Preheat the oven to 190°C, or 170°C fan forced.
Slice the top from the garlic head to expose the cloves. Drizzle with olive oil, wrap in foil and roast for 30–35 minutes, until soft and golden.
Allow the garlic to cool slightly, then squeeze the roasted cloves from their skins and mash into a paste.
Fry the finely diced streaky bacon in a large, heavy-based saucepan over medium heat until golden but still tender.
Transfer the bacon to a plate, leaving approximately 2–3 tablespoons of rendered bacon fat in the pan.
Add the sliced onions and a pinch of salt. Cook over medium-low heat for 30–35 minutes, stirring regularly, until deeply softened and caramelised.
Add the roasted garlic, thyme and rosemary. Stir for approximately 1 minute.
Add the bourbon and allow it to bubble for 1–2 minutes.
Return the bacon to the pan and add the dates, brown sugar, apple cider vinegar, maple syrup, balsamic vinegar, Worcestershire sauce, smoked paprika and water.
Simmer gently for 30–40 minutes, stirring occasionally, until the dates soften and the mixture becomes thick, sticky and glossy. Add a little extra water if necessary.
Season with freshly cracked black pepper and adjust the salt to taste.
Leave chunky or pulse briefly in a food processor for a smoother, spreadable consistency.
Divide between 6 clean, sterilised jars, allowing approximately 165–170 g per jar.
Cool and refrigerate. Because the jam contains bacon, it is not shelf stable. Keep refrigerated and use within approximately 5–7 days or freeze extra portions.
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