless you have a profound sentimental attachment to the bicycle, or it was diabolically expensive, buy yourself a new bike and wash your hands of your ex. Sometimes it’s worth a hundred bucks never to have to see someone again. Hopefully they get a well deserved puncture.

After working effing hard to do all of the things I’ve been told I must do to have a sensible rest of life, how do I allow myself to enjoy frivolity again? I miss it.

Create a playlist that brings you joy, and blast it at tactical psychological moments.

Take up a few eccentric and cheapish hobbies, such as bedazzling furniture or inventing new kinds of cake.

Get a feather boa or an annoying and attention-seeking hat, and wear it to the supermarket.

Get a frivolous and joy-inducing pet, like a Jack Russell or a rat.

Buy a luxury cheese and eat alone it in the dark.

Take deliberate and conspicuous pleasure in meals, sleep and sunshine.

Sing loudly alone or in a group.

Spend time in nature.

Spend time in water.

Spend time with children and animals.

Live as if you have just been mistakenly released from a high-security vault, and may be discovered at any time. 

Remember you are an animal who must die.